How to Take Intelligent Career Risk (and Win Mentoring from Reid Hoffman, Chairman of LinkedIn)

climb at your own risk

(Photo by graziedavvero)

The following post is co-authored by Ben Casnocha and Reid Hoffman. In the conclusion, there is a once-in-a-lifetime opportunity to be mentored by both of them.

Ben Casnocha is an award-winning author and serial company-builder, whom BusinessWeek has labeled “one of America’s best young entrepreneurs.” Reid Hoffman is Co-founder and Executive Chairman of LinkedIn, a Partner at iconic venture capital firm Greylock Partners, and #3 on Forbes’ 2012 Midas List. Last but not least, he’s often referred to in Silicon Valley as “The Oracle” for his seemingly prescient start-up-picking abilities…

Ben and Reid are the authors of the #1 New York Times bestseller, The Start-Up of You: Adapt to the Future, Invest in Yourself, and Transform your Career, which argues that everyone should apply the principles of entrepreneurship to their lives, even if they never plan on starting or running a company.

Enter Ben and Reid

Roll the clock back 15,000 years and play through two scenarios in your mind.

Scenario 1: It’s nearly dusk and you’re sitting on a fallen tree to rest. Suddenly you hear some rustling in the brush behind you. Instinctively, you shoot your head around. Your eyes dart back and forth searching for the source of the noise. It’s quiet for a few moments and you hear your heart pounding in your chest. Unsure what caused the noise, you spring to your feet and decide to run back to safety with the rest of your tribe.

Scenario 2: You’re walking along a dirt trail near the river. Far across the water you see the carcass of a recently killed deer. It could provide several days worth of meals but traversing the river would be arduous and time-consuming. The sun has set and if you misjudge the water depth, you might be swept away and unable to find your way back in the dark. You decide it’s not worth the trek.

Both of these decisions make sense in their own way: If you choose to stay in the woods and the rustling noise is a hungry wolf, you’re dead. If you skip going after the deer carcass, you’re not going to starve. You’ll find other food or another tribe member will. This logic is ingrained in our brain: It’s more costly to miss the sign of a threat than to miss the sign of opportunity.

The world has changed, but our brains have not

We live in a different world than that of our ancestors. We do not sit around fires and wander forests in search of food. Civilization has changed greatly, but our brains have not.

Evolution via natural selection shaped the human brain over millions of years to achieve a simple goal: stay alive long enough to reproduce and raise offspring. As a result, we react faster, stronger, and harder to threats and unpleasantness than to opportunities and pleasures. There’s a red alert in our brain for bad things, but no green alert for equivalently good things. Sticks get our attention and carrots do not, because avoiding sticks is what mattered to staying alive.

Neuropsychologist Rick Hanson sums up this “negativity bias” nicely:

“To keep our ancestors alive, Mother Nature evolved a brain that routinely tricked them into making three mistakes: overestimating threats, underestimating opportunities, and underestimating resources (for dealing with threats and fulfilling opportunities).”

Overestimating risks and avoiding losses is a fine strategy for surviving dangerous environments, but not for thriving in a modern career. When risks aren’t life-threatening, you have to overcome your brain’s disposition to avoid survivable risks. In fact, if you are not actively seeking and creating opportunities—which always contain an element of risk—you are actually exposing yourself to more serious risks in the long term.

What kinds of career risks should you take?

Risk is personal—what might be risky to a friend may not be risky to you. It’s also situational—what may be risky in one situation may not be risky if the circumstances are slightly different. But for anyone and everyone, a risk is good when the possible upside outweighs the possible downside, when the reward justifies the risk.

“All courses of action are risky, so prudence is not in avoiding danger (it’s impossible), but calculating risk and acting decisively.” – Machiavelli

Indeed, risk is an unavoidable constant of life, so your focus should be on taking the right kinds of risks that offer the right kind of opportunity.

The problem is the negativity bias — we tend to exaggerate the riskiness of certain moves and underestimate the opportunities of others. Here are some examples of frequently overstated risks, along with their associated opportunities:

Jobs that pay less in cash but offer tremendous learning.

People focus on easily quantifiable hard assets—like how much they’re getting paid in cash. But soft assets—knowledge, connections, and experiences—matter more when you’re younger. Jobs that offer less cash but more learning are too quickly dismissed as risky.

– Internships

– Apprenticeships

– High-level assistantships

Part-time gigs that are less “stable” than full-time jobs.

Many dismiss part-time gigs and contract work as being inferior to full-time jobs. But in reality, doing contract work is a terrific way to build the skills and relationships that help you pivot into the next opportunity.

– Freelance writing

– Programming

Working with someone with little relevant experience but high learning clock speed.

Fast learners make up for their inexperience in spades. The flip side of inexperience often is hustle, energy, and a willingness to learn.

– Taking a chance on a smart, scrappy person just out of college

– Partnering with someone mid-flight in a career who’s pivoting into a new industry and feeling re-energized by the challenges

An opportunity where the risks are highly publicized.

The more we hear about the downside to something, the more likely we are to overestimate the probability that it will occur (this is why people tend to become more afraid of flying after news of a plane crash is splashed across the headlines). If the media, or people in your industry, talk a lot about the riskiness of a certain job or career path, it probably isn’t as risky as most believe, and that means there’s less competition for landing the opportunity.

– Starting a company

– Working in a high tech industry

Overseas adventures.

International career opportunities involve uncertainty. There may be confusing cultural nuances or low transparency in the government. Spending time in other countries “feels” risky in part because when you’re not from a place, you initially do not understand much of the day-to-day life around you. But the best opportunities are frequently the ones with the most question marks. Don’t let uncertainty lull you into overestimating the risk. As Tim says, “Uncertainty and the prospect of failure can be very scary noises in the shadows. Most people will choose unhappiness over uncertainty.” This is true, and especially worth remembering when contemplating an international adventure.

– Foreign assignment within your company

– Attending a conference or seminar in another country

– Volunteering overseas

In all these opportunities, the worst case scenario tends to be survivable. When the worst case of a given risk means getting fired, losing a little bit of time or money, experiencing some discomfort, etc., it is a risk you should be willing to take. By contrast, if the worst-case scenario is the serious tarnishing of your reputation, or loss of all your economic assets, or something otherwise career-ending, don’t accept that risk. Asking yourself whether you can tolerate the worst case scenario is a quick and dirty way to size up risk in situations where you don’t have much information or time.

How often should you be taking risks?

If you’re reading this blog, chances are you encounter situations of risk often.

Working remotely, say, or self-experimenting with unconventional diets and blood tests. These sort of exploits introduce risk into your life in the way of volatility and uncertainty, but they are not necessarily risky things to do. The risk level doesn’t cross a threshold so as to become irrational. In fact, by pursuing new opportunities like these all the time (and accepting their associated risks), you are actually creating career stability for yourself.

Traditionally, people hold the opposite view. In 2004, two economists estimated the riskiness of working in different industries, according to the consistency of income streams and average unemployment levels of people in those careers. They referred to income fluctuations, including bouts of unemployment, as “shocks.”

By their account, risky careers (more severe shocks) included:

– Business

– Entertainment

– Sales

Non-risky careers (less severe shocks) included:

– Education

– Health care

– Engineering

The risky careers were thought to be more volatile, full of regular risks and issues, and non-risky careers were thought to be more stable. Risk-averse people are teachers, doctors, and lawyers. Risk-takers may be starting companies or trying out on Broadway.

But it’s exactly the opposite.

A low risk career is “stable” in the way a country like Syria or Saudi Arabia is stable. Dictatorships do not allow much day-to-day volatility, but when there is a fire, it can quickly turn into major chaos or even revolution. By contrast, Italy has been dealing with constant political turmoil for centuries, and has experience in responding to unexpected crises. As Joshua Ramo explains, Italy is resilient to dangerous chaos because it has absorbed frequent attacks, like “small, controlled burns in a forest, clearing away just enough underbrush to make [them] invulnerable to a larger fire.”

In the short term, low volatility means stability. Over the long run, however, low volatility leads to increased vulnerability, because it renders the system less resilient to unthinkable external shocks.

This paradox—high short-term risk leads to low long-term risk—holds true for your career.

Fragile careers vs. Resilient careers

IBM, HP, General Motors— stalwart companies that have been around a long time and employ hundreds of thousands of people. At one point in their history, each of these companies had de facto (or even explicit) policies of lifetime employment. They were the stable employers of yesterday.

While today’s employers don’t offer lifetime employment, a handful of industries still offer some semblance of stability: it’s relatively hard to be fired, your salary won’t fluctuate much, and your job responsibilities stay steady. These are the careers generally deemed less risky: government, education, engineering, health care.

But compare someone working full-time in state government to an independent real estate agent. The real estate agent doesn’t know when his next paycheck is coming. He has ups and downs. He has to hustle to build a network of clients and keep up with changes in the market. His income is lumpy, and sporadic big wins (selling a multimillion-dollar home) keep him alive. The government worker, by contrast, gets a steady paycheck and an automatic promotion every couple years. He always eats well . . . until the day comes that government pensions explode or austerity measures wipe out his department. Now he’s screwed. He will starve because, unlike the real estate agent, he has no idea how to deal with the downs.

Or compare a staff editor at a prestigious magazine to a freelance writer. The staff editor enjoys a dependable income stream, regular work, and a built-in network. The freelance writer has to hustle every day for gigs, and some months are better than others. The staff editor is always well fed; the freelance writer goes hungry some days. Then the day comes when print finally dies. The industry crumbles, the magazine folds, and the staff editor gets laid off. Having built up no resilience, he will starve. He’s less equipped to bounce to the next opportunity, whereas the freelance writer has been bouncing around her whole life—she’ll be fine.

So which type of career is riskier over the long run?

Today’s world is full of change and unpredictable disruption. Unless you take frequent, contained risks, you are setting yourself up for a major dislocation at some point in the future. Inoculating yourself to big risks requires taking small, regular risks—it’s like doing controlled burns in a forest. By introducing regular volatility into your career, you make surprise survivable. You gain “the ability to absorb shocks gracefully.” You become resilient as you take risks and pursue opportunities.

Take, for instance, moving to Santiago, Chile for nine months.

I hoped an international living experience (distinct from a travel experience) would jog new sorts of learning and opportunity. I went to Chile with no set plan, no fluency in the language, and never having lived in another country outside of the US. I had butterflies in my stomach when I was packed my bags. There was immense uncertainty. I swallowed through that uncertainty on the faith that the cultural stimulation alone would be worth it, even if my social/professional/linguistic goals weren’t realized.

Looking back now on those nine months, it was an unmatched growth experience for me.

What will be your unmatched growth experience?

Final thoughts from Reid

For my first job after grad school, Apple hired me into their user experience group. Shortly after starting on the job, I learned that product/market fit—the focus of product management—actually mattered more than user experience or design. You can develop great and important user interfaces, and Apple certainly did, but if customers don’t need or want the product, they won’t buy. At Apple, and in most companies, the product/market fit questions fall under the purview of the product management group, not user experience. And because product management is vital in any product organization, work experience in the area tends to lead to more diverse career opportunities.

I attempted to iterate into a product management role within Apple. But the product management jobs required product management experience. It’s a common catch-22: for jobs that require prior experience, how do you get the experience the first time?

My solution: do the job for free on the side. I sought out the head of product management within the eWorld group at Apple and told him I had a few product ideas. I offered to write them up in addition to everything else I was doing, and I did. It was a risk: my boss could have been annoyed I wasn’t focused on my existing responsibilities; given my lack of experience, there was a decent chance the product ideas I wrote up were going to be bad, thus making a bad first impression to product folks within Apple; my youthful proactiveness could have been seen as naïve brashness.

But the risk worked out in the end–I got good feedback on my moonlit product plans, and I ultimately acquired enough experience to land a full-time product management job at Fujitsu after Apple. Of course, not all risks work out—but this story of volunteering-to-do-extra-work sticks with me as a career risk I am very happy I sought out, as it set in motion a series of other key opportunities.

[On one other risk that paid off]

I joined the board of PayPal while I was working at Socialnet, my first company. Normally entrepreneurs are told to maintain extreme focus on their company and day job, so joining a board of another company at the time was a risk. I establishedprotocols with Peter and Max to make sure the PayPal commitment wouldn’t interfere too much with Socialnet – e.g. I promised to them back by midnight if they had questions, which meant discussion in the evening hours, not 9-5 normal workday hours. As it turned out, Socialnet was soon to be winding down operations so I pivoted to work at PayPal full-time in January, 2000. The board position risk proved wise in hindsight because, in addition to being a learning opportunity in its own right, it set me up for a full pivot to Plan B. In other words, the PayPal side-project risk meant I traded down on focus in exchange for a broader set of learnings and increased mobility for my next career move.

4 keys to becoming a more resilient, intelligent risk taker

1. Remember your negativity bias will cause you to exaggerate your evaluation of certain risks. Whatever it is you’re thinking about doing, there’s probably not as much risk involved as you think.

2. Identify—and take on—risks that are acceptable to you, but that other people tend to avoid. Are you okay having less money in savings and taking a low-paying but high-learning job? Or maybe a month-to-month employment contract as opposed to something longer term? Go find a project with these sorts of risks. It will differentiate you from others.

3. Say “yes” more. What would happen if you defaulted to “yes” for a full day? A full week? If you say yes to the conference invite you were tempted to skip, might you overhear a comment that ignites your imagination for a new business or new research or a new relationship? Perhaps. Might it also lead to some dead ends, mishaps, and wasted time? Sure. But trying new, small things every day introduces regular risks that, over time, build up your resilience to big disruptions.

4. Now it’s your turn. Leave a comment on this post, introduce yourself, and tell us:

– What change do you want to make in your career in the next 30-60 days? (e.g. Change jobs, ask for a raise, find a new opportunity within your company)

– How are you thinking about the risk involved in this move?

We’ll select the person who leaves the most thoughtful comment no later than 5pm PST, June 21 (Thursday), and personally invest in making that person’s next career move successful. 

Here’s what we can offer:

– Over email and in a 30-minute phone call, we’ll suggest relevant opportunities, key people to meet, and provide motivational support. The initial 30-minute call will be with me (Ben), and the follow-up emails will include Reid.

– Two signed copies of The Start-Up of You.

– Your story will be highlighted in our LinkedIn Group.

– Free Linkedin Premium subscription

Think of this as a personalized high-impact session on how to take your next best step by embracing (or creating) the right types of risk.

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Odds and Ends: App Contest Winner

Chad Mureta has chosen the winner of the app contest in his previous how-to post on building an app empire. Thanks to all for your submissions! Here’s his announcement:

The winner of the contest is Alex Kourkoulas. His app idea: “Legend: Put meme-like captions on your photos and share them with friends.”

Our top two favorite runner-ups:

Dina S. Her app: “Teacher Text: Quick, easy SMS communication with teachers. Students can text questions about homework, quizzes, tests, or class projects. Students can also register to receive texts containing project or assignment details, due dates, quiz & text reminders, resources, class announcements, etc. No personal phone numbers would be displayed within the app, just usernames. Teachers can add and group students based on their class period, allowing for easy group texts of vital class-related information. Parents can register to receive a copy of all texts sent and received, allowing them to stay in the loop.”

Bill Rosado. His app: “Phone Home: Automatic calling/texting a designated number when the phone arrives at a predetermined destination. Great for teenagers or elderly parents!:”

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 800 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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574 Replies to “How to Take Intelligent Career Risk (and Win Mentoring from Reid Hoffman, Chairman of LinkedIn)”

  1. Thank you for the great post on risk! I can tell you as a surgical nurse with an inventive mind (father was awarded for many inventions for IBM, mother’s father was also an inventor) and an entrepreneurial spirit, my job has left me

    highly frustrated. Doing the same job over and over no matter how challenging it may become kills the spirit a little bit at a time.

    I am a problem solver, I discover new ways to accomplish an end. I am also a humanitarian and it disturbs me very much to see the way medical research is conducted. I have a game changing concept that will absolutely change the way research is conducted perhaps even globally. This is a NEW MARKET.

    I have discussed this method with a trusted Harvard trained vascular surgeon who said it was “brilliant” and with a trusted web designer who said: “you would not become a millionaire”, “you would be a billionaire”.

    One problem, I need the expertise of many others to make this happen and I don’t want to waste ANY time getting this done! I would love to tell you what you need to know to determine the value of my statements but that would require a NDA, non-circumvent and non-solicit agreements. But, this is huge!

    I deeply appreciate your thoughtful consideration! Thank you for your time.

    “Our doubts are traitors, and make us lose the good we oft might win, by

    fearing to attempt”. William Shakespeare, 1564-1616

  2. My name is Stetson and I’m an engineer who’s recently had an insatiable appetite for learning about micro businesses and start-ups. My current career isn’t completely satisfying (although I do enjoy what I do) and I am in the early stages of starting an online business in addition to my day job (I plan on having the pieces together in the next 30-60 days). As an engineer, I am familiar with mitigating risk by applying “factors-of-safety” and redundancy into what I design. As I ponder my next move, I think about how I will mitigate my risk in starting a business of my own.

    I calculate that my risks include:

    1. Sinking time and money into something that won’t realize a return

    2. Work my day job and spend all my free time on starting a business

    3. Become so stretched for time that my performance slips and I get fired

    Now, to mitigate these risks I plan on:

    1. Starting light and simple and testing my product before I even fully develop it (possibly) to see if there is an existing demand

    2. Pick something I really like, so that if I do end up investing a significant amount of time it will at least be on something I enjoy and can benefit from

    3. Budget my time wisely and make my current position the priority until it makes sense to shift its importance

    I expect the first few attempts to be a learning experience, but overall I see the risks as being very manageable. Without taking the risks, I won’t ever know if there is a reward.

    Thank you for this post. I greatly enjoyed reading it. Best of luck to everyone.

    Stetson

  3. I thoroughly enjoyed the “How to Take Intelligent Career Risk” blog post and would like to present my story in seeking a “personalized high-impact session” with Ben and Reid. Much of what they wrote echoed what I have told my 25 year old son and 20 year old daughter throughout their lives and during their college education and it has served them well. They are successfully building their own careers and futures as independent creative free-thinking entrepreneurs.

    It has also served me well over the past 60 years. I have always been a self-motivated entrepreneur who takes chances and risks to pursue crazy ideas and creative inspirations. My primary career has been in entertainment and I have made a respectable living as a musician and performer for more than 40 years.

    I have also been my own promoter, bookkeeper, accountant, agent, salesman, secretary and leader of various groups over four decades, as well as a solo performer for both children and seniors. When the Internet became available, I taught myself HTML and set up my own online business to design and host web sites for myself and other business clients. I am also taking online courses to further my programming and coding skills.

    I have written music and songs, I have developed a premise for a book on seniors and aging, and have ideas and have built web sites for business web applications, mobile apps and web-based e-commerce solutions.

    If I was 30 years old and had a college degree, I’m confident my future would be bright indeed. At 60 years of age, I’m finding that doors do not open, many opportunities are not available to me, and people I would like to work with are not really interested in what I have to offer. That’s understandable and I work around these limitations as much as possible – I’m sure not about to quit. I like what I do and besides, I don’t have a pension or retirement plan that will allow me stop working, even if I wanted to.

    It has been and continues to be a challenging, interesting and satisfying lifestyle with few regrets. I wouldn’t change much, and living a creative, inventive, and unique life has been its own reward. But such a lifestyle is a gamble, as well. You hope and presume that following your own muse and working hard to build your career and fulfill your own dreams will lead you a satisfying life and eventual financial security. Business and motivational bloggers and authors have a great message and strategy for people starting out who are building their careers into the future. But there is also a real possibility that 30-40 years later those entrepreneurial dreams will not be fully realized and the future can look uncertain and frightening indeed.

    So how does a sixty year old entrepreneur apply the ideas expressed in “How to Take Intelligent Career Risk” to life in his later years? My health is good, my mind is clear, my ideas are bold and my intention is strong. But in spite of my hard work, continued efforts and determination, I am somewhat at a loss as to how I should proceed from here.

  4. I’m a mom with two young kids, and I’ve been bringing home most of the bacon for a couple years. Soon I’ll be escaping the “golden handcuffs” of a secure federal government job and becoming a full-time entrepreneur (or ‘dream catcher’)! Sounds risky, and it is, but I’m choosing to leave anyway. But it’s much less risky than staying for job security.

    Why? There are two main reasons:

    – Fulfill my childhood dream and send the right message to my kids. Some see kids as liabilities. They’re not. They are accountability partners, and reasons to find opportunities. They are little people with big dreams who need to see adult role models who are making their own childhood dreams come true. I need to fully become this person for them, and for the six-year old in me who’s still yearning to see her dreams take flight.

    – Take the leap and become who I am meant to be. Some people find fulfillment in the same job/career that they find security. Lucky them! But for me, right now, it’s a choice. Choosing my current job security would have meant missing a huge opportunity. I need to fulfill my future – the one in my childhood dreams – as a gift to the adult version of me who yearns to take her place as an innovative artist, entrepreneur, and creative leader. To me, it’s much riskier to be complacent and become what feels like the wrong version of me. Instead, it’s a lower lifetime risk to embrace my dreams, grow to the next level, and meet the person I am meant to become. I’m choosing the freedom to be myself, on my terms, and on my turf.

    To me, intelligent career risk is knowing that each step of my career path is getting me closer to who I truly am and sharing that with the world. Taking this leap – my next intelligent risk – motivates me and I hope this move will continue to inspire my kids, peers, community, and anyone ignoring that little voice of the six-year-old inside. I can’t wait to be inspired back, by all those who also choose to pluck their dreams out of the dreamworld to plant them firmly into their life.

  5. This is not my favourite post – because it rings too true. I am angry. (To be clear, this didn’t inspire it – been a while building and accepting now – but the timing’s just right. Cheers.)

    My generation was raised in a world with rules that are no longer applicable and ideas that are mostly archaic.  I’d like to take this moment to say: “eff you, economy”.  Yes, it’s easy to be angry, and hell, I still am, but once we get over that and look from other side… it does force evolution.  (Or mutation when I don’t approve.)  We are dinosaurs again – even those that have been given the best there is, the tyrannosaurus so to speak – can’t stand up against the proverbial asteroid. Very “Brave New World”.

    What we were told is the right way to survive is obsolete.  Well.  Isn’t that a brain fuck?  It’s no longer “be prime minister/president”, it’s simply “be SOMETHING”. Heck, even before we get that far, “DO something”,

    My own story isn’t new: creative from the beginning my aspirations where similarly inclined (once it was determined, no, I can not grow up to be a flying polar bear). Well-intended loved ones constantly advised me “No, don’t do X, it’s not a stable future, do like Y instead”. If I had time to waste I’d be angrier at myself for listening – over and over, so many paths not taken – but instead gotta focus on the productive. Anyway, that’s how I ended up compromising (ew) my dreams, ending up with an advanced advertising degree, 3.9 GPA and, like many of my peers, dismal prospects. Two years out from graduation and everywhere I look wasted (incredible) talent is a dime-a-dozen – on a *good* day. And I’m sick of seeing it, sick of playing by the old rules; when the world is making it very clear it’s changing fast and either we take the risk to adapt and thrive, or stagnate and die (proverbially).

    So fuck the word “No”, give me risk, give me fear. We’ve all heard “life’s a bitch” well I am actively choosing to make it mine. To that end expanded my skill set to incorporate my passions and seeing ways to augment my future through them. Because as we know, life without passion is just work, and just work is no life.

    All the best,

    Cole

    Graphic Designer / Illustrator / Story Crafter / Personal Trainer / Freelance Adventurer / Actress / Cook / Really-Just-Kinda-Sublime-Jane-of-All-Trades / Human

    Random Trivia: I was actually drafting this for my next blog post but this is better (I try to keep my blog light/entertaining, if only to myself, so thanks for that).

  6. The change Stanley Lee and I are making is to design a tool that will benefit the LinkedIn community. We are volunteering on this project to learn from each other, to stand out from the crowd and, in the next 60 days, to move us further along a career path and help others.

    In the past five years I, John Pennant, haven’t taken career intelligent risks, I have taken the safest option. This decision has been partly because of having a young family, my own perceptions and seeing a few people who discouraged a career change. This is classic ‘low volatility stability’ which turned out, as you illustrate, to be no stability whatsoever. I am working on Plan Z.

    Up until the college bubble burst Stanley like other recent graduates, believed that they could continue flipping marketable degrees in exchange for well-paying jobs. He didn’t question the real risks and payoffs with this decision until the recession arrived. He’s working on Plan A while pursuing Plan B.

    We are creating a career path tool called MentriCity inspired by “The Start Up of You” that will enhance LinkedIn and will include features that:

    • visualize Plan A, B and Z

    • integrate personal networks with Plan A, B and Z

    • highlight Ben and Reid’s motivational messages

    • enable crowd-source ideas within your network

    • support analytical techniques to help you critically evaluate your Plan A B Z and incorporate intelligent career risks.

    In two months, we will demo the tool and how it works. We will give back to you and the LinkedIn community the end product/solution with your permission.

    Thank you for what you’ve given us with your book and for facilitating our introduction through the LinkedIn discussion group “The Start Up of You”. We look forward to sharing with you our great demo.

  7. Hey ya’ll, my name is Dana – noncustodial mom, single mom, photographer, designer, fundraiser and owner of a crazy, seriously unexpected life – all great things in their own right.

    I believe there comes a point in one’s life where you just know what you’re supposed to do, something that you’ve been created for, something that life has been developing within you, something that each mountain top and valley low was specifically purposed to teach you, and you alone. Each of us lays claim to a very specific purpose. The trick, however, is finding that purpose, believing in that purpose and then dedicating your life to fulfilling that purpose. Not easy, simply because that purpose won’t be handed to you graciously on a silver platter and definitely won’t be free. The vision itself may be free, but the way you earn it won’t be.

    What change do you want to make in your career in the next 30-60 days?

    Shoo. I’m the queen of over-thinking, over-thinking so much that I’ve amassed an insane amount of distractions in my life. No distractions as in things or people, but distractions as in allowing my constantly creative mind the freedom to throw curve balls daily. A creative mind can be an amazing thing, yes, but only so much so if you know how to control it and tell it where to create. And knowing the boundaries of where to create and where to spend precious mind hours comes only with years of making wrong decisions and/or making no decisions at all.

    So the change I’m making and the risk I’m taking is to remove all distractions and focus on what I know I have to do. Instead of running in multiple directions making little to no headway and living in constant frustration and confusion, my focus has now shifted to ruling my life’s work – changing up the traditional portrait fundraiser by offering extreme levels of cash profits – to the tune of $26k+, for free. Fundraising needs a fresh face, a free face, a face that offers 100% cash with a “no questions asked, no money down, no money ever” guarantee. We need to bring life and hope back into our communities, giving them the financial freedom to dream, dream big and function effectively and efficiently. Most communities are stunted because they are ill-funded or sadly running in the red – that’s no American Dream!

    We’re here to change that. Our motto: “You Dream. We Fund. For Free.” says it all.

    How do I think about the risk involved in this move?

    Let me put it this way. Married at 19, divorced at 27, lost custody of my two older boys to a tyrannical ex, now 7 years ago; got pregnant – became an instant single mom in the split second it took me to tell him I was pregnant; gave birth to a 13.2 pounder, unassisted, by choice (talk about empowering); lived in a homeless shelter for 8 weeks, with my 2yo; lived in a hotel for 9 more months after that; slept in my car countless nights, wherever we could hide. We’ve lived in KY, OH, TX, FL and TN – all within the last three years, just trying to find our way. I’ve been unemployed and severely underemployed. I’ve traveled the country twice, with my 2yo, camping in our car, at primitive beaches in Texas, dense forests of Arkansas, truck stops and WM parking lots across the way, just wherever really. I drive a car that has 211k miles on it, windows don’t work, air barely works, tires fading – again, but it securely carries all we own and it’s paid off. I’m single by choice – have been for the last 4 years, and we live without “things” so I can stay off government assistance.

    If I can survive all that hell and the risks and daily challenges involved with each, I’m pretty dang positive I can survive another risk. When you’re used to being shot at from every angle it becomes sort of a game to see how quick the bullet can be dodged or, if shot, how creative one can be throughout the healing process. You learn to suck it up, smile and go on.

    So what I think about the risk isn’t anything compared to the way I take that risk and transform it into an opportunity to grow and push me further outside of my comfort zone – where my vision is waiting with open arms. Besides, “it’s my life, it’s now or never; I ain’t gonna live forever…”

  8. Business, as life, is simple. We humans just make it complicated.

    Risk is completely subjective. And beyond certain inherent human, evolutionary tendencies, we as individuals decide what we consider to be risky or not…within our own, self created realm of perception (the glasses we see the world through).

    So in following with this belief, excellence (not success…key difference) boils down to 3 things:

    1. Dont chase success…chase excellence. Success will follow.

    2. Don’t search for opportunities (too limiting and reaction based)…rather, position yourself (mentally, physically, emotionally) to ATTRACT opportunity, know how to recognize it, be prepared when it surfaces, and capitalize.

    3. The number one key to achieving something great: a crystal clear vision, combined with unrelenting persistence. Ingrain this mentality.

    It’s that simple. I’ve seen it work my entire life.

    Thank you sincerely for the opportunity.

  9. My goal in the next 30 – 60 days is to launch a product based on an idea I have spent the last 1,095 days working on and yet much to my agony is still mostly just a graphite scribble in a notebook.

    From the outside it might seem like there is no risk for someone like me who is young, single, has the full support of friends and family, is working a decent paying corporate job I actually enjoy, and has already established a track record of making “risky” decisions throughout his life like-

    1) Leaving an engineering degree behind the day I graduated from college to instead pursue product design at a tiny, no-name five person start-up only to end up stuck designing those horrible cut-your-finger-every-time plastic blister packages.

    2) Continuing to travel alone internationally even after being conned, robbed, and mugged over the years; left with no passport, no drivers license, no credit cards, and not even a penny of cash on me in a third world country.

    3) And/or uprooting my entire life and support network in California, moving to NYC (a city I’ve never even liked, let alone had even a remote desire to live in), and living in a run-down government housing project with a 50 year-old Puerto Rican lady and her 5 dogs in order to stretch my savings long enough (while working unpaid internships) till I could find the specific position I wanted with one of only two companies I wanted to work for, during possibly the worst global economy I’ll ever experience in my lifetime.

    While these may sound like risky choices to some, for me they were no-brainers. I considered them wonderful learning opportunities and growth opportunities, which I can proudly say have made me a better person in every way possible. So if I don’t think of risks in terms of physical, financial, or identity-based threats, what DO I think of risks in terms of? Well, there is one very real risk that I think about whenever I’m faced with a tough decision. It’s a risk that’s always in the back of my mind asking, “Is this really going to be worth it?” That risk, is the risk of regret. I don’t mean the self-defeating kind of regret that some people use to dwell on the past as a scapegoat for present unhappiness, but rather the kind that makes your soul ache because you so badly know what you want, you know you have the ability to get it, you’re willing to give up everything for it, and yet somehow, it still manages to feel like it’s slipping away.

    “Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” -Mark Twain

  10. Thank you Tim Ferriss, Ben Casnocha and Reid Hoffman for this helpful post.

    I spent my last few days thinking hard about my risks, what opportunities I’ve missed, my directions, and my plan to change.

    1. I am Nhat Le.

    A young Vietnamese who has

    • 20 days left on his grace period

    • Limited U.S. networking. (his HUGE mistake)

    • very little financial resources ( but he know that he’s still a lot luckier than many people)

    • a dream to have a successful business/marketing career & to be an entrepreneur.

    I came to the U.S. in 2011 to finish my senior year in Economics. (My university has a 3+1 program with Colorado State University). At first, I planned to go back to work in Vietnam, and I stuck to that plan until last Friday, June 15th.

    The biggest risk and opportunity I’m about to miss is the U.S.

    2. In the next 30 days I want to

    • STAY! And make my own American Dream. The post really helped me to visualize who I will be, and whether I want to be a man with flexibility.

    • Stick with my business and marketing path. Firstly because of the original reason: my country is poor. For me, I want to be a successful entrepreneur, creating more jobs and more hope for Vietnamese youth. I want to learn the entrepreneurial spirit and inspire others. The best place to do that is here, in the U.S., and right now. The second reason: this post tells me that I can be stronger personally & professionally in the long run.

    • Be better at networking in the U.S. In Vietnam, normally we don’t have such straightforward networking with strangers. I attended all the workshops and events available in my U.S. university last year to learn networking. Networking is still not natural for me, and I want to improve.

    3.How

    • Maintaining my status so I could legally stay & look for opportunities in the US.

    • Finding ways to make money. My family can’t send me more.

    • Looking for opportunities: online & networking. Volunteer & Internship.

    • Emailing people. It’s the most practical way for me to start now.

    4. Worst things can happen:

    No jobs and/or no money so that I have to go home. Most of the time, companies only sponsor international students with specialized technical skills. In addition, in this economic situation, although I have the aspiration and the assets-my skills to start, but the reality is hard.

    If I have to come back to Vietnam, of course I can apply for a grad school to come back. Of course I can get a decent job in Vietnam. The important thing is that I don’t want to be in that scenario. Just like the “4 hour work week” (I read this book in Vietnamese 2 years ago), I don’t want to be a fat man in his red car, I don’t want to be “so so”. I try my best to stay with my adventure now.

    5. So for the last few days, I:

    • Applied for OPT to extend my stay. I can be denied. If I am unemployed for too long, I will be asked to leave. And I spent 380 out of my available resources. But now I’m thinking of this as a trade-off for a much greater opportunity.

    • Reached out. I’ve been talking to a lot of people, starting with my friends, and my closest leads first. They provided me with useful feedbacks, and I get more sense of the road ahead. (So this is the 3rd mistake: underestimating available resources)

    • Applied for several jobs & Expanded my search to part-time & internships. Not much hope so far, but I will try harder.

    It amazed me that if I avoid the risk-the fear, then it will always be uncertainty. After trying to get myself used to the sense of lost, I actually, only just barely, get a sense of directions (and hope).

    (Just to say wow, because there are so many great stories. The first time I read this post , there were only 16 responses. Now there are over 400!)

    I’m telling my story not only because of the prize, but also because I want to let you know that the post is really meaningful for me, that I thought hard about it and that I’m changing.

    Again, thank you!

    Nhat Le.

  11. Thank you Tim again for another inspiring post, and thank you Reid and Ben for taking the time to participate in this.

    I am 27 years old and six months ago I was let go from my job as an institutional equity trader on an equity trading desk in Toronto. It was a position that I had become comfortable in, paid well, but I was no longer challenged on a daily basis and often bored. Needless to say, I had been unhappy in the seat for quite some time and often had feelings of guilt that I was wasting my life because I wasn’t getting to do and see all that I aspired to in life. It took about two days sitting like a zombie on my couch for the the initial shock of unemployment to wear off, but then I realized I had been given a special opportunity to take the time to figure out what it is I really want out of life, and determine how to accomplish that. I had been in the business nearly five years and made some good relationships so I think had I wanted to get back into it, I would have been able to, but every part of me was telling me that wasn’t the right thing to do. I have always wanted to travel, and to live in other cities and that was what I decided to focus on doing. I needed to get back in touch with myself, and find my inspiration, because these things seemed to have drained away after years of sitting in a corporate seat.

    I had modelled a bit in university so I contacted my old agent, who I had stayed in touch with, and talked to her about what sort of opportunities there were for me to work and travel. It wasn’t going to be easy, in the fashion world I am old, but otherwise still fit the criteria so we decided to give it a try. I moved back to my parent’s house in the suburbs, from my apartment in central Toronto, and worked for over five months in Toronto building up my portfolio, and getting paid pretty much nothing. We reached out to agencies across the globe and kept getting told no because of my age. Rather than giving up, I decided to get on a plane to London and go round to every single agency if that is was it took. Luckily I didn’t have to go to every agency in London, but I did get an awful lot of no’s before I found one who said yes. I have been in London for two weeks now and couldn’t be happier. I know in my heart that this is where I am meant to be, but now I need to figure out a way to financially support myself to stay here longer. I have thus far been living off my savings as it still can take some time before you start making money in a new market so its hard to gage if this is sustainable.

    But this is also not what I want to do for the rest of my life, it is more an interim fix to hopefully support me while I sort out the bigger “whats next.” I have always wanted to start a small line of women’s clothing, an idea that came to me out of the struggles that I had looking for practical but nice clothes for work and I have another idea for a type of women’s undershirt that I think is missing from the market. However, I have no idea on where to start for either. So I found a short course offered at the University of Arts London that is geared directly to what I want to do and signed up for the July session. This is another expense for my savings account, but I know it will be worth it to get some direction and to get the ball rolling. It is always the first step that is the hardest and even harder when you have no idea where to put down your foot.

    In the meantime I am also reading the book recommended by Tim on this blog, App Empire, and am brainstorming app ideas that I could get started on and that could be a potential source of cash flow while I get my other dreams going. I am also writing daily about my experiences and hope one day to write a book about how I made a turn in my career, and life, to go after what I really wanted rather than settling back into a job just for the money.

    The risks I worry about are the fact that I am draining my savings account and I sometimes have moments of weakness when I think it would be so much easier to just go back to finance. To get over this I just remember how unhappy I was at work and how much I am enjoying the freedom, not just of my time but of my mind as well. And when I tell people what I am doing, and what I used to do I often gets looks like I am crazy, but I just ignore those and keep moving forward. Lastly, when I am told no I don’t let it settle on my conscience, I blow it off and keep moving forward looking for the next possible opportunity. All of this is very scary, I have never taken a blind leap of faith before, but I am surviving so far and don’t want to give up especially since I feel like this new journey is just beginning.

    Thank you for taking the time to read this.

    Michelle

  12. Where I Want to Be:

    I want to lead a global movement which will inspire women around the world to take control of their personal finances.

    Where I Am Now:

    I am currently in my third month as a Product Designer for a global architecture firm. Although I enjoy tinkering with the app’s designs, I find myself continuously being drawn towards talking to our users and developing use cases. Fortunately because we are a global company I have the opportunity to communicate with people around the world. What I have found however is that video chatting in no way replaces the feedback that can be gained once trust is built in a face-to-face conversation. I am stuck within my job because I want to continue to help our design team understand our users but am limited by the distance.

    Where Do I Go From Here:

    I realize that the jump from my position as a designer to leading a movement around finances is rather large, but from where I stand there seem to be small leaps of faith which I hope will lead in the right direction.

    >>The first leap I see – convincing my manager to allow me to travel to our offices around the world in order practice my interviewing and communication skills with people of various cultural backgrounds.

    >>The risk – Six months ago I left my job in Los Angeles at a non-profit (where all of my actual past experience is in) for an internship with the firm’s global support team so that I could move back home and save money. It was within that internship I realized I had an interest in design and was able to magically land my current position. With only three months of experience in design and only six months experience at the company it is quite a stretch to convince them to send me around the world in order to help them better develop use cases. Will this request be too aggressive? This is the fear I hope you can help me overcome as I prepare to make this leap!

    Thank you for the inspiration,

    Kat

  13. On the cusp of launching my first company and after half a year of working with another start up here in Japan, I’m about to take another (final?) jump out of teaching–the way I’ve been making a living for the better part of the last six years–this timely post sent me on an unexpected introspective journey on this next phase as well as the path that has led me to adopt similar ideas on risk as those in this post.

    My dad always tells me I must like choosing the difficult way to live. I always thought I just liked choosing the interesting way, but looking back over this last decade of my life, I can see his point.

    It started by changing majors from engineering (set career) to anthropology (who the hell knows). What seemed like a huge decision then, I realized my first big lesson. It’s better to follow something you enjoy in the pursuit of self growth than choose something just because it feels safe.

    I took that to mean I should then move to Japan and study the language. I got a teaching job at a school and loved the life and the feeling of being alert to every second of every day, the way only living in a foreign place can (I had been traveling since age 15, so I was addicted to this fact early on). After six months, the school offered me another year, but I turned it down. I thought I had already gotten everything I could out of the job. But I had not gotten everything I could out of Japan (and maybe still haven’t).

    So I decided to stay another year, but tried to make my own way as a private tutor. This was much harder said than done as I didn’t know how to build a clientele. My wake up call came a few months in when I only had $30 left in my bank account. I realized that I was about to be in serious trouble, but I also realized another important lesson from taking a risk. Urgency leads to action, and hitting rock bottom was kind of a rush (not that I’d like to stay there).

    I saved up enough money to move back to the US a year later, only to move from my home in Texas across the country to DC with my dog and very little cash. It was another chance to try a completely different environment and hopefully learn more about what I wanted to do. I rented an overpriced basement, and got a job at a small luxury real estate company. I was hired to do marketing and work under the VP of Operations. When the VP walked out on the company one day a few months in, I was the only one who knew enough about running the company. So I got to take on a whole lot more. While everyday was hell, I learned the equivalent of an MBA in a few months. I knew that was valuable, but I also discovered something: responsibility and decision making was not as scary as I had always made it out to be.

    But I set out again to Japan to follow my heart, be somewhere I wanted to be, and pursue designing my life to be like how I wanted (this was the moment I discovered 4HWW). I spent the next two years learning more, and trying to act on spur of the moment ideas before thinking had a chance to interrupt.

    Now, I’m excited to leave yet another rut that I’ve made and set out on something I feel like I’m made for. I don’t know the best way to do it, but whatever happens will be yet another amazing learning experience. Hey, if everything goes completely south, at least I have some rice fields, supportive friends, and family.

    1. Hey Nate,

      Sounds like a similar path that I’ve taken. I too spent some time in Japan (and other parts of Asia). Loving anthropology, yet deciding on going the diplomatic/ political route, I began to dig myself in a rut. I then came back to Chicago and started on a new path of entertainment, music and acting. That went good for about a year and a half, until I began to get turned off by the industry and decided I had to follow my heart more. So I went back to Asia, for a diplomatic delegation in Beijing. Spending a week in North Korea and wanting to take action with the refugee crisis there, I proposed a solution at the Ministry of Foreign Affairs in Beijing. No luck there it turned out (because those politicians are hard to persuade with their thick heads), and so I returned back once again to Chicago. So I feel ya – i know how the risk and rut life can be.

      Just curious, when you say on the cusp of launching your first company, are you talking about something teaching-related, or is this a new risk you’re about to take on? cheers man !

  14. Hi Ben, Reid and Tim

    I’m Rachel. Previously I was a Chartered Accountant in roles of Chief Financial Officer and the likes with a life that the employer owned and I had no control over. In fact I felt I wasn’t able to get ahead because people got promoted for “being seen” at the office with the most incredible hours and not results. There’s always someone who’ll stay longer.

    In any case after investing years on this career path I knew it was not my dream come true. It was a prison sentence for the rest of my working life until my employer said goodbye or I fell over.

    In 2008 I said enough is enough and I went on a 3 month overseas trip exploring Egypt, UK and Europe with my husband and two girls. What an awesome experience. I decided it was not going to be a once in a lifetime trip but something I’d make sure I did regularly. When I came back I knew I had to reinvent myself.

    Initially I did accounting consulting in a role that was flexible with bouts off in between work where I could develop my plans.

    I chose to trade financial markets because the rewards are not based on an hours for dollars formula. A lot can be automated. It is an area that I love and find challenging so really enjoy the time spent doing it. You can also be geographically free which is exactly what I want.

    Since late 2009 I’ve dedicated all my time to trading my own account. I have had to evolve into a different person to trade the financial markets. I’ve had all sorts of obstacles and pushed through them. Falling over and picking myself back up. In this journey I’ve become someone else. I had to learn how to become a risk taker, stay calm in chaos, embrace uncertainty and take control over my time and priorities without someone else telling me what they are. Because the transformation needed was so great, at times I have hated it but kept going holding onto my dream of how different the future can be.

    Now that I’ve transformed myself into someone new and have expertise in this new industry I need to take hold of many of the opportunities available to anyone who dares to grab them. I have a brief business plan that I’m getting started with right now and some of the paths I’m going down are seemingly outrageous to me but so exciting. Among other things I need online global networking opportunities to turn my ideas into reality and launch my brand and get exposure. From there I can take action and create the exciting opportunities I seek.

    I’m reading “The 4-Hour Work Week” and it has been the encouragement I need. Some of my ideas would seem really outrageous to others and I’m hesitant to discuss them fully with family and friends because there will be a lot of reasons suggested as to why it won’t work out. I fully agree with Tim Ferriss that there is little competition when you think outside the box (unrealistic) and dare to do what no one else will.

    I’ve done the ground work to reinvent myself and now it’s time to make the journey worthwhile.

    This mentoring opportunity to work with Ben and Reid would be life changing for me. It would directly help that which I seek to achieve. I have come from a family background that knows nothing but working as employees. I’m going to break out of that way of life and be an inspiration for my children and others. Your help and guidance would be invaluable to me. This is not a flimsy wish with me, it’s a big commitment that I’ve made and am making and I’m going to succeed no matter what. If you join me on this journey I’ll be eternally grateful.

    What change do you want to make in your career in the next 30-60 days?

    My full plans will take longer than this to implement. However, in the next 30-60 days I will be launching my brand online and gaining exposure as an expert in the field whilst taking advantage of global networking opportunities. I have specific strategies to help me achieve this and your advice and contact would greatly improve this. All my further business activities follow on from this first step.

    How are you thinking about the risk involved in this move?

    In recent years I have transformed myself to embrace risk where the reward is worthwhile. I get up in the morning excited about the future knowing I’m taking action to make my dreams a reality. I make my plans and then take one step at a time without over-thinking it so that I don’t freak out or feel overwhelmed by it all.

  15. Gentlemen,

    Firstly, thanks for serving up these insights into biases against risk – I guess we’re not all so far removed from knuckle-dragging as we’d care to think – helps put some context on my own chequered employment history, including the current physocally demanding night-shift one!

    Trickier to note the power of risk-averse significant others.

    However, to paraphrase Groucho Marx, “I wouldn’t want to belong to a club that would have me as a member!” For me, switch out “employment” + “employee” for “club” + “member”.

    Your piece adds force to my current plan over the next 90 days (OK, let’s make it 30-60) – having noted the, possibly never greater, opportunities and resources available (think – crowd-funding; own network’s support; marketing needs of start-ups, not-for-profits, established businesses) – I’m saying “Yes” to voluntarily supporting same locally, journaling best practices (from a solid marketing framework), and crowd-funding the results, to monetise future consults and information products.

    Also saying “Yes” to: further reflection on risk aversion, and worst-case analyses; writing opportunities; and possible future rejections (a la this – heh, heh).

    Your advice re: any/all above would be most graciously received.

    Also: kudos/thumbs-up to Tim – previous posts of yours kick-started my lucid dreaming, and T.I. swimming. MAK

  16. Ben and Reid,

    First and foremost this was a great article and gave me a new perspective on how to look at “risk” in everyday decision making. My story is a little long-winded but please bear with me as I will keep it short. I’ve been in the health care field now for almost 5 years and in entering into my profession took a job with low pay position but highly profitable in the life-learning department. Long hours, weekly public speaking encounters, high patient volume and daily debriefings on how to handle certain office scenarios left me exhausted and sick to my stomach at the time but, looking back at it, these experiences having helped me tremendously in current every day life. I am currently at a different job but in the same profession as we moved to a different state 3 years ago. For the past year I have started to constantly wonder if there is something else out there that I am suppose to be doing. I try to stay focused and up to date on my current profession but find myself drifting further away from it. To add a little spice to the matter, my wife and I are expecting our first child in the beginning of Autumn and in a year we will be relocating 550 miles away from our current location.

    With the changes in family structure and relocation on the horizon, this gives me a chance to explore other career paths but I still have bills to pay and need to continue to bank income for the new addition coming soon. I know that everything will be status-quo if I just “suck it up” and stay at my current job but what I’m really looking to do in the next 30-60 days is make a plan that starts with a likely career change that would transfer to our future place of residence. I’m looking for an opportunity to help me in creating a business that leaves me with personal satisfaction and in 5 years being able to tell people that job success starts at “doing what makes you happy.”

    Honestly, the risk involved in this scares me. We live comfortably at the moment but I still feel that I’m not happy with what I do. I’m trying to determine if my plans should wait until we move in 1.5 years along with deciding if the risk at this point of changing my career is worth it. I feel like if I wait until we move to make the change that I am wasting valuable time.

    Thanks for the opportunity,

    Joe

  17. Gentlemen,

    Firstly, thanks for serving up these insights into biases against risk – I guess we’re not all so far removed from knuckle-dragging as we’d care to think – helps put some context on my own chequered employment history, including the current physically demanding night-shift one!

    Trickier to note, however, the power of risk-averse significant others.

    However, to paraphrase Groucho Marx, “I wouldn’t want to belong to a club that would have me as a member!” For me, switch out “employment” + “employee” for “club” + “member”.

    Your piece adds force to my current plan over the next 90 days (OK, let’s make it 30-60) – having noted the, possibly never greater, opportunities and resources available (think – crowd-funding; own network’s support; marketing needs of start-ups, not-for-profits, established businesses).

    I’m saying “Yes” to voluntarily supporting same locally, journaling best practices (from a solid marketing framework), and crowd-funding the results, to monetise future consults and information products.

    Also saying “Yes” to: further reflection on risk aversion, and worst-case analyses; writing opportunities; and possible future rejections (a la this – heh, heh).

    Your advice re: any/all above would be most graciously received.

    Also: kudos/thumbs-up to Tim – previous posts of yours kick-started my lucid dreaming, and T.I. swimming. MAK

  18. Phenomenal I’ve literally found this post at a stage where I am increasing risk ten fold!

    I graduated University with a Law degree in a climate where lawyers where being struck off and training contract places where drying up!

    I offerred my services for free to numerous firms for a year and the outcome was… I discovered I didn’t like Law!

    So I took a job with a multinational Clinical Services company, became an expert in my field for the company but now I want more!

    I’m training myself in web design, and am starting a business where I can share my knowledge. I have enrolled in an MBA, taking a day per week out of my working life to get more education, not to mention the risk of the expense.

    I firmly believe that it is not the events in our lives that shape who we are but how we perceive them.

    I will be a succes, I will run a multi national some day. The ethos of constant education will create the leaders of the future.

    This opportunity would accelerate my progress and in return, I would give my all.

    The moon is only far away for me because I don’t yet know how to get there.

    Niall

  19. I’m a 32 year old, father of 2, currently employed in a fortune 500 company and will soon be finishing a 2 year leadership development program focusing on six sigma and lean methodologies. The company plan is to then “re-integrate” me into the business to help run and grow the business.

    I have also been a “wantrepreneur” ever since reading the original 4HWW, but have recently started to put some more serious thought and planning into either product ideas, retail websites, and a financial planning process.

    My decision and the risk I’m balancing is between moving into a corporate role, that I will need to be fully committed to; both to succeed and to feel that I’ve succeeded, or to start my muse and enter the unknowns of small business. I am a quick learner, a critical thinker but I freeze at times when I’m unsure of how good/poor the end work product will be and end up not executing as fast as I should.

    To me the safe route is to go into a familiar role within my company, I will be good at it, I will get my 5 to 8% raise and go on with my life. The next level of risk is to move into a role that I’m not familiar with, but with my base skills I would probably do well at. After that it’s to start my muse, while working and run the risk of being asked to leave my company if they find out.

    Thanks for the post guys, even if I don’t win the act of writing this comment has actually started to help focus my thoughts around next steps.

    Cheers,

    Wade

  20. I’ve already submitted my response and I’ve been reading many of the others, it’s been really motivating and I think we need to find a way to harness the incredible energy and enthusiasm shown so that we can keep up the momentum or encourage/help eachother in the future.

    It seems we all have a lot in common, it would be a shame to let the opportunity pass, I hope I’m not alone in this……… any ideas?

    1. Jonathan, I feel ya.

      Those who find interest in other’s post should exchange contacts, whether that’d be email, facebook, twitter, whatever..

      Get the networks strengthened and evolve.

      1. Great idea and I can also recommend “The Start of You” Discussion group on Linked In.

      2. Cheers guys,

        @John Pennant I’ve joined The Startup of You group on Linkedin. Looks interesting.

        If anyone wants to connect add me on Linkedin: Jonathan Lamptey.

        It would be great to stay in touch

        best

        J

  21. Thank you for the great post

    Few months ago I quit my job of over 11 years to move to another country half way around the world to start a start-up focused on a domain I was not familiar with. However the opportunity it presented to learn and be part of all aspects of building a product was immense. Starting a new venture and moving at the same time had its challenges as it involved dealing on both family and professional end on getting everything lined up. Even after 8 months ride is still pretty turbulent.

    However as the initial pace and frantic activity dies down, for the start-up I am looking in the next couple of months to get myself in to marketing since that’s one area where I don’t have past experience. I believe it is one of the important areas to master to get your product known, get users engaged and iterate to improve your product.

    Since this is going to be just one of the few other things I am going to be doing at the same time, it carries the risk that I may not approach it in a manner that is expected or commonly followed. May lead to false starts and as a result loss of time and added expenses.

    However in my mind I am thinking, risk creates opportunity.

    I may end up talking to a potential partner, investor or get to identify the need of the market in my area more clearly. Any of these would be worth the effort put into it as it allows me to set a foundation from where I can further build and grow.

    Rahul

  22. Roll the clock back 20yrs, a teenage girl is graduating high school in England. No one in her family has ever been to college. Does she even bother to apply…to Oxford? The time, the effort, the cost? Wouldn’t it be less risky, to just start work and earn some cash? She goes for it! The moment she says YES, she works on reducing the risk of not getting in..preparing in everyway she can. Does she make it? Maybe, maybe not…but the point is she tried.

    The same girl, 10yrs on, she meets a guy in Beijing. He’s tall, blond and handsome. She’s small, dark and debatable…Does she ask him out? She goes for it! The moment he says YES, she works on reducing the risk that he’ll not like her. Is there a happy ending? Maybe, maybe not…you get the point…

    Well, that ‘Risk-Reducer’ is me. Most of my life, I’ve tried to say YES to risks but because I have a healthy fear of failure, I’ve worked in every way to try to reduce the ‘risk’ of the worst case scenario. Your article has helped me reflect on all those risks I’ve unknowingly taken and now realise that almost every one of those has turned out FANTASTIC! That in itself is worth a huge THANK YOU!

    I am right now at a turning point for another ‘RISK’ and would love for your assistance in helping me REDUCE that risk! I am that risky ‘mid-flight in a career who’s pivoting into a new industry and feeling re-energised by the challenges’ that you talk about – I hope you will see the associated opportunities! I would like to start an online travel planning site for families. I have a great idea but no experience in the tech/online field (I come from a corporate background) – but am absolutely hungry to learn and willing to go for it!!

    So in the melodic words of ABBA – ‘Take a Chance on Me!’

  23. It´s funny, I consider myself risk adverse but there are times when you have to be honest with yourself.

    Often the perceived risk is like you´ve been edged out onto a branch and you´re better off jumping in the water then trying to hold on until the bough breaks.

    I remember being offered my dream job: assistant stylist at a busy photo studio. I had worked there for a week or two, things went well enough and they offered me the job. I was so thrilled but then they told me the salary. I wasn´t angry; I was crestfallen. It was so low that I wouldn´t be able to pay my rent, or do my laundry, or use the subway. I told them that I was thrilled but that I would have to get a second job to be able to afford to work at the studio. They protested that they didn´t want me to do that. They admitted that they hadn´t raised the rate in several years but perhaps they could reevalute their offer. There was a bit of back and forth but we settled on a 50% increase on their original offer. I wasn´t playing hardball and probably could´ve gotten more but I felt like it was a smaller risk to turn down a dream job that I couldn´t afford rather than accept a job and possibly loose my apartment.

    Several years later at a party, someone said that I would make a good concierge. I didn´t take it very seriously but my stylist career wasn-t going well. It seemed an enormous risk to abandon my career but I was getting more and more broke by the day. I didn´t know anything about the industry but I agreed to the interview and made a complete shift in my career path.

    Later that year, the hotel was sold and we were all laid off. After making the rounds of interviews I had several offers in front of me. I sat down to lunch with several friends at a men´s club for fly-fisherman. I detailed the three dominant offers.

    1) A brand-new hotel, in the same neighborhood as the previous hotel, roughly the same price-range as the previous hotel, likely a similar clientele as the previous hotel, slightly different responsibilities, and roughly the same amount of money.

    2) A well-known 5-star, 5-diamond, luxury hotel with an impressive international reputation, in a different neighborhood, rooms at nearly 8 x´s the price of the previous hotel, a completely different clientele, similiar responsibilites, and likely a bit more money.

    3) A brand-new building of luxury apartments, in a very different neighborhood, very different clientele, likely more responsibilities, and roughly the same amount of money.

    There were advocates at the table for each of the offers. I felt most comfortable with option 1, or possibly option 3. Option 2 seemed the most risky, the most unknown, in truth the scariest.

    I felt that I had the opportunity to do the same thing I had been doing or to learn something new.

    I was scared but it was my very fear that led me to choose the 2nd option.

    The risk paid off immensely. I was very successful in my job and probably earned 3x´s what I would´ve with any of the other two options.

    I loved the job but it´s incompatable with being a single parent of a 3-year old.

    I´d like to change jobs while maintaining the passion and intensity that made my previous job so engaging.

    I look at risk and changes in a whole new way.

    Trying to make a broken system better is insanely risky.

    Learning something new may not be easy but it´s within my control.

  24. First, some background. I’m a 5th year attorney with a solid real estate/finance background and some corporate experience at a “BigLaw” firm. I consistently receive strong performance evaluations and my clients have expressed satisfaction with my work to my superiors, but my practice area suffered a lot during the market downturn and is only beginning to recover. I will be up for partner in 3-4 years, and while a lot can change in that time, I’ve seen associates with more hours/collections than me ushered out the door instead of being promoted to the partnership. Until such a decision is made, I have a stable, low risk career as an associate. I recognize, however, that not making partner will be an “external shock” that will leave me in a weakened position. I would rather make a move on my own terms rather than having the decision be forced upon me and leaving now gives me the opportunity to grow and broaden my career options by developing skills I won’t have if I stay at my firm. Right now, I see myself with two options – entrepreneurship or another law firm opportunity – with a sliding scale of combinations of the two in between.

    Option 1: Entrepreneurship. Soon after I started practicing law, I found myself trying to come up with something entrepreneurial on the side. One of my primary complaints about BigLaw is is how I often feel that we don’t create anything. Being a service industry, we don’t have something tangible to really point to at the end of the day – no lasting legacy And helping people doesn’t really feel so good when you’ve heard a partner tell you: “At the end of the day, who cares what type of law you do? We help big companies make money and we make a little bit for ourselves.”

    I’ve been spending more and more time thinking up startup ideas in my downtime when not in the office. I’ve seriously considered – at different times – a microbrewery, a tech startup, a real estate development project, and an e-commerce niche business. Each time, my lawyer tendencies kicked in and I overthought the risk, deciding that it was too risky a play to make. While there’s no guarantee that I would have succeeded at any of those, it’s always a bittersweet feeling to watch someone else execute on an idea you had – validation that I was on the right track, but sadness that I didn’t jump in wholeheartedly. This falls in the area of “an opportunity where the risks are highly publicized”. But I’ve begun thinking of ways to manage the downside risk (i.e., continuing to practice law in a lesser capacity; or as described below, learning IP from my father).

    Option 2: Law Firm. One of my very good friends at the firm had a solid book of business here and a great file, but didn’t make partner. A few months ago, he left and joined a litigation firm in town that is expanding into the transactional practice. He’s swamped with the work he brought with him and the clients that this firm has put him in contact with and needs help to grow the business. He’s asked me.

    Short term, it’s a paycut. But this would be a “job that pays less in cash but offers tremendous learning”. I’d gain:

    1) Knowledge: I typically represent banks while my friend represents developers. I’d get to learn a side of the practice I haven’t worked much with before.

    2) Connections: Partners at the firm have a lot of valuable contacts in the area that they want my friend and I to meet.

    3) Experiences: I’d be working to startup a new practice at a law firm, building our own business within a firm, which might satisfy some of my entrepreneurial longings.

    Factors to Consider: I’ve been married for about a year. My wife has her own career in HR to think about, but she’s been considering a change for a while as well. However, she has the opportunity to get some valuable training and certification at the job she has in the next 6-10 months. We own a house with a mortgage and have two dogs. The house can be sold, the dogs can find temporary homes with my mom (who loves them like the grandchildren she doesn’t have yet), but above all, my wife needs to be on board with this decision if we’re going to make it work. She has an adventurous spirit, has always wanted to try a new place to live, and really just wants the two of us to be happy. We’ve discussed all of these options, and she’s just as excited as I am by the possibilities.

    Yesterday, I spoke with my friend about the law firm opportunity. told him that I was concerned about joining his firm only to leave soon after for something more entrepreneurial if such a course would adversely affect him personally within the firm. He told me he has no doubt I’d be able to cover my expenses at the firm, so I won’t hurt him economically, and the hire is his decision alone – the other partners won’t be bothered if I left.

    Analysis: Between joining my friend’s firm and going the entrepreneurial route, there’s a long middle of options combining the two. I could join the new law firm while at the same time continue working on entrepreneurial side-projects. Or I could focus my energies on a startup while simultaneously working with my father (who has his own intellectual property law firm) to gain some valuable IP skills.

    Options closer to the entrepreneurship side, however, give my wife and I the opportunity to try an adventure we’ve always wanted: living abroad for a few months. If I make the decision to go 100% after a startup (whether real estate, tech, or otherwise), we will probably sell the house and try a few months somewhere like South America, teaching English, traveling a bit, and finally getting comfortable with my Spanish (I can read/write, but can’t speak conversationally). Upon our return, we might head for the Bay Area and focus on the tech space or somewhere else in our home state while putting together a real estate development.

    Conclusion: Somewhere in the middle is my likely ending place. I don’t think a law firm practice will ever stop me from craving the independence that my own business might offer and I will always look for a side business to pursue. On the flip side, I will never give up law completely. Learning from my father could be a valuable opportunity, and I don’t see myself ever giving up the pro bono legal work I’ve been doing.

    Today, I spoke with my friend and discussed some of my concerns. I told him that I was concerned about joining his firm only to leave soon after for something more entrepreneurial if such a course would adversely affect him personally within the firm. He told me he has no doubt I’d be able to cover my expenses at the firm, so I won’t hurt him economically, and the hire is his decision alone – the other partners won’t be bothered if I left.

    After our talk, I think I’m leaning toward joining his firm while waiting for my wife to finish some of her training/certification. At the same time, I’ll focus some more energy on my entrepreneurial pursuits and try to apply some of this risk analysis to those options – even if I fail, I’ll still be fine. And if my wife and I want to leave next year for an adventure somewhere, I’ll at least have a few months of connections and learning from the new firm. That being said, there’s a pretty loud voice in the back of my mind telling me to travel and then really focus on the entrepreneurship path. Which is where I hope you will come in.

    I’d certainly love to win the mentorship advice, but I feel as if I’ve gained some valuable insights just from reading the article and going through the thought exercise. If I don’t win, I’d appreciate a simple comment reply – whether from Ben, Reid, Tim, or any of the other commentators who have gone through this weighing in on my analysis. I’ve certainly learned a lot just from reading about some of the other decisions people are facing.

    1. Note: the paragraph regarding the discussion with my friend at the new firm about the effect my potential future departure might have on him (which appears twice in the post) was supposed to be under the “Factors to Consider” portion rather than “Conclusion”.

  25. I have been in staffing for 10yrs and I have seen very little evolution on the negative perception of recruiters and some of the time honored but broken ways of getting a job. I have been incubating an idea and have laid some groundwork to enact a change in my industry. At one point, I had built a team to help with the ground work, and have been met with considerable enthusiasm initially. However, it seems that until I can take it to the next level, people seem to come and go – it has reaffirmed my belief in the old adage “if you want something done to have to do it yourself”. My personal battle with the risk involved/ next step has been – what can I do and what am I willing to risk to make the thing I believe could cause a paradigm shift in my industry a reality? It really has gotten to a point that goes beyond success/ money – I want to see a change in the space I love and want to be a part of it.

    Regards,

    Tommy

  26. Hi , I´m Alejandro from Spain. I´m trying to initiate a start-up. I´m not very familiar with this world but I´m all day in internet looking for information and studing . Fortunately I discover this blog and It would be a bless for me have your help and inspiration. It let me focus and not dealing all day with tons of information and trying to guess what´s relevant or not.

    All of life is uncertainty. All of life is a risk of some kind. We are always facing risk to some degree ( We can die at any moment, in a car accident, any catastrophe…) The issue, then, is not to take or not to take risks.

    So the thing is to take the right risk, for the right reason, for the right objetive, and if it´s posible in the right moment. But we all know there´s never the right moment, because there´s always some issues, some problems or some circumstances that we have to face we don´t know how to deal with them. We convince ourselves that we don´t have the skills, the abilities or the right solution and then we let fear drives us and we postpone to act, waiting for the right moment.

    We have to believe in ourselves. Belief put man on the moon. All the conquests in history were accomplished by people with great faith in themselves and their abilities, facing some times, enormous risks, people like Columbus

    There are two kinds of risks:

    The right risks: the risks you can afford to take and the risks you can´t afford not to take. The cost of failure is very low, while the rewards of success can be very great. Or that one that it´s costly but the reward worth it.

    The wrong risks: the unnecessary risks and the risks you can´t afford to take. The consequences of making a mistake would be too enormous. Don´t risk your life doing stupid things. E.g. Jackass

    There are three main reasons or needs we have to fulfill: to grow, contribute and love.

    The objetive we all try to achieve is Money. Money is some kind like love, if you run after it, it´s hard to catch it, it seems to hide.It implies hard work, and some times frustration and desesperation. But if you focus in contribution, make things easier or improve other lives, it will appear in unexpected way.

    Sometimes we act like machines, with machine minds and machine hearts, fighting for the slavery of Money. But we´re not machines, we´re not programed, we have freedom.

    There are three main assets: Money, energy and time. But money is not a real assets. Money is only a tool we use to give things value. And we always confuse price with value.

    We all were born with two gifts or assets: energy and time. Energy, like money, comes and goes, but time never return. Time is our life. Life is a great adventure, a great experiment. We are souls experimenting a human life.

    We are what we do with our energy and our time. To be and to do are active verbs. They imply action, and action implies risk.

    The only risk that exist in this life is not to take any risk at all.

    Thank you for your inspiration that let us grow and for giving us the tools that let us to contribute as well .

    Love you.

  27. Hello, I’m a recently graduated PhD who has spent the past 8-10 years in the comfortable rut of academia and am currently developing a number of small businesses. As for risk, I recently turned down an extension opportunity for my research fellowship in order to pursue my business ideas full time. This will effectively end my potential in the academic sector. The downside is the loss of steady income and “security”, but the upsides are many – too many to list on this posting. Once I began exploring the vast opportunities available in entrepreneurship, business, and technology I felt like I woke up from a deep sleep of ignorance.

    Now I am faced with skills challenges, a willingness to start at the entry level but no one biting, and a strong desire to do my own thing but still needing a basic level of income to supplement my savings (and pay off those pesky school loans).

    My best idea for a business opportunity bridges the technology gap many university research laboratories face when implementing human subject trials – a) limited IT support; b) shrinking research budgets to employ qualified computer/IT professionals; c) operation islands within departments due to high competition between investigators; d) lack of project management training for research staff; (and more, but I’ll keep this brief).

    There are existing companies that could provide products to this customer base, but as they exist now, they target their services towards business clients and business services. I would like to convert some of their products to target the research community.

    My challenge is – How do you sell a company’s product back to them?

  28. Fourteen years ago, I kissed my 8-months-pregnant wife, and boarded the red-eye special for London. I was going back to university to study aircraft design. First crazy thing I’d done in a long, long time.

    My 4-year-old daughter sadly waved Daddy goodbye, wondering what he was doing.

    Sitting in the back row of the British Airways 747, Daddy was wondering the same thing.

    The terror (and yes, it was terror) was almost something I could reach out and touch.

    Fast-forward several years: The family of now four is long since reunited and settled in England. My career has been rejigged, and I’ve been heavily involved in the design of the A380, the world’s biggest passenger aircraft.

    Was it worth it?

    Well, no.

    It cost a lot. I missed out on the birth of my youngest daughter, which still stings me with regret. It hasn’t paid off financially, not yet. I would bury one family member per year for the first five years, and be absent when they passed. My nonagenarian grandparents were expected. My father – not.

    And, yes.

    I set a goal, and went after it. And did it. I am a different, and much more self-confident individual.

    But I’ve never forgotten the terror in the back of that 747.

    Four years ago, I was bored, and money was getting way too tight. I went freelance. My last day on the job, I had no freelance work to go to. The terror was back.

    Fast-forward again. I wasn’t out of work long. Been flat out, actually. Money’s no longer tight, even with the kids now being expensive teenagers.

    But I’ve plateau’d again.

    Time for another big risk.

    So I’m winding down the per-hour work in favour of starting a business that will cut the income/time link. Mobile apps? 3D printing? Something else? Dunno. I’m taking some time to dream and reflect before launching deadlong.

    The terror’s back.

    And not a moment too soon.

    Because now I know the terror is wedded to fun, growth, and joy.

  29. Thanks to both Ben and Reid for the very interesting post and publishing a book along these lines.

    I imagine many of those who read it will benefit greatly and as I look back over my experiences I must admit that it rings true with how my decisions have interacted with outcomes. Therefore I can validate your approach at least anecdotally.

    I have always had a sense that risk perception by most people was skewed and this has been shown by the aversion to loss outweighing opportunities for gains and this is reflected in conservatism in institutions particularly as they are scaled up. I agree wholeheartedly with your contention that trying to nullify risk increases the probability of systemic risk. This is readily apparent today in the banking system, in government and in the pharmaceutical industry.

    This risk paradox also occurs on a personal scale. I remember that as I left one job developing animal models that had become unsatisfying my colleagues thought I was making a bad decision because I did not have another job lined up. Ten years later those who remained have been let go after not being treated well by the company. Over the corresponding period my career has been varied and satisfying although progressing in fits and starts.

    I was fortunate to have a partner who had a great career opportunity at that time. We have functioned as a tag team following our dreams together while supporting each other and our family as it has grown. During that hiatus I spent nine months with my daughter at home before I found an interesting new job at a vaccine development start-up. Being at home with her was a great experience and it forged a bond that continues to this day. Although when I did return to work in some ways it felt like a vacation because the challenges of childcare can sometimes be overwhelming. I cannot stress enough the importance of finding supportive partner(s) to follow your dreams.

    As an introvert by nature I have pushed myself outside my comfort zone to give presentations in order increase my confidence speaking to groups. I do not believe I will ever be a “slick” or “polished” speaker but I do believe that my authenticity serves me well. An example of a speaking engagement that I undertook was to discuss the plausibility of “Jurassic Park” at a Science Fiction convention. This talk led to me joining a group of computer scientists for their regular discussions of interesting topics. These discussions led to the development by this team of one of the first prediction markets on the Web (Idea Futures/Foresight Exchange). This was definitely a group with a high learning clock speed. Your theme of serendipity also came into play here and I have encountered it time and time again when I take constructive action consequences often intersect in surprising and delightful ways.

    I can wholeheartedly endorse travel as a means to personal growth. I had the opportunity to go to Cuba for almost three months. We were immersed in daily life in Havana where it can be a challenge to find the basics and impossible to find many luxuries for any price. Havana as a city is full of history but even more interesting are the Cuban people. They are resourceful in the face of hardship and many strive for excellence and achieve it in the avenues that are available including music, sports or setting up their own bakery. It was a priceless experience with many lessons about health, happiness, history, perceptions and culture.

    My career path as I mentioned has proceeded in fits and starts. After I left one company I found contract employment through a placement agency which became a full time position. I have moved with my partner so she could pursue opportunities while facing daunting challenges in finding work in my field since biotech activity tends to cluster in hubs. She has likewise moved to support advancement in my career. For a short period I worked in an academic lab which then helped me transition from the bench to project management when I went back to the private sector.

    Often I have bemoaned that society does not seem to value science and drug development in particular but I have been fortunate enough to work on interesting projects in developing novel therapeutics in many fields including vaccines, antibiotics, cancer, transplant rejection, rheumatology and cardiology. I can point to work that I have done with pride. However the lag between our scientific understanding and translating that knowledge to patients is immensely frustrating. I cannot help but envy the start up and venture culture that supports Silicon Valley and technology start-ups and their knack for changing the world over a time frame of years. In drug development our development timeframe currently stands at a decade or more so no wonder most venture capitalists are daunted.

    The impetus behind my choice to study biology and enter a career in drug development has been to improve human health and enable healthy aging to extend the time we live and enjoy life’s wonders. In my career I have been working in areas that have been somewhat peripheral (vaccines and antibiotics) as well as areas more directly related (transplant, cancer and cardiovascular) to healthy aging. I have gathered perspective on the challenges facing drug development and in particular the obstacles facing innovative therapeutics.

    I quit my job as Director of Project Management at a small biotech of the beginning of May to focus more directly on moving innovation forward on a wider scale than just one project or company. I applaud Aubrey de Grey’s efforts to drive forward the scientific efforts to attack the causes of aging through the Methuselah Foundation as well as the dedication demonstrated by the Life Extension Foundation. There is a compelling need for a more effective infrastructure developed to support the rapid advance of discovery into practice in human health. The innovation cycle in medicine currently is painfully long.

    The risks of this course of action are clear. Lack of income in the short term clearly creates risks in terms of security. I fear that I will be even less able to effect change as an external actor than within the system as an employee at a company. In this economic environment the risk of not being able to find employment or contract work looms large. BTW baring my soul in this post feels like I am at risk of public humiliation. However I look to the lessons I have learned in my past experiences and can see that the worst-case scenarios are not unmanageable.

    Over the next one to two months I will to connect with those with the means and the interest to support developing alternatives to the current drug development process including the examination of the most favorable jurisdictions for approving new therapeutics, use of Bayesian methods to generate and test hypotheses, outcomes based monitoring of healthcare delivery, crowdfunding in support of drug development and building compound libraries of novel natural products to provide new medicines for cancer, organ transplantation, infections and metabolic diseases.

    This is where I stand and I can use all the help I can get.

  30. I just started reading “The 4-Hour Work week” yesterday… Thanks for welcoming me to the party 3 years late! I am enjoying the book and was pleased to see this article after looking up the blog. Also, glad to make the contest deadline!

    I have worked mainly in Sales, since the 15 years after college. Just recently getting into Commission only Sales, before that it was mainly Salary plus Commission. I have worked many “jobs” (having worked through high school and college) and in many different career fields, too extensive to even summarize here.

    My “career positions” have been in these industries…Radio, Furniture, Newspaper, Telecommunications, Restaurant, Health and Nutrition, Travel, Automotive, etc.

    I have thought of my resume recently, which would be three to four (five?) pages in an eight size type, as an Experience and Continuous Learning ledger. As one manager once told me, “My dad said you are only as good as your Resume, meaning you’re only as good as your experiences”. I have had at least 100+ experiences if you count free lance and temporary Sales & Marketing jobs. Right now I feel I am good but, I am ready to be better (GREAT).

    I have already cut back my work hours over the last few years. First by flipping automobiles (local, nationally and even in one case internationally), in person and online. I have taken a risk with every car I buy. I have been reminded of this by people too much… They will be negative and say “What happens if you can’t sell it”, I dealt with this stress by not talking to those people about my business. Now I have an additional PT “job”, I am currently working 12-16 hours a week making $500-800 week, but it’s not automated! I have to go to the locations and sell people or I don’t get a check. Then and still now, even working a “job”, I get the same flack mentioned in Tim’s book…I am summarizing “Even though you can pay your bills and have money to do things, “Why aren’t you working full time then? You could make more.”” So far the book has really resonated with me in that way. It also has given me the push to say to myself…OK FINALLY…those 3 ideas I have to make it big, let’s try them one at a time….FINALLY!!!

    Even with having past success in commission sales in a quite a few different industries. In winning multiple sales contests and incentive trips, I learned that taking risks in a majority of cases was necessary to my success. (“Go Big or Go Home” was my mantra)……I am finally ready to improve and RISK AGAIN… My biggest risk was investing (my perfect credit) in a business I only had partial control in that ended up failing (guess what happened to my credit). This experience had given me a sense of worry in regards to risking again in that sense. Even though I have heard the statement successful people have failed many times, before they succeed, etc. It was the quote that Tim put in his book by Niels Bohr, “An expert is a person who has made all the mistakes that can be made in a very narrow field.”, that made me say “I am ready to become an EXPERT”. I hope I can learn and use, others failures (and my own past and future) to ramp up to this level quickly.

    Now it is no longer the pushed back Five Year Plan, it is now a Five Week Plan!!! Now it’s just a question of which I idea do I take to the next level first. That I where I would ask for your help and expertise. This is the change I want to make, taking one of the ideas I have and making it GREAT. I am not worried about “the risks”, I am ready.

    In the next 30 days I am looking at going from a “high school level” to a “PhD level” or “EXPERT” in the business sense with my business idea. In addition to speaking to (the EXPERTS), I will do this by finishing and implementing “The 4-Hour Work week” in my life. I will also pick up the other books by Tim, along with continue my reading of the blog. I now plan to read “The Start Up of You” by (the EXPERTS) Reid Hoffman and Ben Casnocha.

    I had thought of moving to where I would have the ability to get into a top notch business network, but now I realize I can stay where I am or go wherever and build that network. Thanks for the help!

    Thanks again,

    Jeff

    PS I was also reminded a couple weeks ago, in a random conversation while working my current part time job, that it most cases your success is measured by who you associate with. I was speaking to a guy that has had success in the Real Estate and Ticket Brokering Industries, without having a college degree. This didn’t prompt me to start calling or email celebrities or possible mentors…Tim’s book did…After reading the suggestion to contact “luminary-level business mentors” just yesterday. I have already contacted TWO, the first an ultra high profile business owner/investor and also a successful comedian, using Tim’s methodology. My initial contacts were through email and I got immediate direct responses. Now I am contacting three more here, by posting this comment. (and possibly even more?)

    PSS “SKY’S THE LIMIT” (MY definition….There is no LIMIT!!!)

  31. I just started reading “The 4-Hour Work week” yesterday… Thanks for welcoming me to the party 3 years late! I am enjoying the book and was pleased to see this article after looking up the blog. Also, glad to make the deadline!

    I have worked mainly in Sales, since the 15 years after college, just recently getting into Commission only Sales, before that it was mainly Salary plus Commission. I have worked many jobs and in many different career fields, too extensive to even summarize here.

    OK, my “career positions” have been in these industries…Radio, Furniture, Newspaper, Telecommunications, Restaurant, Health and Nutrition, Travel, Automotive, etc.

    I have thought of my resume recently, which would be three to four pages in an 8 size type, as an Experience and Continuous learning ledger. As one manager once told me, “My dad said you are only as good as your Resume, meaning you’re only as good as your experiences”. I have had at least 100+ experiences if you count free lance and temporary Sales & Marketing jobs. Right now I feel I am good but, I am ready to be better (GREAT).

    I have already cut back my work hours over the last few years. First by flipping automobiles local, nationally and even in one case internationally, in person and online. I have taken a risk with every car I buy. I am reminded of this by people too much… They will be negative and say “What happens if you can’t sell it”, I dealt with this stress by not talking to those people about my business. Now I have a PT “job”, I am currently working 12-16 hours a week making $500-800 week, but it’s not automated! I have to go to the locations and sell people or I don’t get a check. Then and still now, working a “job”, I get the same flack mentioned in Tim’s book…I am summarizing “Even though you can pay your bills and have money to do things, “Why aren’t you working full time then?”” So far the book has really resonated with me in that way. It also has given me the push to say to myself…OK FINALLY…those 3 ideas I have to make it big, let’s try them one at a time….FINALLY!!!

    Even with having past success in commission sales in a quite a few different industries…….I am finally ready to improve and RISK AGAIN… In winning multiple sales contests and incentive trips, I learned that taking risks in a majority of cases was necessary to my success. (Go Big or Go Home was my mantra) However, investing in a business I only had partial control in that ended up failing, had given me a sense of worry in regards to risking again in that sense. Even though I have heard the statement successful people have failed many times, before they succeed, etc. It was the quote that Tim put in his book by Niels Bohr, “An expert is a person who has made all the mistakes that can be made in a very narrow field.”, that made me say “I am ready to become an EXPERT”. I hope I can learn and use, others failures (and my own past and future) to ramp up to this level quickly.

    Now it is no longer the pushed back Five Year Plan, it is now a Five Week Plan!!! Now it’s just a question of which I idea do I take to the next level first. That I where I would ask for your help and expertise. This is the change I want to make, taking one of the ideas I have and making it GREAT. I am not worried about “the risks”, I am ready.

    In the next 30 days I am looking at going from a “high school level” to a “PhD level” or “EXPERT” in the business sense. In addition to speaking to (the EXPERTS), I will do this by finishing reading and implementing “The 4-Hour Work week” in my life. I will also pick up the other books by Tim, along with continue my reading of the blog. I now plan to read “The Start Up of You” by (the EXPERTS) Reid Hoffman and Ben Casnocha.

    I had thought of moving to where I would have the ability to get into a top notch business network, but now I realize I can stay where I am or go wherever and build that network. Thanks for the help!

    Thanks again,

    Jeff

    PS I was also reminded a couple weeks ago, in a random conversation while working my current part time job, that it most cases your success is measured by who you associate with. I was speaking to a guy that has had success in the Real Estate and Ticket Brokering Industries, without having a college degree. This didn’t prompt me to start calling or email celebrities or possible mentors…Tim’s book did though..After reading the suggestion to contact “luminary-level business mentors” just yesterday. I have already contacted TWO, the first an ultra high profile business owner/investor and a comedian, using Tim’s methodology, through email and got immediate direct responses. Now I am contacting three more here, (possibly even more?) by posting this comment.

    PSS “SKY’S THE LIMIT” (MY explanation….There is no LIMIT!!!)

  32. Hi! Thanks Tim for interesting posts. They are always read with enthusiasm and open up many new and useful. And this post isn’t an exception. Ben and Reid have raised a very important topic. Indeed, if you sue, the human mind is very inert and is caused by the evolution. stimulus – response. That’s what drives people. And if the stimuli have changed a lot in recent years, the response to them is still defined by an ancient evolutionary thinking. And it is not so simple to change it. There are a lot of recently published articles on this topic. They can be easily found on the Internet. But just think! After all, this our response is designed to protect us and provide the opportunity to continue our family line. And it really helped us over billions of years. Times change, and now we are becoming the hostages to these thought processes. But most important is that our consciousness has grown to such a level that has to understand it. And now, right before our eyes unfolds a fascinating picture of new evolution – the evolution of consciousness. After all, as you know, survives the fittest. And the fittest in this case is the one who will react to the modern stimuli in a modern way. In fact, Ben and Reid invite us to join on a new step of the human evolution!

    I am a just a simple guy who «was lucky» to be born in the countryside and, moreover, in a country with a dictatorial regime – in Belarus. I graduated in the best university of my country and after that went to the stable work. Nothing changed since the days of the Soviet Union. Everything for you have already decided here and life is very predictable. Eventually, I began to notice that I came in a comfort zone. I’m not particularly happy with the salary and work, but it is exactly enough for life. And you realize that something needs to change, but it is not enough will. The most dangerous aspect of the comfort zone is that it bogs down like a swamp! It sucks you. All around is clear and familiar, but if you change something you encounter uncertainty and ambiguity, and they are frightening. And you live an ordinary, dull, boring life. One wonderful day I caught myself thinking. I count every minute of the last working hour to leave the office quickly. Tim wrote in his book – Escape 9-5. In our country it is a little different – Escape 8-6. Then I decided that I can’t longer live like this and it’s time to change something. But it is so frightening to make the first step!

    Thus was the «Escape» plan born. Its main goal was to live a year without working in the office. For any reason! I made a simple table in Excel, and wrote down my monthly salary from the past couple of jobs. Below it summarized the annual income from them. Next I made a blank «monthly» column. I was going to write down in it all the money earned for the year. How and where I will earn them – I do not know. I signed a statement on the dismissal and started my «lifestyle» experiment. Now it is the end of June. Ends a year from the date of the decision. Ends an experiment. You are the first with whom I share my experiences. Looking at the table, I understand that the experiment was a success. To sum it up, in a year of free living I earned more money than at any of the previous works. But it was not easy! It was VERY not easy! The level of uncertainty was just off scale. Obscurity scared. Constantly attending thoughts: am I right? Constant accusations from the people who prefer stability but not new experience. And often it will be very close people. They are doing it with good intentions. But the notion of «good» for this time became different with them. And it was not easy. Especially in those moments when there was no money to live on. There is no constancy anymore. Actually forget about the constancy! «Good uncle» will not give you money at the end of the month. When money is tight or when money come to an end, brain begins to work very differently! It seems that the neural connections in it accelerate in hundreds of times. Believe me, if you take the path of a new experience – your brain will work the same way. And I reveal you one secret. When you come across uncertainty, suspense, fear. You will become very uncomfortable. And when its intensity becomes so big that it seems that a little – and you will not survive, there will be your main metamorphosis – you will no longer feel it! Simply, it will become the norm for you. This norm was once a swamp of the comfort zone. For me it is the main award of the experiment. And although I had a chance to work in different places, and sometimes the work was very difficult – I have no single drop of regret. I’m glad that I did so.

    There have been many changes during the year. And the chain of events led me to that place where I am now. I left the dictatorial country and now it’s almost a month since I live in Moscow. I decided to change my entourage that pulled me down, to the entourage that pulls me up. We can assume this is a new experiment. I am determined to start my own business here. I am writing you these words lying on the bed in hostel, and it is not much money in the pocket, but for me it’s not scary. I am no longer afraid of uncertainty and I am sure that I will succeed! I accepted the invitation of Ben and Reid to join on a new step of evolution. And you decide – will you accept it too. But believe me, it’s worth it!

    In my opinion, Reid would be interested to be my mentor, as this would challenge his comfort zone. Of course, it would be easier to help people from the States or any other developed country than the guy from the dictatorship of Belarus, who had just moved to Moscow, but there is a CHALLENGE. Opportunity for personal growth and progress. Through me you can discover new edges of yourself. And besides, the article said about «overseas opportunities». I am the great variant for this!

    Anyway, whatever happened, thank you guys and Tim for the great article. Any thinking person will find something to think about. You are just those guys who pull up.

  33. “What would happen if, gun to my head, I had to lose my job live in NYC?”

    I was unhappy in DC. All my friends were in New York and I was desperate to live there. But I couldn’t just pick up and go. Without money, I’d be screwed. If I lost my income . . .

    Wait . . . what exactly would happen if I lost my income?

    I wouldn’t die.

    No one was even going to hurt me.

    And if ANYTHING went my way . . . well, who knows what could happen

    So I called my friends. Made sure they’d be cool hosting me for a month (they were). I explored health insurance options if I lost my job. I planned my first unemployed day and made goals for my first 3 unemployed months.

    And the big one:

    I didn’t quit my job.

    I sat down with the President of the company to tell him about my plans:

    “I’m moving to New York in February,” I started.

    I thanked him for the opportunity to work there and for always treating me fairly. I told him over and over that my reasons had nothing to do with the work. Truth is, if we had an NYC office, I would have put in for a transfer. The company culture was awesome and I genuinely liked everyone I worked with. I just wasn’t happy socially in DC. If there was any way I could continue to help from New York, I was absolutely game.

    I was ready to be fired. But after talking over my plans, we realized there was still plenty of work for me to do remotely as a contractor. No one in at my level had ever done anything like it, but we agreed to give it a shot on a trial basis.

    Five months later, I’m working at the same job which I really like while living with my best friend in NYC!

    So what now?

    Now I want to mini-retire. I’m super appreciative to have the relatively stable paycheck, but one side effect of the contractor position I currently hold is that there are NO PAID VACATION DAYS. Any day I take off costs me money and threatens my continued employment. So when my friends are visiting Brazil this summer, I’m passing.

    I feel trapped by my paycheck again.

    The risk I want to take is to move somewhere FAR. Like 5000 miles away far. I want to spend a month (or two!?) living in Buenos Aires while maintaining my current position.

    Even though I’d be working just the same, it’d be the first time somebody worked remotely from outside the country. It’s a totally novel take on where and how work can get done. It might not go over well. They might decide to cut me loose and I’d have to start all over.

    I might struggle for a time. But I’ve realized over these past months that I’m going to be okay. I’ve got wonderful, supportive friends and family. I’m resourceful. I’m low maintenance. And I’ve got so much to gain.

  34. I have been a software engineer (coder), a product manager in the Valley for 6 years and currently lead teams at a prestigious tier 1 consultancy. I have a strong technology background and an MBA from a prestigious school. Now to answer your 2 questions.

    My plan for the next 30-60 days is to change jobs and find a career. One I am passionate about and wake up feeling lucky to have. And also one that allows me to spend time on what matters to me outside of work. I know it has to involve innovation, technology and building a product / company that has an outsize impact. Having done at least two of those before, I know I enjoyed it.

    The risk is the impact of my decision on people who depend on me. My son, my wife and to some extent my parents. The other risks are lost time and doing without (getting used to). But there is a bigger risk of not following this path. In 30 years, I want my older self to look back on life with satisfaction and with a sense of accomplishment and not with regret and “what if”s. Just for that alone, this change is imperative. There is the obvious risk that I am walking away from not insignificant sums of money and a life of comfort if I stay. But I have never made decisions for money alone. I am not about to start.

    To do it alone or find someone (person / company) who is, boils down to finding someone who can see my “high learning clock speed” and hunger to succeed.

  35. Guys,

    Great article. I am currently reading the Carnegie book How to win friends and influence people and I put it down to read this post and I see the teachings implemented perfectly by you three.

    I am 33 years old and have been a trader for a hedge fund since 2003. I quit last September to partner up with my best friend and now business partner to pursue the business we have been always talked about and decided it was time for action. So, the decision has already been made. Now to the risk part. I have enough money saved and to invest into my business which would last me me about a year and a half if I was to receive no paycheck at all. I rented out my apartment and cut my bills in half to give myself piece of mind. We launched in January of 2012 and we are currently growing pretty nice but we need capital and have began setting up initial rounds of funding with angels and family/friends interested in contributing.

    I’ll tell you what, I am scared as hell. I don’t know what the future holds, but, I believe in our product and I believe in myself and my partners willingness to see this through and make it a success. So to me the risk is pretty big right now. I know it and am aware of it but I know I am not stopping until this blows up.

    Since reading 4 hour work week I don”t think I have worked less than a 14 hour work day so far lol. But I jump out of bed every morning psyched to make this vision become a reality. Keep up the great content guys I love reading your stuff. Thx – Paul

  36. Interesting article and great comments as well. For me risk isn’t just a basic par t of life, it’s the source of life. Most of the risks I’ve taken have led me in directions I never would have thought or dreamed, for example leaving my home town and coming to New York with just a couple hundred bucks in my pocket and all my earthly possessions in a duffle bag. Now I’m in the next phase of my life, middle age and looking forward to pivoting to the next adventure. I left the corporate world back in January and since then have found a number of interesting freelance projects and recently a business partner. Our plan is to start up a social media company to help other business build, nourish and protect their brand. First phase is to help healthcare professionals and companies with navigating through the maze of options and giving them customized help and guidance. I also believe risk is about diversity, so I also intend to plant a few other seeds/ideas in the market – including a mobile app to enable instant networking, location based service to help you connect with other like minded business folks while your on the road and urban incubators, crowd sourced funding for ideas that improve city living. The other risk I want to take is to encourage other baby boomers to keep pivoting, it’s never to late to try out something new.

  37. To make a long story short, here is where I am now. I’ve been working at my current job for 3 years. This job is unfulfilling and is used primarily as a means of obtaining a steady stream of income. Losing this steady paycheck is the factor that keeps me from quitting my job and pursuing something I am more passionate about.

    From the post my job is considered “low-risk”; I’m currently an engineer for a defense contractor. I don’t like my job and I’ve thought of it as a necessary evil. This post made me realize that working a job which “pays less in cash but offers tremendous learning” might be a risk I am willing to take.

    My dream is to become heavily involved within the CrossFit community and to open and run a CrossFit gym. [FYI: CrossFit is a type of fitness program.] Recently I’ve gotten really into it, going 5 times a week. I have seen a transformation in both my physical and mental health in the last 4 months than I have over the past 2 years going to a regular gym. The feeling of self-confidence it has given me is incomparable. Transforming my body and mind is an eye opening experience that I want other people to feel as well as help other people achieve their fitness and overall health goals.

    What change do you want to make in your career in the next 30-60 days?

    What I would be willing to risk in the next 30-60 days is my current job to pursue an in-depth knowledge of CrossFit, experience coaching CrossFit, and work towards opening my own CrossFit gym. In the next 30-60 days I’d like to get my “CrossFit Level 1 Certification”. I would like to work closely with a reputable coach learning from his or her past and current experiences teaching CrossFit. I would like to work for a CrossFit gym gaining experience coaching classes as well as working with coaches during personal training sessions with clients. Ultimately I would like to raise enough capital to start my own CrossFit gym in Manhattan. I’d like it to be parkour/freerunning, like a blend of Tempest Freerunning and CrossFit.

  38. SHARKMAN & MANTAGIRL need your help ditching lucrative careers in travel/tourism to CREATE A STARTUP that helps people find the coolest adventure travel jobs in the world. We’re also headed on a 1 year AROUND THE WORLD trip on NO MONEY DOWN to show the world you don’t need a big bankroll to travel the globe and have amazing adventures. We’ll be writing a book that will be high adventure meets how-to guide. Sound pretty cool? Hit us up!

  39. )

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    ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^

    In short, this is a comment about breaking away from the certainty of a career in law and, by offering FREE labor, get a high-level assistantship with a tech or marketing company.

    Why the fire picture above? Two reasons. First, as a way to get noticed in a sea of comments. I think we can risk, get noticed and matter, or we can blend in and die irrelevant. The choice is all ours.

    But the picture above also symbolizes the fear of risk. When I think of it, fear of taking risks is like a fire: small and managable can give warmth and help you posper, yet once too big, can paralyze you from concern of getting too close, or if too close, burn you to death.

    Starting this comment with fire is my risky “choice” to embrace that fire. Except that in this brand new world of ours, as The Startup of You suggests, taking risks is a choice no more. It’s a necessity. A necessity stemming from the need to stand out, to push past the crowd, the business as usual, the 9 to 5 for 9 to 5’s sake, to be part of this tribe of early adopters, to dare to be different.

    It’s a necessity especially today, when in a flat world of ever decreasing entry barriers, anyone can be the same. It’s a necessity because this flat, unbound world is not much different from a blog article like Ben and Reid’s, with a sea of comments, where all you see is the sea and not the individual water-like comment molecules that make it.

    What spoke to me from The Startup of You, in essence, is that while taking a risk with one’s career will not eliminate risk itself (after all, it’s systemic), it might just be the best insurance from irrelevance, because deep down, we want our existence and our life product to matter. I think the most fundamental question to ask about anyone or anything under the Sun (be it an action, event, product, business, non-profit, person, idea or risk) is: does it (s/he) matter? The Startup of You helps so that in the end, you may answer that question for your own life with a resounding YES.

    Here is how I want to matter, what I want from you Ben and Reid, and what I’m willing to do for it:

    I want an in-house assistantship with a high-level entrepreneur, preferably in a tech or marketing company. And, Ben and Reid, since you are trying to help me, the least I can do is make it as effortless as I can for you to reach your goal. While I realize there is no such thing as a free lunch, I can get as close to it as possible by working for free, working a lot, while requiring virtually nothing.

    I will work for free. I have 14,916 dollars and 58 cents saved in the bank and will work for free for as long as that money will last (and trust me, I can make it last). Getting paid would be great, but I’m not planning on it, as experiential knowledge and having the chance to learn from a great mentor is infinitely more important.

    I will work a lot. While the proverbial “nothing was handed down to me” applies, examples might prove more helpful. First, because my parents could not afford to send me to college, i worked full-time while going to school full-time, graduating debt free. Also, 60 hour weeks were a common occurence building a Wall St trading firm, but just as common were the 100 hr weeks during its last dying breaths in the peak of the Great Recession.

    I don’t need much. Phrases like “company perks” and “during business hours” don’t apply to me for I am hungry and I am humble. I don’t need a company computer, personal office, fancy title, job description or relocation package. I will do what needs to be done, and if that means having to clean the floor, I will do that too.

    Lastly, I don’t need to be babysat. Having sat on both sides of the proverbial hiring table, I deeply understand the management-employee relationship, what it means to “own a problem,” and believe that a good attitude is at the center of the work universe.

    What am I giving up?

    The two main risks we take seem to be either to survive or to thrive. Survival risk grows out of our long evolutionary hard wiring (as you point out), scarcity thinking and the necessity to meet our immediate needs – e.g. old company downsized so now one searches for a new job, albeit in a different industry. Bu upon closer observation, this type of risk is no risk at all because the alternative (the jobless status quo) sucks. Thriving, deliberate risk is true risk. It is not born of necessity, and as you note, innitially appearing as a worse alternative to the comfort of the current status quo. I’d like to think the risk I’m taking is a deliberate one, not because I have to, but because I can thrive in it, forgo short-term safety for long-term growth.

    I just graduated from law school and have a good law job lined up. In short, by taking the “risky” path I suggested above, I risk forgoing and likely “will” forgo – at least definitely in the short term – the financial safety that comes with working at a law firm, giving up the savings I have accumulated, leaving behind the certainty and comfort of the environment and people I have known, or just looking plain foolish in general.

    I also have a big fear of screwing up and making both you Ben and Reid look bad for recommending me (I have yet to make a recommender look bad, but maybe it’s because I am so afraid of it 🙂

    While, by living the comfort of law, I will risk a lot of external, safety oriented things, what I will not risk is what drew me to law in the first place, the ability to analyze problems and manage the risk in each. When I think of lawyers, I think of risk management machines, looking at the downside, costs and flaws more than anything. Just as the sole function of a speed governor in a car is not to let you go past that speed of no return, it is the job of a lawyer to manage and calculate risk for a living. So, generally speaking, lawyers are very risk-averse and one of the least likely groups to make unusual shifts in career.

    (Side Note: As i started to write this comment, my risk governor kicked in, calculating the risks of writing this comment and the trade-off between the highly uncertain rewards of winning a contest and the dead sure sunk costs of lost time. I had to actively shut up the lizzard brain that was whispering “shouldn’t you be studying for the bar”?)

    Here are some things I think I’m good at and that you might find useful when trying to help/pitch me to any potential high-level entrepreneurs:

    * Sales

    I started selling when I was 9 years old in my home country (out of necessity really, when both of my parents were let go of their jobs because of their political beliefs) starting as an ambulant seller of chocolates, chewing gum and tabacco, and progressing to a flea market business of shoes, buckets and silk flowers that my whole family continued operating for 8 years. Best thing that ever happened to me.

    I sold ballroom dance lesson programs – to the extent that one of my students casually observed she had spent more in buying dance lessons from me than she had spent in her new Mercedez. I also taught and competed in ballroom and latin dancing .

    I cold called and rased funds on Wall St (as noted above).

    * Advertising and Marketing

    I supported myself through law school writing ad copy and advising on branding and marketing strategy businesses from large gaming companies in Bulgaria to solo practicing attorneys in the U.S.

    * Law

    I can help with anything legal, having previously worked for top brands’ legal departments. The experience gained in the business world helps me better understand legal issues at the intersection of law and business.

    * Human Resources

    I have hired and fired, but can also follow directions well, considering my positive attitude as my greatest asset. My greatest passion is the study of people, how to read and relate to them.

    * Learning

    The learning bug got me. From the fluency of foreign languages, to the ass kicking of Mixed Martial Arts, I enjoy learning new things about people and the world more than anything.

    In closing, through this assistantship, I want to go on to change the world, leave my mark on it while bettering the lives of those around me. However, if my free work can as much as get that entrepreneur mentor I may have the chance to work with to spend five less minutes at the office and five more minutes with family while leaving me richer in friends and know-how, I would have changed the world already.

    Best,

    Orge

    P.S I have found that genuinely helping others get what they want, brings the karmic boomerang back, often multiplied. Even beyond the scope of this contest, if my skills and past experiences would be useful to you or can fit in any way to help in the pursuit of your lives’ mission statements, ping me. I’d love to help.

  40.  Hi, I’m Orge

    In short, this is a comment about  breaking away from the certainty of a career in law and, by offering FREE labor, get a high level assistantship with a tech or marketing company.

     

    When I think of risk, I think of when man first discovered fire. What was that like? What was it like approaching it? Something so frightful and dangerous. Fear of taking risks is like that fire: small and managable can give warmth and help you posper, yet once too big, can paralyze you from concern of getting too close, or if too close, burn you to death. 

     

    Starting this comment with fire is my risky “choice” to embrace that fire, to risk, get noticed and matter, or blend in and die irrelevant. The choice is in all of us. Except that in this brand new world of ours, as The Startup of You suggests, taking risks is a choice no more. It’s a necessity. A necessity stemming from the need to stand out, to push past the crowd, the business as usual, the 9 to 5 for 9 to 5’s sake, to be part of this tribe of early adopters, to dare to be different. It’s a necessity because in a flat world of ever decreasing entry barriers, anyone can be the same. It’s a necessity because this flat, unbound world is not much different from a blog article like Ben and Reid’s, with a sea of comments, where all you see is the sea and not the individual water-like comment molecules that make it.

    In essence, what The Startup of You suggests is that while taking a risk with one’s career will not eliminate risk itself (after all, it’s systemic), it might just be the best insurance from irrelevance, because deep down, we want our existence and our life product to matter. The most fundamental question you can ask about anyone or anything under the Sun (be it an action, event, product, business, non-profit, person, idea or risk) is: does it (s/he) matter? The Startup of You helps so that you may answer that question for your own life with a resounding YES.

     

    Here is how I want to matter, what I want from you Ben and Reid, and what I’m willing to do for it:

     

    I want an in-house assistantship with a high-level entrepreneur, preferably in a tech or marketing company. And, Ben and Reid, since you are trying to help me, the least I can do is make it as effortless as I can for you to reach your goal. While I realize there is no such thing as a free lunch, I can get as close to it as possible by working for free, working a lot, while requiring virtually nothing.

    I will work for free. I have 14,916 dollars and 58 cents saved in the bank and will work for free for as long as that money will last (and trust me, I can make it last). Getting paid would be great, but I’m not planning on it, as experiential knowledge and having the chance to learn from a great mentor is infinitely more important. 

    I will work a lot. While the proverbial “nothing was handed down to me” applies, examples might prove more helpful. First, because my parents could not afford to send me to college, i worked full-time while going to school full-time, graduating debt free. Also, 60 hour weeks were a common occurence building a Wall St trading firm, but just as common were the 100 hr weeks during its last dying breaths in the peak of the Great Recession.

     

    I don’t need much. Phrases like “company perks” and “during business hours” don’t apply to me for I am hungry and I am humble. I don’t need a company computer, personal office, fancy title, job description or relocation package. I will do what needs to be done, and if that means having to clean the floor, I will do that too. 

    Finally, I dont need to be babysat. Having sat on both sides of the hiring table, I deeply understand the management-employee relationship, what it means to “own a problem,” and believe that a good attitude is at the center of the work universe. 

     

    What I am giving up?

     

    The two main risks we take seem to be either forced (surviving) or deliberate (thriving). One grows out of scarcity thinking and the necessity to meet our immediate needs – e.g. old company downsized so now one searches for a new job, even in a different industry. This type of risk is no risk at all because the alternative (the status quo) sucks. Deliberate risk is true risk, not born of necessity and as you note, innitially appearing as a worse alternative to the comfort of the current status quo. I’d like to think the risk I’m taking is a deliberate one. 

    I just graduated from law school and have a good law job lined up. In short, by taking the above proposed “risky” path, I risk forgoing and likely “will” forgo financial safety, prestige, giving up the savings I have accumulated, leaving behind the certainty and comfort of the environment and people I have known, or just looking foolish in general. I also have a big fear of screwing up and making both you Ben and Reid look bad for recommending me (I have yet to make a recommender look bad, but maybe it’s because I am so afraid of it 🙂

    While, by living the comfort of law, I will risk a lot of external, safety oriented things, what I will not risk is what drew me to law in the first place, the ability to analyze problems and manage the risk in each. When I think of lawyers, I think of risk management machines, looking at the downside, costs and flaws, always analyzing them more than any potential benefits. Just as the sole function of a speed governor in a car is not to let you go past that speed of no return, it is the job of a lawyer to manage and calculate risk for a living. As a side note, as i started to write this comment, my risk governor kicked in, calculating the risks of writing this comment and the trade-off between the highly uncertain rewards of winning a contest and the dead sure sunk costs of lost time. I actively had to shut up the lizzard brain that was whispering “shouldn’t you be studying for the bar”? 

    Here are some things I think I’m good at and that you might find useful when trying to help me:

    * Sales

    I started selling when I was 9 years old in my home country out of necessity, when both of my parents were let go of their jobs because of their political beliefs, starting as an ambulant seller of chocolates, chewing gum and tabbacco, and progressing to a flea market business of shoes, buckets and silk flowers that my whole family continued operating for 8 years. Best thing that ever happened to me. 

     

    I sold ballroom dance lesson programs – to the extent that one of my students casually observed she had spent more in buying dance lessons from me than she had spent in her new Mercedez. I also taught and competed in ballroom and latin dancing . 

     

    I cold called and rased funds on Wall St (as noted above).

    * Advertising and Marketing

    I supported myself through law school writing ad copy and advising on branding and marketing strategy businesses from large gaming companies in Bulgaria to solo practicing attorneys in the U.S.

    * Law

     I can help with anything legal, having previously worked for top brands’ legal departments. The experience gained in the business world helps me better understand legal issues at the intersection of law and business.  

    * Human Resources

    I have hired and fired, but can also follow directions well, considering my positive attitude as my greatest asset. My greatest passion is the study of people, how to read and relate to them.

    * Learning

    The learning bug got me. From the fluency of foreign languages, to the ass kicking of Mixed Martial Arts, I enjoy learning new things about people and the world more than anything.

     

    In closing, through this assistantship, I want to go on to change the world, leave my mark on it while bettering the lives of those around me. However, if my free work can as much as get that entrepreneur mentor I may have the chance to work with to spend five less minutes at the office and five more minutes with family while leaving me richer in friends and know-how, I would have changed the world already. 

    Best, 

    Orge

    P.S I have found that genuinely helping others get what they want, brings the karmic boomerang back, often multiplied. So ideally, before telling you about what “I” wanted from you, I would have liked to know a bit more about what “you” want to accomplish. Even beyond the scope of this contest, if my skills and past experiences would be useful to you or can fit in any way to help in the pursuit of your lives’ mission statements, ping me! I’d love to help. 

  41. Hi I’m Tim.

    If you asked me where I want to be 5 years ago while in University I would have described something very similar to my current situation. I am working as a marketing manager on high level marketing projects at a + $100m company with quite a bit of freedom to experiment with my budgets. I have everything I thought I needed 5 years ago: a nice house, two cars, great friends & an amazing fiancée. At 28 I am not ready to settle into a boring comfortable 9-5 lifestyle without trying something big.

    After about a year of introspection and self help books (4HWW, The Power of Full Engagement, The Magic of Thinking Big, Finding your Dream, Ramit Seti’s Earn 1K etc…) I decided to set some new goals that I am forcing myself to start/test over the next couple of months. Ideally I would like to end up spending half of my time traveling and working on my photography and the other half as a marketing consultant / entrapaneur.

    In the next couple of months I plan to make actual steps towards this goal but have been slow to get started due to my fear of the perceived risks. I’ve outlined my steps as such:

    1. Launch a small business to prove to myself that I can make money on the side

    2. Begin taking more control of my time at work and getting my employer more comfortable with me working from home more often

    3.Get more efficient with how I spend my time and manage my energy

    4.Getting my portfolio/resume out there and having headhunters calling again so that I do not feel as insecure about losing my job

    Some of the risks I worry about are my work finding out about my side projects and demanding that I stop them or fire me. One of the biggest risks I see is trying all this out and finding it accomplishes the opposite by sucking all my free time and leaving me miserable. Lastly I worry that if I push my boss and work too hard on the remote working side they will fire me and I will lose my comfortable lifestyle.

    I have already paid for and am launching the first marketing campaign for my business so that I will be forced to deal with potential customers instead of worrying about potential negative outcomes (for example them calling me at work and me getting in trouble). This will be happeningby the end of the month.

    I have in the past year dabbled with some of the 4HWW techniques such as outsourcing but have been to worried about the risk of diving in. I figure that if I don’t do something now I will find myself 20 years from now regretting not trying something bigger.

    Any advise you have would be helpful.

    Kind Regards,

    Tim

  42. – What change do you want to make in your career in the next 30-60 days? (e.g. Change jobs, ask for a raise, find a new opportunity within your company)

    – How are you thinking about the risk involved in this move?

    By September 1st, I want to relinquish 75% of my day-to-day activities for SolSolution so that I can focus the majority of my attention on raising $5M, so we can be the leader for solar powered schools. First, this requires having a fully trained sales team, with a defined process, that clearly communicates our powerful message to schools. Second, our operations team will have to be comfortable maintaining the growth of our entire team and operations, with very clear responsibilities and goals identified.

    The specific potential risks that I foresee in making this change include:

    – Lower quality first meetings with schools.

    – Potential for adverse affects on our reputation and brand.

    As a founder, I have intimate knowledge of the intricacies of our business, passion for the customers we serve, and authority to definitively say what we can and cannot do for schools. This translates into a high level of trust from our school partners very early on in the process. Our young team, on the other hand, has less experience in the solar industry and has spent less time in our organization. By removing myself from much of this sales process, our younger team may not have the knowledge to confidently answer all questions from school administrators. Additionally, they do not have the technical credentials that I do, which stands out to school contacts I talk to and allows me to leverage my capabilities in science and technology to quickly create (future) technical solutions on the fly. Finally, they may not have honed the SolSolution message to schools like I have, in a way that is infused with passion.

    *** The biggest risk, though, is lack of massive scalable impact for our schools and environment. ***

    If I don’t face these risks and lessen their potential, by training and building our team properly, then the biggest risk is not enabling massive change in our world. If I don’t focus my efforts on raising enough capital to really build our business, then we will never create a legacy of impact that makes a meaningful difference for students across our nation.

    To bring solar power to schools across the nation, I have to change the investment of my time in SolSolution. I can’t let fear of these risks prevent us from doing what we need to do at some point, regardless: build a high-performing sales team that performs way better than I ever could.

  43. I’m totally averse to the massive risk of:

    An inept Employer wrecking my future.

    A single – source income stream that could collapse overnight.

    Not knowing if my retirement is sustainable due to unstable pension funds.

    Which is why I took the long – term sane option: going without short – term gratification and running my own business for fifteen – plus years.

    I failed three times over, each time I fell less heavily through experience.

    Then I hit my current sweet spot, which is blossoming beautifully; lately I’ve been fortunate to be approached by a number of very serious businesses and formed strong passive income yielding alliances.

    But the real Result? I got to tick along on less than four hours work per week in 2011, caring for my extremely ill Fiance. PRICELESS.

    Now I’m back to active growth and loving the low risk of controlling my own future.

    Will I diversify into new ventures? Hell yes. It’s fun – good safe fun.

  44. Over the next couple of months, I’m working on opening an online business in the art industry. The goal is to start making some extra cash, do something I really enjoy, and eventually replace the income of my current job so I can spend more time with my family. Finances are a minimal part of the risk– the bigger risk is the feeling of personal failure and the loss of all the time put into the business if it doesn’t work out, plus the subsequent hesitation to try again. The only option to keep going is to perceive the much greater risk of never trying. If I don’t take the leap, success isn’t even an option.

    The bonus of making this change will be helping others define their success while reaching for mine– one of the large components of the business will be to help artists learn to take their own risks and become successful at their craft. It’s so much more worth taking the chance when it can have a positive effect on others.

  45. Ben and Reid,

    My friends call me Franco. Out of college I took a job with a Fortune 500 company and ended up leaving within a year to pursue a dream of playing professional soccer. Although it didn’t turn out as I had dreamed, it provided the opportunity to go to other countries and compete with some of the best players in the world… This became example #1 as to why taking my risk and “failing” was better than not taking it and still being a desk jockey like most of my friends (whom I still love).

    This lead to living in Costa Rica for 6 months for $5 a day and making things happen without financial help from family or a savings account. Then enter the love of my life… the risk adverse health care professional. Things changed, I took an opportunity to get my MBA (most of it paid for on scholarship). Graduating from the MBA program was a turning point. Do I go the “safe” and “secure” route my wife (and her family) prefers or do I try to make something happen outside the box.

    Here is where the corporate “ceiling” (Gosh I’m using a lot of ” “) really comes into play. Almost everything becomes fixed (pay, vacation time, time/experience before promotion, ect.) except for your hourly work load. I found a happy medium with my wife and took a flexible sales job (for less than half the money most of my classmates made) and started a baseball blog to hopefully become a future “stable” job that I love (and with no ceilings!)

    Here I am about 18 months later living in the Dominican Republic (with my awesome wife) working remotely 15 hours a week on my sales job and pouring the rest of my time into my baseball blog. The BIG GOAL now is to quit my sales job and be able to support my family through the baseball blog full-time by August 15th. It’s a difficult sale for the wifey to get on board with something that doesn’t come with benefits and set income, and that has lead to a ton of deep conversations. I really feel that making 10k in a month would help ease those worries. (I’ve only made $1000 in the last 2 months, but I’m a couple breaks away from making big things happen.)

    With your help, there is no doubt that I’ll get to that Next Level sooner rather than later. Thanks for your consideration in this contest.

    And thanks for the awesomely timed article for me (entrepreneur/”risky” guy) and the wifey (recently quit her health care job).

  46. – What change do you want to make in your career in the next 30-60 days? (e.g. Change jobs, ask for a raise, find a new opportunity within your company)

    – How are you thinking about the risk involved in this move?

    I am a 21-year-old freelance trumpet player from San Diego who currently slings pancakes (restaurant server) to pay the bills. I recently had my first big break on the hit TV show Glee (playing trumpet).

    July 1st I’m quitting my job as a restaurant server in San Diego, moving all my belongings to a new apartment in Los Angeles and departing for Spain July 2nd. I’ll be traveling around Europe for 2 weeks and then I’m returning to LAX for a 12 hour layover and then going straight to Ecuador to teach music with a nonprofit organization. August 8th I’ll be returning from my adventure (inspired by the 4HWW).

    When I get to Los Angeles, I’m going to jump full force into marketing myself as a freelance musician. My goal is to back a famous pop-star for example Lady Gaga or Lenny Kravitz etc.

    I have a lot of ideas about reducing the risk of this move, some of which I have already begun to act on.

    -I have contacted as many pop trumpet players who back famous artists and so far I have had great success in talking with John Legend’s trumpet player (Clayton Reilley) as well as Lady Gaga’s trumpet player (Brian Newman), I actually just returned from NYC where I met Brian who had some incredible advice and insight for me.

    -I have photo shoots scheduled with some very talented photographers/videographers who want to offer their services for free to build their resumes.

    -I’m going to use the content to create a great looking website with a 2 minute video that artfully showcases my playing. The website will also have links to other social media websites that provide my current gig schedule and blogs etc.

    My biggest obstacle is going to be paving my own path, there is no set path for landing a gig with a big act as there is with becoming a doctor or a lawyer etc. I’m going for it and I’d like to thank both Ben and Reid in advance for all the help.

    sincerely,

    Matt Davies

  47. As an introduction, I have worked in bulge bracket investment banking and megafund private equity for the last 5 years. Over the past couple years, I have been itching to start my own company in the internet space. Although I continually debate if it’s the right move, I feel like the time is now.

    I have been interested in entrepreneurship since starting a company in high school, studying entrepreneurship in college, and viewing my current finance experience as a chance to learn as much about how companies operate in as short a period of time as possible while stashing a good chunk of cash. However, the longer I stay working in finance the tighter the golden handcuffs become. I am currently in a career track role, manage a fair amount of people, and make good money. I can rationalize to myself that the higher I climb in corporate America, the better it will be for my resume and my ability to attract capital in the future. However, my burning desire to start my own company only grows over time. I can’t describe the appeal to have complete ownership over a company and its culture, grow an asset over time that I am deeply passionate about, employ and empower people, and feel excited to go to work every day. My current job takes up all of my time (work 80+ hours/week) so I have not had the ability to vet my business idea or try to start a beta version on the side. The fact that my idea has no traction at this point and I would really need to quit my job cold turkey in order to pursue an entrepreneurial venture increases my fear of failure. That being said, I have no obligations holding me down and if I am truly going to start my own company, there really is no better time than the present.

  48. I want to ask my mobile app consulting firm to trust me with $3,000 – $5,000 to spend on designing and developing an innovative and profitable app/service, and ultimately prove to them that I can lead a successful internal product development effort.

    To provide some background, our young company focuses on creating apps for an assortment of clients (from Fortune 100’s like Nike and Sony to smaller, lesser known non-profits and businesses). Although we have been quite successful in this pursuit, I feel that we have a hunter-gatherer business model and that there is abundant opportunity for us to strengthen our own brand by creating compelling products and services.

    My strongest asset is my creativity, and my deepest passions are fueled by entrepreneurship and social innovation. I feel unfulfilled and underutilized within my current role. Unfulfilled, because at the end of every 12-hour day, I don’t feel as if my hard work truly benefits anyone outside of our client-vendor relationships. Underutilized, because I feel relegated to a role that doesn’t play off of my greatest strengths and ambitions. My long term goals involve pioneering my own businesses, but right now, I want to create an opportunity for myself that I would find genuinely fulfilling – something that I can pour my passion and energy into, and greatly profit my company and society in the process.

    Instead of slowly paying my dues and building up trust incrementally as a new developer and project manager, I want to take a huge risk and propose a few ideas that are worthy of a small investment and lot of faith. With only a year of experience under my belt, I know this is a bold and risky play. I know exactly what I want, but I am unsure on how to approach my management team. Any help and inspiration is greatly appreciated. Thanks for reading!

    Best,

    Randy

  49. thank you for this post! my thoughts on this: I’m ready to cross the river and go after that fresh deer carcass. that dead deer is looking real good about now. I’ve been stuck working for the government (‘safe’) for 7 years now–that fact alone is putting the fire under my butt to cross the river. my career is not exactly ‘fragile’–I’m an urban planner–but my type of employment is. on the other side of the river, I’m working for myself, following my interests, perhaps even hiring people who share my hunger for venison. I would take a pay cut for more freedom in my life. the awesome irony is that if I pursue what I love in the right way, I’ll make more money.

    I think I just needed a swift kick in the bum toward that river. this post, and many like it, helped. I’ve got that tendency to think I need everything to be perfect–I need to learn every aspect of a thing before jumping in. but you learn as you go. I have to keep reminding myself of this–you go live with something that’s not quite ready, and you make it slightly better next time. you ready fire aim, ready fire aim, ready fire aim. your aim gets better every time, but you’ve got to fire before you know how bad your aim is and what you need to fix to get closer to your target next time. (wait, isn’t the deer already dead? I’m swamping myself in metaphors).

    I become intensely interested in topics for a span of time, long enough to become proficient, to learn the subtleties. it was a distraction before, but now I’m going to make use of that trait. I’m going to be making products of everything I learn. I’ll start with instructional stuff. the winners will move on, the fit will survive. my career is about to start an evolution. and I know that the first $10 I make online will be super powerful. it will signal my brain that this is possible, this is a reality within reach, that I’ve reached the dead deer, and there are plenty more dead deer waiting for me up ahead, while most people are still ‘safe’ on the other side of the river.

  50. My name is Erin and I have a situation that’s all-too common.

    I graduated from school with a BS in engineering and three high-profile internships under my belt. I felt destined for stardom when I fell in love with a guy in the military. He couldn’t quit his job so I moved with him thinking that moving half-way across the country where I had no connections wouldn’t prove too much of an impediment. Six months of unemployment later (about which I was completely stunned) I adapted to market realities and transitioned to my first Plan B and got an excellent job with an insurance company. Things were looking up when my husband got a transfer assignment for ten months. Thinking there was no way I’d be hired at a decent job for such a short amount of time I dropped out of the workforce and had kids. (Plan Z #1)

    That was six years ago.

    Being a stay-at-home mom (SAHM) hasn’t been easy. There were several times I wanted to throw in the towel and go back to work, particularly during his deployment. But now I have a gaping hole on my resume. The few recruiters I’ve talked to have had demeaning advice like “try applying to work retail” or “sale stuff from home to your friends for money”. I have seen my competitive advantage dwindle to nothing and feel thoroughly Mommy-Tracked.

    Now my eldest is starting Kindergarten and my youngest will start preschool, freeing up some daily time. My main big assumption here is that my husband will stay in the military and that our family will continue to move around every few years. This will make having a good job very difficult as companies would be reasonably unlikely to hire someone who wouldn’t be around long. I see my options as follows (yes I made lists and spreadsheets):

    -Stay a SAHM. The pluses are that the food is better and I’ll have more free time to devote to exercise and socialization. This option has the most opportunity cost in terms of financial risk. There’s also a fulfillment risk in that the joy of being a SAHM is very much dependent on your co-workers (the other SAHM’s) which are location and finance dependent. We can afford more (MUCH more) in more rural vs urban areas and we won’t have control over that. This is both Plan A and Plan Z at this point.

    -Get a Part-Time Job. This is a bit trickier and includes everything from working retail (to fill the gap and learn various skills) to starting my own business (iPhone apps, helping run a local non-profit). The pluses of this include being mentally stimulated. There would still be an opportunity cost more associated with the social, chronological, and financial risk of the time commitment. Starting my own company would take finances of which I have a small amount. I would have to pay for some childcare and see a huge reduction in free time (of which I currently have none). Fulfillment risk doesn’t go away as there’s no guarantee that this would actually increase my happiness.

    -Get a Full-Time Job. This would be difficult because since I have no idea even what industry to enter and we’ll be moving around often so I’d be perpetually entry-level for the next decade. The positives are that this would offer the most in terms of stimulation. The main risk would be chronological (massive time commitment required) with the fulfillment risk coming in terms of the reduced social life.

    In an effort to prioritize learning I’m thinking about doing a hybrid of plans 1 and 2; staying a SAHM while volunteering at a local small business and non-profit to learn the ins and outs of those businesses. It would fill up my resume and not cost anything. The downside of this plan is that since there’s minimal risk involved I can’t be sure I’m not picking it out of cowardice. I also have no guarantee I’ll be able to use these things when I put them on my resume since I have no idea even what industry would be a good fit for me at this point. The main risk is choosing through procrastination. Within the next 60 days (Kindergarten starts in exactly 60) I want to have chosen my option and to begin executing my new plan.

  51. I read this article because I am dropping out of dental school to focus on my app development business. I am $250,000 in debt and have been in college for 7 years. My family, friends and colleagues will stare shamefully at me and shake their heads. Anyone Ive mentioned this to looks at me like I just murdered someone. No one is on my side.

    Ive finally decided to say NO, I will not do this just to be stable or look good. I refuse to do something my whole life that I despise. I originally went to dental school for approval from my parents, my friends, girls, etc. As Ive matured, I realize my youthful lust for acceptance and stability has become a prison. I do not want a life sentence. I have a passion for this app that Ive never felt before. It makes me feel like im finally living and creating. This is what I was made for. I love this feeling.

    Some friends and myself have worked hundreds of hours and spent $8,000 on the iphone/ipad app we are about to release. It is a repeatable business model that I know will work. Even if it doesnt, Id rather be a god damn garbage man in the day and work on my own projects at night than to be stuck in this hell for eternity.

    My mind was already made before I read this article but after reading the first few paragraphs I realized why I did not drop out years earlier, even though I knew I should have. I had a stable, respected career path. Even though I hated the path I was on, the risk of finding a new one was terrifying. The public disapproval and drastic change goes against everything my primate brain says. This article taught me as much about my brain/body as years of intense anatomy/physiology/biochemistry classes. I wish I could have read it earlier in life. Thank you for all the insights.

    -AJ

  52. I have been in the Car biz since ’03 and have done everything except turn a wrench. I feel like a robot going to work, I have no enthusiasm for my job so the change I want to make is to get out of the car business and work for myself. I enjoy great coffee and recently I started roasting it at home. I have found a passion for coffee how it goes from the shrub to your cup. I find it very interesting how you can manipulate the taste by adjusting the heat, time, and origin of the bean. I have started selling coffee but to only friends and coworkers. I would love the help and push to make it a full time business.

    The risk involved in this move I feel is huge because I am the sole provider. I am a husband and father of two. My decisions just don’t effect me. My biggest fear is the inability to feed and provide for my family.

  53. Hoping it’s before PST 5pm! (nearly midnight over here), but was just forwarded your article by a friend so thought I’d contribute.

    The risk I’m currently going through is leaving my secure, safe, slightly boring but well paid and rewarded job, and starting up my own Acai distribution business. I worked very hard to get the job, and love the company. Risky? Sure, I’m 22 with limited experience, and never worked in a start-up before. I have very limited savings to start up the company, and have no clue of food production or distribution. If it goes to pot, it may be difficult to get another job as it looks like I’ve bunked out of a very desirable 3 year graduate trainee job, after 9 months. The reality is that I’ve seen a massive opportunity, and starting up my own business is what I’ve always dreamt of. I’m not learning anything in my current job any more, and would learn bucket loads starting up by myself!

    I’m, leaving my current job 31st August, therefore have to get the Acai business to a certain level prior to that!

    1. Go for it Charlie! One thing to think about, is that you can work full time on your job while working part time on your fortune(Acai) You can have the best of both worlds! I learned this from Jim Rohn years ago…. It has served me greatly.

  54. A week too late but felt compelled to share. My name is Kenton Taylor, I’m 26, Director of Sales. High school Valedicotrian, dual sport college athlete, climber of the corporate ladder faster than the average bear, and officially MONEY TRAPPED. If reading could translate into action, I’d depart from the 9-5 drudgery, and embrace my passion (sports or fashion). I read all the books, blogs, and it took the “FLYING BIRD SUIT” special on 60 minutes to awaken me from my corporate coma. The Bird Man (base jumps and flies) said “People think I’m crazy, I think waking up at 6, sitting in traffic, and sitting behind a desk all day is crazy”

    I want to take a risk. I want to build something on my own. One month ago, I made 2 personal goals: 1. Increase my Spanish proficiency (Duolingo thank you) 2. Start a venture, any venture, but a profit generating venture. The writing down of my personal goal to “start a venture, any venture” is a microcosm of what my biggest hurdle has been to date. Ambiguous. What’s my passion? What do I want to do? First it was open a Crossfit gym, then it was underwear/undershirt line, digital signage, personal shopper, sales consultant using golf as the “bit or delivery method”, sports travel consultant, you name it I’ve considered it but risk of the unknown vs. risk of opportunity won out.

    The risk short term=loss of startup costs, time, failure.

    The risk long term=abandoning a steady, consistent career, for a risky, pivot of passion.

    I’m a perpetual learner, experiencer, sharer, and I want a job/career where those aren’t wishes but constants.

  55. My life-story thus far is not of too much ups-and-downs. After my Masters I consciously made a decision to work for small companies. I wanted to be part of a company where contributions made difference. Where one gets opportunity to get involved in every aspects of company development. After 10 years following that path, I decided that it was time for me to look at the other side of the pond and work for big companies and see what issues are faced by the teams there e.g. why are big companies slow to react to change etc. And I got an opportunity. 5 years ago Symbian sponsored me to move to UK. It was a big risk. I had never worked on Symbian platform and had never worked for a big company and that too in a different country. And the “fun” started from day one after joining the company! It was amusing time for me to see that commonsense is not a common thing. Then I joined Intel to understand and experience working with an even bigger company. It has been mostly smooth sailing in my life. But I was missing something. I was missing the action, the passion and the outright ingenuity with the way small companies work. Hence few months back I took a plunge and decided to go solo and do something of my own. After all now I know how both small and big companies worked! So, after 15 years in tech-industry working on software engineering on many fantastic projects, I decided to do what I actually want to do and be master of my own destiny. This is the first time I am venturing into entrepreneurship. Its like that feeling when you sit for the first time on a bicycle and try to ride it. You are nervous and even scared that you may fall, hurt yourself. But then you gather all the courage you can and make that great leap of faith and finally put pressure on the pedal and ride. You fall, you are hurt, you bruise your knees, but you don’t give up (well, I am talking about the kids of my generation who had to learn riding a bicycle without the supporting wheel you see on today’s kids bicycle). Ultimately you learn to ride the bicycle and it becomes second nature to you. You do not fear riding the bicycle again! I am now like that small kid who is sitting on the bicycle for the first time and ready to pedal. It is the same feeling!

    My motivation to leave my well-paying secure job was to not have to regret, later in my life, to not have done what I wanted to do. Before I leave this planet, I want to disrupt at least one industry. That is my dream.

    It has not been easy for me to break the mental mold of “try to have a stable secure job” that was so firmly fixated on me by my surroundings since my childhood. It was always ingrained on me by the elderly in my family that business is not our cup of tea, if one fails in business then thats it, its the end and the person is ruined for the rest of the life! To some extent that was, probably still is, true in the land from where I come. My country of birth (India) then did not have a better support system for entrepreneurship. Once you fail in your effort at building a business, you are stamped as a failure and that sticks to you for the remainder of your life! I understand why my parents fret when they hear of anyone becoming an entrepreneur. They have seen almost three attempts within my family to start a business. Out of those, two failed (one in a very dire misery) and only one managed to pull through (not with an astounding success, but it has not failed either). The one that ended in dire misery was my grandfather’s transport business and it was long time back i.e. after India got independence in 1947. And it was not due to my grandfather’s lack of experience or lack of funds or customers! In fact it was a successful business. It failed due to the policies of the government. India, by constitution, is a socialist country. After gaining independence the government started grabbing private land, started controlling businesses. My grandfather lost both his agriculture land and his business. During that time there were no grievance redressal mechanism in the country. The country had just got independence and there was general euphoria and opinion that the government knows best. A well-to-do-family immediately went into bankruptcy. My grandfather, once a businessman employing people, went on to struggle to even feed his family! What would have been the state of mind of a person in that situation? I don’t know, but I was told that he drank himself to death. My father was eleven years old when my grandfather died. With the death of the sole bread earner in the family, the situation just spiraled down hill. My grandmother, a single mother then, bought up my father and his three brothers. Human beings have survival instincts. They come up with novel ways to survive. My grandmother similarly came up with a novel way to help her kids beat hunger. They use to drink lots of water during the day whenever that felt hungry. And at night, so the kids don’t wake up due to hunger, my grandmother fed them rice flakes with lots of water. The effect of mixing rice flakes with water is that they expand and you feel full even with eating just a small amount! That helped the kids sleep calmly at night. The only “delicious” food they use to eat was during Diwali festival, and that was one boiled potato per kid. If they were lucky, they use to get a meal once a year from a nearby temple. They also survived by using clothes thrown away by their neighbours and relatives. These were the kids who went to school with torn clothes and no foot-wear(even today when I see my father’s feet I see the mangled toe-nails he has because of the injuries inflected due to walking bare-feet during his childhood). Imagine the impact this would have had on the young mind of an eleven year old boy! My father was a very bright kid, winning newspaper math competitions, was good at science subjects and created a electro-mechanical device (Actually, when I was a kid, I worked with my father to build a moped for his boss’s daughter! He is a DIY guy). He struggled a lot with English as a subject though. He has worked very hard to build a stable life, starting from going door-to-door as a malaria-medicine delivery government employee to an “promoted” aeronautical engineer in semi-government company. But even then our financial situation had not improved much. I remember when I was doing my Masters in Computer Science, my yearly college fees was 50K rupees where as my father’s yearly salary was 48K rupees. We couldn’t even afford more than 250ml of milk each day! (But my mother use to give me 10 rupees almost everyday so that I could pay to a family in the neighbourhood to use their computer for one hour). But every decision my father makes, even today – he is 70 now, is rooted in those painful events of his childhood. He has become risk-averse. He fears that if we fail again then it will be unbearable. And I have been bought up since childhood with stories such as these and similar business failures. Imagine the mental leap I had to make when I decided to start on the journey of entrepreneurship. And imagine the reaction from my family when I informed them about this! Every weekend when I talk to my parents over Skype, the questions start pouring in: “So, did you find a job?”, “Did you start making any money yet?”, “What about your future?”, or the punchlines such as: “It is not good to be without a stable job.”, “The neighbour’s son was just sent to UK by his employer for a project”. And on top of that, I keep receiving emails from recruitment agencies regarding jobs at big-shot tech companies. Very tempting. But I am holding onto my decision, risky as it may seem. I have just started packing for the journey ahead. I know the journey is going to be exciting and there will be some tears on the way. But I am determined to complete it. And I shall succeed. And indeed I will.

    BTW, the second business that failed in my family was started by my uncle (my father’s elder brother). He wanted to resurrect the transport business of his father. He wanted to show to the family that we can still do it. But he had to do some mental preparation himself. He first made enough provisions for his wife and kids before jumping into doing a business. He did not want the history to be repeated. For that he had to take a job. Work hard and have decent savings in case things don’t go as planned. But as you can imagine because of this he was able to start the business very late in his life. His expectation was, his two sons will join him and carry the business forward. Everything started as planned. They initially started with just one truck. Went on to lease another one in few years time. Both father and his two sons worked together. The father and the younger son used one truck, the other truck was used by the elder son and one employee that they hired. Business was chugging along, it was not very good but it was not terrible either. And then a big multinational announced a major electricity generation project in their city. They required lots of logistical support. My uncle saw an opportunity and put his two trucks into business at the multinational. Things started really going well. In fact, they had to lease few more trucks and employ people. They took loans from bank to support the growth. Even my father chipped in some money for the garage for the trucks. The business went very well for few years. My uncle was able to regularly pay his loan installments. And then fate struck (I usually don’t like to use the word fate because it attempts to put the blame on someone else – an unknown entity!). The multinational wound-up its operations. The whole city and the surrounding towns and villages that came to depend on this company started scrambling for survival. The multinational’s name was Enron. Globalisation is a double-edged sword. As it can build prosperity across the globe, it can have negative impact on a remote corner of the world due to some fallacies in other part of the world. My uncle tried frantically to survive the business, redeployed his trucks even in challenging conditions across the country. But things did not pickup. Both his sons gave up on the business few years from then. But my uncle couldn’t. He laid-off all the employees, repaid all the bank loans (he did not default – it is seen by many as a sign of failure in India). He kept his first truck that he bought but sold everything else. Even at a very old age he drew the truck to keep the business “alive”. He died of heart-attack a few years later. His elder son now works for my sister and her husband’s company, the only business in my family that managed to survive. But not without its own ups and downs, such as effects of bird-flu and terrorist attack that affect the small businesses. But one thing I have noticed when I look at the history of my sister and her husband’s business, and that is, that they both have immediately pivoted as soon as possible whenever they realized that their business is not viable. So they went on from manufacturing and supplying toiletries for companies to supplying door-to-door groceries to households, to manufacturing hot-drink premix and operating travel agency. Today they have four businesses (not big but profitable), one is manufacturing premix, second is as organisers of leisure and educational tours for student and adults, third is supplying toiletries for corporations and fourth is exporting Alphonso mangoes and Indian spices. And to top all that, they employ people! They are the role model for me in my family.

  56. This post has perfect timing for me,

    My name is David, I’m 27 years old, have a MSc in Engineering and I’ve been working in quant finance over the last three years. I plan to do an international assignment and move to London in the next months.

    I work in financial risk management consultancy and I think risk management perfectly sums up what life is all about, and what you perfectly said in this post, it is essential to know how to measure risks in life (financial and non financial) and take the right decisions based on your criteria,

    Moving to London is going to be hard as it is the most competitive hard working place in finance, but I’m willing to take the risk, as you said learning at this point is much more important than conformity.

    Risk is not something to avoid, but something to learn from,

    I agree with everything you said and it gives me a lot of motivation to see that my thoughts are so close to successful people like you,

    Thanks for your post!

  57. (In Fonzie voice) Heyyyyy! My name’s Alex and I’m 25 and currently working independently as a web designer. To be honest, the work I’ve been doing recently (building sites for small business clients) is almost too easy and thus no longer very challenging or fun.

    My challenge: To create a passive income stream so that I can try to shift gears from the web design business (what I’m good at) to eventually owning a restaurant (my dream).

    In the next 30-60 days: I am thinking about accepting a position as a manager at an upscale Italian restaurant, shadowing the owner, who has expressed interest in me coming to apprentice under him to learn the intricacies of restaurant ownership/management. He told me he wants to spend less time at the restaurant and more time at home with his family, understandably so as he’s run the restaurant for some 10-15 years and had little time away from it. I haven’t given him my answer yet and fear if I wait too long, it will be off the table.

    The risk involved: I am worried that taking this job might mean less financial independence and less free time. Currently my work as an independent contractor has given me an ‘eat what I kill’ mentality and I’m reluctant to give it up as most jobs I’ve had getting a bi-monthly paycheck have just plain sucked and working for myself has been amazing and surprisingly motivating!

    As a side note here: one my favorite movies is Yes Man with Jim Carrey and I try to say yes to as many opportunities as I can, staying optimistic that even if I don’t realize the opportunity completely now, eventually it will all make sense.

    My past risks have included launching my first business (a non-profit medical marijuana dispensary) which did very well up until I felt like it was no longer a safe business to be in legally (federally at least). I also helped associates launch 4 similar businesses with my business plan that all were successful as well. With my departure from that industry I realized what I wanted most in life was to be financially independent from a job and find something that didn’t seem like work. My first thought was a restaurant/bar, knowing fully well that they are THE most risky business to get involved in.

    I’m trying to figure out how to make the move from web designer with entrepreneurial experience in the MMJ industry to a restauranteur. I’ve worked as a host, bus-boy, server, bartender, and pretty much every position except cook (Can’t wait for Tim’s new book The 4-Hour Chef!) and manager, so this isn’t completely uncharted territory.

    I also love to travel and have thought alot about volunteering in Africa or South America, but haven’t found a cause I’ve really resonated with yet besides maybe OLPC (one laptop per child).

    Any help from you guys (Ben and Reid) would be greatly appreciated. Tim, you’re like a guru to me and I would be over the moon to get a reply from you even if I didn’t win the contest!

  58. This blog post resonated with me for two reasons; 1) I just exited an eight-month period of (unexpected career) change, and 2) my new job at Tallwave, a venture accelerator making a name for itself in Arizona, is one where I live in constant change.

    I decided to illustrate my story by posting the blog entry I wrote the night before my first day. I cite a lot from the Tao de Ching, a Chinese text that resonated with me in college so much that I got a tattoo of the characters. It is a text that speaks to constant change and the necessity of embracing it.

    —————————

    “Taoism”

    So here I am, the night before my first ‘real’ job, sitting restless & sleepless at my desk with a glass of scotch.

    I promised myself I’d write some sort of journal entry encapsulating the past eight months of…self-discovery…before I started at Tallwave. Yet I honestly don’t know where to begin. That is, until I heard two songs on 104.7 today.

    I guess we can start with Katy Perry’s “Part of Me,” which best sums up my surprise when I got back from prancing around Europe for a month only to find out that the job I had lined up (and was in negotiations for the entire 12 months prior to college graduation) was no longer there…

    I’ll stop myself there.

    So it was back to the restaurant to pay rent, later picking up a job at a gay bar, working both for a while, then cutting down to just the bar. All my free waking hours were spent clawing at any and all personal connections, job leads, applications, cover letters, interviews, meetings, and pots of coffee.

    Two utterly painful realizations at this point: 1) when you think you’ve been working hard, (newsflash) you don’t know the meaning of working hard (to the point that in hindsight, it’s almost laughable), and 2) like a game of chess, unless you are on top/ahead/& everything in between of your sh*t, you’re gonna get a big kick in the pants. Trust me, it’s coming. The world takes no prisoners.

    Three times I got really, really close. This led to realization #3 and #3.5: for each application, the ensuing process is drawn out (and companies are nowhere near as in a hurry as you), and the phone call you think is going to be an offer the day after you rocked your final interview is probably either a rejection or news that the company suddenly decided they need to be downsizing instead of hiring.

    Like the initial surprise, all these (except for the Red Bull opportunity) were probably blessings in disguise; however, at this point, my levels of discouragement and sleep deprivation were reaching critical mass. Not to mention the utter satisfaction from the absolutely wonderful clientele I had the pleasure of dealing with at the bar.

    Solution? (Per realization #1) Work harder.

    And harder I worked. I gave Archer’s rampage a run for its money. I was livid. I had a bone to pick with the world and I let it know. Global warming? Yeah, that was my fault, sorry…from when my head spontaneously combusted & flames shot out of it. Really, this rampage should have been named. Like when they give names to hurricanes.

    More pots of coffee, less sleep, lots of frustration and a few months later, I got a phone call. I remember it quite clearly. I was ‘out for a stroll,’ walking down Camelback Road, passing the W. ”We’d like to offer you the job.” At this point I was so numb it didn’t register. Really, it was my preemptive realization of lesson #4 that caused this.

    “I accept.”

    “Great, we’ll have the contract forwarded by Monday.”

    Lesson #4?…coming full circle to my ‘welcome back to the US present/surprise’….Don’t stop until something is signed. Monday it set in.

    Returning to the songs I’m using to help me try and convey all that I learned the past 8 months, the second is “What Doesn’t Kill You” by Kelly Clarkson. No, my song choices were not influenced by the music selection at the gay bar. I actually hate Katy Perry. But her song is too perfect for this story.

    On the other hand I do, actually, have a soft spot for Kelly. And quite frankly, her song sums up all the feelings, lessons, and occurrences I either can’t put into words or don’t want to go into detail about…which is ironic because said song was performed by a drag queen one night while I was working at the bar. The things I won’t miss…

    I have stories for days from working at the gay bar. I have a newfound confidence that I can handle anything (really, anything) that’s tossed at me. I hit rock bottom emotionally & financially. But I picked myself up & kept going. I learned when/how to ask for help & how to accept it. And finally, after doing the ‘right things’ for so long, an offer came.

    I myself am still trying to wrap my head around all the occurrences and lessons from the past eight months…which is why it may finally be time for that Tao tattoo:

    “The Way that can be experienced is not true;

    The world that can be constructed is not true.

    The Way manifests all that happens and may happen;

    The world represents all that exists and may exist.

    To experience without intention is to sense the world;

    To experience with intention is to anticipate the world.

    These two experiences are indistinguishable;

    Their construction differs but their effect is the same.

    Beyond the gate of experience flows the Way,

    Which is ever greater and more subtle than the world.”

    Call it the year of the dragon (I’m an ‘88 baby), but 2012 is really falling into place. Landed a great job my peer should be jealous of, met someone I see myself spending the rest of my life with…now just have to get rid of my ridiculously slow car & everything will be peachy.

    “The Way is without form or quality,

    But expresses all forms and qualities;

    The Way is hidden and implicate,

    But expresses all of nature;

    The Way is unchanging,

    But expresses all motion.”

    ———————————–

    So to answer the question, I’m not thinking about making a change to my career in the next 60-90 days. Why? Because as a result of the changes I made and underwent to be in this position, I’m smothered in change everyday. Like the Tao, I am one with change.

    It’s scary.

    It’s risky.

    It’s unstable.

    I have no clue what I’m doing. Everyday.

    But I’m learning a lot.

    Coming back from my graduation trip to find out my job wasn’t there anymore? Having to werk it at a gay bar to survive, after graduating with dual business degrees with honors? My new job that, in a nutshell, is change incarnate?

    Make me resilient.

    Come at me, bro.

  59. Great piece and good writing Ben and Reid.  

    In short, my comment is about  breaking away from the certainty of a career in law and, by offering FREE labor, get a high level assistantship with a tech or marketing company.

     

    When I think of risk, I think of when man first discovered fire. What was that like? What was it like approaching it? Something so frightful and dangerous. Fear of taking risks is like that fire: small and managable can give warmth and help you posper, yet once too big, can paralyze you from concern of getting too close, or if too close, burn you to death. 

     

    Starting this comment with fire is my risky “choice” to embrace that fire, to risk, get noticed and matter, or blend in and die irrelevant. The choice is in all of us. Except that in this brand new world of ours, as The Startup of You suggests, taking risks is a choice no more. It’s a necessity. A necessity stemming from the need to stand out, to push past the crowd, the business as usual, the 9 to 5 for 9 to 5’s sake, to be part of this tribe of early adopters, to dare to be different. It’s a necessity because in a flat world of ever decreasing entry barriers, anyone can be the same. It’s a necessity because this flat, unbound world is not much different from a blog article like Ben and Reid’s, with a sea of comments, where all you see is the sea and not the individual water-like comment molecules that make it.

    In essence, what The Startup of You suggests is that while taking a risk with one’s career will not eliminate risk itself (after all, it’s systemic), it might just be the best insurance from irrelevance, because deep down, we want our existence and our life product to matter. The most fundamental question you can ask about anyone or anything under the Sun (be it an action, event, product, business, non-profit, person, idea or risk) is: does it (s/he) matter? The Startup of You helps so that you may answer that question for your own life with a resounding YES.

     

    Here is how I want to matter, what I want from you Ben and Reid, and what I’m willing to do for it:

     

    I want an in-house assistantship with a high-level entrepreneur, preferably in a tech or marketing company. And, Ben and Reid, since you are trying to help me, the least I can do is make it as effortless as I can for you to reach your goal. While I realize there is no such thing as a free lunch, I can get as close to it as possible by working for free, working a lot, while requiring virtually nothing.

    I will work for free. I have 14,916 dollars and 58 cents saved in the bank and will work for free for as long as that money will last (and trust me, I can make it last). Getting paid would be great, but I’m not planning on it, as experiential knowledge and having the chance to learn from a great mentor is infinitely more important. 

    I will work a lot. While the proverbial “nothing was handed down to me” applies, examples might prove more helpful. First, because my parents could not afford to send me to college, i worked full-time while going to school full-time, graduating debt free. Also, 60 hour weeks were a common occurence building a Wall St trading firm, but just as common were the 100 hr weeks during its last dying breaths in the peak of the Great Recession.

     

    I don’t need much. Phrases like “company perks” and “during business hours” don’t apply to me for I am hungry and I am humble. I don’t need a company computer, personal office, fancy title, job description or relocation package. I will do what needs to be done, and if that means having to clean the floor, I will do that too. 

    Finally, I dont need to be babysat. Having sat on both sides of the hiring table, I deeply understand the management-employee relationship, what it means to “own a problem,” and believe that a good attitude is at the center of the work universe. 

     

    What I am giving up?

     

    The two main risks we take seem to be either to survive or thrive. One grows out of scarcity thinking and the necessity to meet our immediate needs – e.g. old company downsized so now one searches for a new job, even in a different industry. This type of risk is no risk at all because the alternative (the jobless status quo) sucks. Thriving, deliberate risk is true risk, not born of necessity and as you note, innitially appearing as a worse alternative to the comfort of the current status quo. I’d like to think the risk I’m taking is a deliberate one. 

    I just graduated from law school and have a good law job lined up. In short, by taking the above proposed “risky” path, I risk forgoing and likely “will” forgo financial safety, prestige, giving up the savings I have accumulated, leaving behind the certainty and comfort of the environment and people I have known, or just looking foolish in general. I also have a big fear of screwing up and making both you Ben and Reid look bad for recommending me (I have yet to make a recommender look bad, but maybe it’s because I am so afraid of it 🙂

    While, by living the comfort of law, I will risk a lot of external, safety oriented things, what I will not risk is what drew me to law in the first place, the ability to analyze problems and manage the risk in each. 

    When I think of lawyers, I think of risk management machines, looking at the downside, costs and flaws, always analyzing them more than any potential benefits. Just as the sole function of a speed governor in a car is not to let you go past that speed of no return, it is the job of a lawyer to manage and calculate risk for a living. As a side note, as i started to write this comment, my risk governor kicked in, calculating the risks of writing this comment and the trade-off between the highly uncertain rewards of winning a contest and the dead sure sunk costs of lost time. I actively had to shut up the lizzard brain that was whispering “shouldn’t you be studying for the bar”? 

    In closing, through this assistantship, I want to go on to change the world, leave my mark on it while bettering the lives of those around me. However, if my free work can as much as get that entrepreneur mentor I may have the chance to work with to spend five less minutes at the office and five more minutes with family while leaving me richer in friends and know-how, I would have changed the world already. 

    Best, 

    Orge

  60. Hi Ben and Reid,

    Thanks for the great post; I will definitely be rereading this throughout my career path. I am a 22 year-old mechanical engineer who has been working in the Michigan automotive industry for just under a year now. As comfortable and well-paying as my job is, I’m not inspired at all an have actively been looking to stir things up and start living the life I know I’m capable of.

    Within the next 60 days (at the latest) I plan to change jobs. As easy as it would be to stay in engineering, make a great living, retire, and settle down, the thought of that stuff creates the most boring life I can think of. My real passion is shoes and yes guys can love shoes too. I want to take my love for design work and creativity into something I’m truly passionate about: crafting shoes that are stylish, extremely comfortable, and anatomically healthy.

    Boy is this change risky. Not only could my creations not sell but also I would be giving up a stable career that is helping pay off my massive debt in the form of student loans. The tough part too is figuring out how to even start; do I study at a shoe design school in Italy? Is it possible to convince Soft Star Shoes to take a shot on me for an internship? Could I somehow get trained by Roberto Ugolini and become his mentor?

    I love my family and friends but like the rest of the world, they lead comfortable lives without big risks. That is why it would be amazing to talk to you both about this career move to truly know what I’m in for and get your opinions on how to best follow my passions and achieve my potential in life.

    Thanks very much for reading this and offering such an invaluable prize to your winner.

    Your future shoemaker,

    Brian

  61. I want to realize the dream that I have had pretty much for the last 10 years: To start a company doing something original that I can be proud of and which excites me, something which will allow me to create jobs and financial freedom for myself and my family.

    Since (finally) resigning from the corporate world, most recently in a well paying executive level position that was 70% travels in an industry I had no passion for, I realized that it is now or never, and doing instead of thinking was the answer.

    Calculate your worst case and have a plan-b so that the worst case does not happen. For us it would be running out of money, and so we have a set timeline for when I would need to go back into the job market.

    Beyond covering the worst case scenario base, ask yourself these four questions to ensure you take the right calculated risk:

    – How significant is the potential outcome?

    – What is the likelihood of success?

    – Can I find the resources required to make this happen?

    – How aligned is it with my long term goal?

    The worst thing that can happen now is that you are one step closer to your end goal. “Try to fail, but do not fail to try.”; Khosla

  62. The Start-Up of Me – based on a true story

    ***Prologue***

    I am currently 25, living in the bustling metropolis of Singapore. Since young, harnessing creative ideas to build and lead new things from scratch gave me sublime pleasure. However, growing up in a highly competitive and structured society, I soon found life and choices being steered more by conformity than my passions. Fortunately, an epiphany I had last year rekindled my inner truth, and ignited a fervent desire to abandon this mind prison so many of us are trapped in; and begin the pursuit of what truly drives me.

    ***Chapter One – The Biggest Risk and Leap of Faith I Took***

    I took the biggest risk of my life last year. I was a 3rd year university law undergraduate studying feverishly for exams when it suddenly hit me. Is being a top career lawyer or banker where I saw myself being happy in the next 5 years? The answer was a resounding, no.

    I realized that obsession with material wealth in itself, wasn’t the answer to true happiness and fulfillment. Only by doing something that you truly loved would bring this out.

    After some deep introspection, I realized that my hobbies and past-times were actually more indicative of the real person I aspired to be. Of particular importance was the fact that my most recent hobby projects, building 2 private and tight-knit online social networks (for movies and music), had been very successful and gave me intense satisfaction.

    And I did all this without any technical background or skillsets. I simply had an idea, a vision, and I went in search of organizing a crew of people who had what I lacked to make it a reality.

    I immediately saw the similarities of creating and managing these projects had, to the current ecosystem of internet startups. I essentially just had to apply the same lessons, experiences and skills I had used in these projects, and expand them towards building up my own web startup.

    Right there and then, I made a decision to leave law school in pursuit of my true calling.

    ***Chapter Two – The Direction in 30 and 60 days***

    Having developed the main concepts, features and design interface, the final critical element I am in need of now is a trusted web programmer for a co-founder, not just an employee.

    Therefore, what I want in the next 30 days is to find a suitable candidate, and for the next 60 days, come out with a working prototype.

    Risk 1 – I am afraid I will not be able to find a tech co-founder I am able to trust and share all my ideas with.

    Risk 2 – I am afraid that any prototype release might not have all the key features I would like, and potential investors might not see the true potential of the project.

    Solution 1 – I realize that any partnership, especially of this magnitude, requires trust and a leap of faith. I think I can minimize risk by taking little bets on potential candidates, perhaps by asking them to test-build some small features first, and monitor their competency and the chemistry of our working relationship. I also need get out of my comfort zone to network more to be exposed to more new candidates I haven’t met.

    Solution 2 – I need to realize that the prototype is meant to be a simple and concise of what the main purpose and objective of the startup is about. I also need to fight my constant urge for “perfectionism”. The focus should be connecting the message to prospective investors clearly and in a manner that they can understand and appreciate. The more complex the product is, the less likely someone is going to understand it. This acts as a motivation to cut out all the clutter.

    ***Chapter 3 – ***

    This part is still unwritten. I am hoping I will get an opportunity to add Ben and Reid to this chapter and my story.

    Thank you for your time and consideration.

    P.S. I really love your blog and books Tim!

  63. Great post!

    I have been working in the financial services industry for the past 4 years and my current role as an investment associate is not fulfilling.

    I am very interested in e-marketing and would like transition into a career in the digital marketing industry.

    Working in high paced and always changing environment, I have learned to be adaptable, open-minded, and a fast learner.

    I work in an industry that is filled with all sorts of risks, so I have no problem taking risks. I just need to know where to start.

  64. Gents, thank you for collaborating on this post. I look forward to reading the book. As a Career Advisor my contribution to the world is to help others to make work a positive aspect of their lives.

    It’s been interesting reading through the comments, thanks to everyone for being willing to reveal these dilemmas, concerns & as many people acknowledged, fears. I will go through them from the top and if its okay with you, try to reach out to a few people that have expressed they are willing to receive help from other readers.

    Given my role you would assume I would be able to manage my own career and give my own career the guidance I provide to others. This is partly true and as a result of my insights into Career Development I have been able to acquire a full time position which I absolutely love to bits. The reality is though that we all find it difficult to see ‘the forest from the trees’ in relation to our own careers/lives (the two are inseparable – part of the same whole). So, with that being the state of play I have backflipped on not entering to allow others the opportunity and instead reach out to ask that you please consider ‘helping a helper’.

    With my incredibly rewarding role working with a professional sporting team, I am spoilt on a daily basis. I have an incredible workplace & the individuals within are a privilege to serve. Each day I arrive with a smile of anticipation and leave with a wonderful sense of contribution.

    So what is the career dilemma you might ask? It’s that the position is so good, it holds me back from going after my dream to live & work in Singapore & Canada. It’s so rewarding that even though I know that these other things would be incredible, the uncertainty that they may be less rewarding creates a gap I am yet to cross.

    Gents, I’m grateful for you allocating the time to write this post and consider the comments. I would really appreciate the guidance you could provide so will be keeping my fingers crossed for the announcement. Hope all is well on your side of the world, thanks heaps, Gav..

  65. As an international student in the United States, I face unique challenges. I cannot start a company in the US, or work part time or even freelance. I can’t expect to make money or be rewarded in material form for anything I do to challenge myself. Thus the normal motivations do not apply to be.

    However that does not stop me exposing myself to challenges and learning the most I can. My life purpose right now is to improve myself and be the best I can be. As a graduate student in one of the nation’s best computer science programs I come into contact with brilliant scientists and engineers and their ideas all the time. I’m using this opportunity to learn the most I can. Not only am I learning challenging new techniques and tools I’m also getting a birds-eye view of the challenges facing our industry and the world at large. In addition to the formal education I’m receiving I’m training myself to get better at meeting and talking to people and coming up with innovative solutions to problems.

    The changes I plan to make are mostly in the form of focus: I already focus on pragmatic problems — not purely academic or theoretical ones. However I want to train myself at being better at implementing real world solutions. At the same time I want to get more involved in the real world community. I plan on releasing one new open source project a week. However, I won’t be making social media widgets or simple webapps — I plan on releasing core infrastructure components that others can deploy in their own systems. (One of the perks of being in graduate school is having ready access to infrastructure to test my ideas)

    This will have three benefits: give me more practice in implementing systems, give me a better idea of what problems need solving and how to go about it and finally help me establish a track record of building real software.

    The risk is that I will have to devote considerable amounts of time above and beyond my research duties (since I don’t plan on letting them slide). There’s also a chance that I’ll be waste a good deal of time on the wrong kinds of project. However, to tell the truth, it is a win-win situation. No matter what I do, I will gain practice in becoming a better programmer and technical thinker and I will produce software that others might find useful. Besides, I’m not getting younger. The time will pass anyway and I might as well spend it working hard.

  66. Tim, Ben and Reid … thank you for sharing such wonderfully written and thought-provoking piece. It absolutely resonated with me for reasons you will see below. Your generous prize to share your time and provide exposure through Linkedin is only one important part of why I am responding. To be honest, writing this post, is part of my journey/strategy and something on my “to do list” as I explore and pursue my passions.

    This is my first post (ever). I am on no social media, am a high introvert (not to be confused with being shy), and extremely guarded about my privacy. Thirteen months ago (almost to the day), I walked away from a six figure salary and a successful career in the U.S. Intelligence Community. It is indisputably the most drastic personal or professional decision I had ever made.

    There was no single reason for that decision … heck, I was in one of those industries that Ben and Reid “deemed relatively safe and stable,” worked relatively great hours, made a very good salary, and had high level security clearance to boot. Rather, it was the cumulative effect of working in a large bureaucracy where change is essentially needed but slow to occur and the ability for large organizations to set and stick with meaningful strategic visions while holding everyone accountable, is perennially elusive.

    I will always be grateful and look fondly on the many wonderful professional experiences that I could not have gained any place else outside of that particular world. But, over a period of time, I became increasingly frustrated, feeling as if something were amiss, increasingly intellectually underwhelmed and uninspired. It was a rather difficult decision to leave a safe, and by all accounts, “great” job (with the U.S. and global economies in decline) without any plans to look for or accept another job. However, I knew that if I took a related job in my field, it would be a temporary fix as I would likely encounter the similar systemic issues elsewhere. I really wanted to take a complete step back to take stock of what I really wanted.

    My upbringing and personal philosophy has led me to live within my means and to avoid debt so I was fortunately in a position to do just that. None-the-less, I did have to make some changes. I moved from my luxury apartment building in Arlington VA to a small studio in DC and began to identify things that I have always wanted to do but never taken the time. I volunteered at a yoga studio in exchange for yoga classes, I explored many of the wonderful museums here in DC, and rediscovered the beauty of a neighborhood library, namely that I could read for free – though a librarian politely told me early on that there was a 50 book limit!!! I also do some free lance work where I put my core skill set to work evaluating and writing reports in a variety of fields.

    For me, stepping back and taking time off (without acceding to the conventional pressure of needing to do something if only for the sake of appearing “productive” or avoiding the dreaded resume gap) has allowed me to make an important internal shift. And, I know beyond a shadow of doubt that I would not have been able to make that profound a shift had I made incremental or small changes while still maintaining a job as I tend to commit fully to one thing at a time. Logically, there was no “good” reason to leave. Yet, there was a certain dissonance between living the relatively “safe,” structured, and comfortable life and the internal agitation I was feeling at my core. There was a part of me that yearned to have more “meaning” as I defined it, in my life and to get back to that “scrappy” nature that I knew I possessed.

    What I didn’t mention was that I moved to the United States after finishing High School in South America and worked my way through my undergraduate and graduate degrees. By all accounts, landing the job that I had, and receiving offers and opportunities from every major Agency in my field, was a rather spectacular feat. So, the “negativity bias” that Ben and Reid discussed had really kicked into high gear when I made my decision to take a plunge and walk away completely as opposed to simply getting my feet wet. Ben and Reid state, “Asking yourself whether you can tolerate the worst case scenario is a quick and dirty way to size up risk in situations where you don’t have much information or time.” I would add a slight twist to that. Traditionally, one might use that to analyze new or unknown situations or opportunities. However, it is equally applicable to ask yourself that very question of your known and present situation. What are the risks for maintaining the status quo and might those be worse than your envisioned worst case scenario?

    In the end, no matter how you get there, whether by incrementally and routinely trying new things to build up resilience to manage inevitable change, or, taking a massive plunge when necessary, you will undoubtedly become a stronger, more experienced, and flexible person. And, even if you decide to stay your current path and do nothing, let that too be a conscious choice as it will also have similar self-empowering effects. We get one life to live …

    What change do you want to make in your career in the next 30-60 days?

    Over the next 30-60 days, I plan to identify and secure a position in the career field of choice (still undecided). I am interested in writing and publishing non-fiction, likely in the “Personal Transformational” genre. I have just completed a Transformational Author course where I learned that publishing a book is very much about “marketing” and “platforms.” Since I have resisted social media, I am behind the curve on this and would need to start accounts on the various social media sites, to include LinkedIn. Still feeling a lot of discomfort around this but that is probably a great indication that I should be moving towards it. However, I could definitely use some help in this area. I would also like to identify places to publish short articles online and in print. I would also like to begin conceptualizing and building my own website. I am considering writing a book proposal, to include the first 10 pages of the manuscript, for a writing contest – deadline is less than 45 days. However, this will in large part depend on how successful I am at building my platform.

    In the event that I am not able to be gainfully employed in this field within this time frame, I would like to identify and secure a job for which I would be a good fit. I would work on my writing part time.

    How are you thinking about the risk involved in this move?

    As I contemplate my next career move, I confess I am somewhat conflicted. I have always had an affinity for public service and have an educational background in the profession I left. Doing something completely different takes me further away from that field and government. However, at this point, getting into the writing and publishing world is something that I have thought about for a while and I would be willing to take a low-paying/high-learning job for at least for a few months if it gets me closer to exploring this option. All in all, there is very little risk at this point for me to explore any field. Actually, the worst case scenario is to do nothing, continuing to overanalyze my options and feeling like no job is “ideal.”

    Thanks for reading!

  67. Tim,

    I thought I sent my post in earlier today but I just checked and it looks like it isn’t there. I am certain the error was on my end as I was having technical issues earlier. I resent it again a few minutes ago but it is now after the deadline. Hopefully it can still be considered for the contest, but if not, I understand. Totally my fault, sorry!

  68. Note to my son:

    I don’t know if you’ve looked at any of these 490+ posts… I know you’re real busy.

    It does seem that my post was deleted without comment and a follow-up post has vanished, as well. That doesn’t surprise or bother me much – it actually reinforces my perception of opportunities and relationships not being made available to older guys like me.

    And if you read through some of the other posts, you will start to see a lot of patterns that I can’t help but relate to some of what Lefsetz has been saying about would-be rock stars, songwriters and performers. In spite of all the good and important work that guys like Ferriss and Godin do, I think they are creating a huge bubble of high esteem highly motivated cocky and self-important entrepreneur wannabees.

    As Lefsetz has said, writing and recording a song is easier than ever – and designing and creating a smartphone app is easy, too. That doesn’t mean anyone is going to want to see it, use it, or buy it. So many of those posting whine about self-fulfillment, the “money chain” around their necks, the drudgery of their 9-5 job, and how they have been inspired by these guys to quit their job, travel Europe with a backpack and $20, and then return to L.A. to start a killer software company that will make them rich working four hours per week.

    For every Seth Godin and Tim Ferriss, there are 50,000 or more who think they can do what these guys do and expect to be just as successful. Heck, we do not NEED another Seth Godin – one of him is more than enough. Lefsetz and others have talked about putting in your 10,000 hours to become an “overnight” success in your field. The blog posters seem to think all it will take is their emotional commitment to doing it – after that, nothing can stop them. After reading several of these posts, I wanted to slap a few of them up side the head – I wish Godin or Ferriss would do so. I think it is irresponsible of these guys to motivate and inspire these people without including some reality in the mix.

    Could I have had a more lucrative career in music or journalism or later on in computers and technology? Sure – but I lacked direction and I wasn’t willing, able or ready to invest the 10,000 hours into the education and experience that would have been required. And I chose to raise a stable family and maintain a good marital relationship. These 490+ blog posters are ready to jump ship on their careers, their lives, and their relationships to follow some vague dream using Ferriss and Godin and others as their role models.

    Don’t get me wrong – Seth and Tim are heroes of mine. And I have always said one should follow their own drummer, chase their own dreams, and live a self-determined and self-actualized life. But without some perspective and a reality check, I suspect that a lot of these well-intentioned people will crash and burn and end up living in their parent’s basements for many years to come.

  69. I’m well past 30, have a disabled husband and a young child – I have no business taking risks in my life. I have responsibilities dammit! Oh well – here goes anyway!

    My risk taking started back in 2000 when I realized that newspapers were dying. I knew that I could probably eke out a living as a journalist at some paper – moving around if necessary until I retired but I didn’t want to be passed by the online world. So I took a leap of faith and started copywriting for an online company. Fast forward to last year when I was a marketing manager at a decent sized company making good money and good benefits – but going nowhere.

    I saw an opening on LinkedIn for a job that I was kind of qualified for – SEO strategist. I threw my hat in the ring thinking “yeah right there are probably at least 500 people competing for this job.” To my surprise they called me and within 5 days I had a job offer.

    Now for the biggest decision of my life. It was for less money, at a company less than 3 years old, working virtually, and I’ve never met anyone in person. The risks? That I’d never get paid, that the company would fold as soon as I got there, that in this economy I’d not get another job offer soon, that I wouldn’t be able to afford my husband’s healthcare and on and on and on went all the cons in my head.

    But then again – it could be a tremendous opportunity to learn – really really learn and become passionate about a job again.

    Fast forward 7 months. I accepted the job and feel really blessed and fortunate. These are the smartest people I’ve ever worked with in my life. I’ve never learned so much so fast. I love it. Is the money there? Not yet but I’m sure enjoying the ride!!!

  70. I am the underdog. I’ll explain that in a bit. About a year and a half ago I went to my doctor for a routine visit and my blood pressure was up a little high for his liking. He did a couple tests and instead of taking time to figure out the root of my problem he was quick to place me on drugs. These drugs made me feel like sh*t. At first I was angry at my doctor for not taking time to figure out what was wrong with me instead of taking the easy way out and prescribing a toxic relationship that was meant for the rest of my life. Then I realized that it truely isn’t his responsibility…it’s mine. So I dove into self education and experimenting with different methods to solve my health problem and not just cover it up. I made a checklist of possible causes of hypertension and started checking things off. And I am happy to say that it worked! But it’s a long up hill journey that I continue to make.

    To answer the question, I’m in the process of writing a self-help eBook on how to lower bp the natural way and using prescribed medications, meant to cover symptoms and not cure, as a last resort. This is a big change and I have to admit because I feel so strongly about this and will be putting my thoughts and my heart on my sleeve I’m fearful of the risks involved. I’m afraid of the possible backlash and comments because I know with whatever risk that you put out in the open for others to see that people will love you for it or they will hate you for it. But I believe that fear is good, that fear means that you can really feel alive. That’s the fear that you feel when you approach that girl at the bar that could be the life changing girl of your dreams. I wouldn’t change the opportunity to feel this fear for anything in the world. Embrace it.

    I will be going up against popular thought that I believe needs to change. Things are hidden by big companies that effect our health and we don’t even know it goes on. If I can open up just one persons eyes, if they agree with me or not, I’ll be happy that the awarness started and will hope that I will have sparked some self education. I’m going to be taking a risk by going up against blindly followed tradition and thats why I am the underdog.

  71. Fitting with risk taking – I have moved to weekly email updates as mentioned in Tim’s book…….I just came across the email that contained this contest – I am asking for an extension of time to qualify for this opportunity.

    First off I can relate to Ben’s story of growth by moving to a foreign country – My wife and I took our 4 kids (2 of them 4 years old) to Mexico to live for 4 months. This was during the heightened time of drug cartels having shoot outs at the boarders….our families and friends thought we were insane! to say the least. Anyway, there were several challenges we faced including losing our rental property and trying to figure out where we were going to go, sitting in a parking lot of a market in the middle of mexico with very little money, not speaking the language and having 4 kids and months worth of luggage to carry around…….Prior to this, we had just lost everything – My first business failed after 5 years, we lost our home – everything……we decided to stretch what we had left while living low cost in Mexico and to reset and get focused on whats the next move in life. I cant begin to expand on what this experience did for our ability to cope with disruption.

    I have a few other stories about overcoming adversity in life but so does everyone else and I’m sure that you guys are not looking for a sob story here.

    This article post captured my attention primarily for the mentorship aspect of it until I read the article.

    I am learning to embrace my talents and skills and I want to start putting them into better use.

    I just won my first open innovation challange providing a process solution improvement, and I am playing a more active role in submitting my ideas to other challanges faced by companies around the globe.

    I am currently building a company at the same time, similar to the risk Ben spoke about with joining the board at Paypal.

    I am embracing this gift and thirst for learning and expanding my knowledge in various areas of interest in an effort to develop a career where I work with companies, governments, and maybe even individuals to provide my ideas as a catalyst to innovation, optimization and just plain old doing things better.

    My vision is to create a multi-billion dollar brand of companies that each one of them provides greater value and benefits to our clients compared to anyone else in the market or indsutry…. I am heavily influenced by the book Blue Ocean Strategy and their theory on sustainable corporations (blue Oceans).

    At the moment I have roughly 50 ideas in a book for business ideas and innovations and licensable ideas….I am currently working on several of these ideas to bring to market.

    I’m seeking people who are like minded and whom I can share my ideas with – I am looking for these people who can work with me and take my ideas and help implement/execute on them.

    I’m seeking people who are aligned with what they are doing, people who are having fun and who are excited and eager. Those who want to create to change the world to do things better.

    If its meant to be I’ll hear from you guys and if not, theres alwasy another opportunity somewhere and I will be open to it.

    I wish you all the best in this mentorship endeavor – I see tremendous value in this kind of thing becasue most people hear that they should get a mentor but few know who to seek out, what to say when they do and how does one develop that type of relationship. You guys just made it super easy and thats awesome!

    All the best,

    Robert

  72. Hi Tim,

    Follow up – Did my original post show up before the deadline? Will it still be considered for the contest? Thanks!

  73. Simply put, I just want to be myself 24/7. I’m tired of being “at work Josh” and “not at work Josh.” Right now my time is 80/20 in favor of “at work Josh.”

    My goal is in the next 30-60 days is to concentrate on my muse and spend my energy on getting back to myself, who is creative, out going, challenging the status quo, and raising hell.

    Right now I’m living an Evernote fantasy life because everything in there is what I want to do. It’s time to be me before corporate America sunk its teeth in me.

    “The day before something is a breakthrough, it’s a crazy idea.” – Peter Diamandis

  74. My post unfortunately did not make the competition deadline, but I have to try because of my admiration for Reid Hoffman and my excitment for the opportunity to learn from both him and Ben Casnocha directly.

    Thank you both for your helpful career development insights and sharing personal examples underlying them.

    As people who imigrated to the States from Ethiopia, my parents felt a sharp difference in education and technology between these two countries. One of their approaches to teaching me the value of the opportunity to make a difference here was through providing me with articles from the NYTimes Technology section, the Economist, and any other resources available to them. From a young age, I learned so much about people like Bill Gates, Steve Jobs, and other technology leaders that were making a difference in people’s lives around the world and so early on I knew I wanted to be a part of making a similar contribution someday.

    As I’m twenty-five years young, I’ll focus only on my current career risk-taking experience.

    For my first job after college, I was hired as a consultant where I analyze entertainment, media, and gaming companies for the firm’s advisory service engagements. Through my two years in this role I learned about assessing capital investments within the entertainment industry, and though I’ve become very good at what I do I’m motivated to learn exact steps toward accomplishing my childhood dream of making a difference as a tech entrepreneur and investor.

    Here’s what I’ve done so far:

    First I tried to implement steps similar to what Reid did at Apple, which is identifying opportunities that build a foundation for what I want to do and then demonstrate my capability to perform that function to the right person.

    So for example, in thinking of how to round out my operations background with the specific skills I need in the future, I rationalized that experience with transaction events in technology, media, and telecommunications industry offers a great stepping stone. Over the past five months I’ve used LinkedIn to email hundreds of financial service professionals and was able to develop from the effort at least twenty relationships.

    Having done that, in networking skills, I’d consider myself a self-taught intermediate beginner because I learned the more I know, the more I don’t know. For instance, I’m confident when I reach out to anyone because one of my greatest strengths is my ability to ask good questions and learn from feedback, but where I have room for development is in figuring out how to get interviews through the relationships I build. I don’t know how to transition from the positive persistent person you’ve agreed to chat with about your experience for twenty minutes to someone you’ll help get interviews. I’m worried asking people directly for help is risky because I feel that could make them less responsive or worse, hurt the relationship. More specifically, I’d like to learn how to develop a relationship where asking for help feels comfortable.

    Finding a new opportunity outside of my company is challenging and finding the right opportunity outside of my company even more so.

    I see the risk as two-fold; how do I know I’m implementing the right strategy to achieve my desired outcome?; how much more time will I lose before I can achieve it?

    I believe Ben and Reid are offering a wonderful opportunity for the right person to make the most of their highly valuable knowledge and skills, so you can’t blame a guy for trying when he sees something he values.

    What I believe makes me a great candidate is that I know specifically what I want to do and with expert advice I’m confident I can achieve results much faster. In exchange, the best I can offer to Ben and Reid at this present time is a great LinkedIn story.

    Thanks for posting this once-in-a-lifetime opportunity on your site Tim – I hope I still have a shot here, otherwise I hope your blog audience found something they enjoyed from my comment.

    Best,

    Menny

  75. Hi Brad and Reid,

    I’m the quiet risk taker. Risks I took so far can seem pretty low key but I know how each one of them changed me, opened a door in me to a world I only guessed existed and some ‘mind spaces’ I didn’t know I had.

    I lived in three continent, inventing myself anew each time, while keeping some of the good stuff from before. I was born in Israel, lived in El Salvador, CA and now NJ. I was a teacher (took many unconventional risks there), a scrapbook artist with an online custom albums business I built myself; a community outreach person and a relocation agent. Some I did at the same time, all while volunteering and giving back to the community I live in.

    I would like to utilize my different skills and talents to earn a living, one that will make me happy, feel accomplished and be a good female role model to my daughter. I’m currently seeking for a job in the event planning/producing business and hope to be at my new desk by September 2012. I tried asking for a raise at my current place of employment, tried finding a new opportunity within my company as I like what I’m doing. Unfortunately it became clear that is not an option and I need to move on.

    The risk involved in this move includes building a whole new network (will be my 6th in 20 years – an opportunity to meet new exciting people!), getting out of my comfort zone, finding a worthwhile mentor in a company where I will be able to learn more, utilize my talents and experience something new.

    We have only one life, we should use it the best we can!

  76. All:

    These have been some amazing stories. We really appreciated them. Out of the more than 500 submissions, we picked the top three and want YOU to vote on who should win.

    Read the three finalists’ stories: http://www.thestartupofyou.com/4hww-mentorship-contest/

    And then vote here: http://lnkd.in/xP-vUB

    There were so many other compelling entries. Please join the LinkedIn Group to continue the conversation — feel free to re-post your story as a new discussion, and then tap collective wisdom of our networks (and share your wisdom with others).

    Let’s get started!

  77. Hey All,

    Just wanted to say congrats to the people who won this amazing opportunity!

    I have read your stories and they are great and inspiring and I wish you all the very best with this and any new ventures.

    Niall

  78. Wow,

    The comments on this post are just as inspiring as the post itself.

    I really believe in your risk reward philosphy. It’s too bad most of us are too complacent to do anything about it.

    Right now i’m on my 5th career break living in France with my husband and 3 kids. I teach other people how to take the leap, a career break to pursue their goals and dreams, both professional and personal while also travelling or living abroad long term.

    Looking forward to picking up a copy of the book..

    Thanks

    Annie Andre Chief adventure-ologist, mentor and strategist.

  79. Hi guys,

    My name is Gabriel Lee, and I am studying a double degree of law and business at University of Hong Kong.

    After reading Tim Ferriss’ 4-Hour Workweek, it has really given me the juice to brainstorm potential business product ideas. I have several product ideas relating to what I know and what I do. For example, I practice Ashtanga yoga, so I have an idea that might be able to help out Ashtanga yogis. Secondly, I use to have a serious case of eczema, which I have manage to keep at bay as a result of of a lot of personal experimentation, information, logic, intuition, and luck, so hopefully I will have an information book to help out people who want to heal naturally from eczema.

    My goal is to be self-sufficient financially, so I can liberate my parents and treat them to the nice things in life (although they can afford those things by themselves, it is always nicer when it comes from their son). As for how much risk I am taking, I do not think I am not taking much risk at all. If I apply the 80/20 Pareto rule and the Parkinson’s rule to my academics, that will free up so much time for entrepreneurial ventures, so to be honest, I do not have to give up anything for this!

    Anyway, thank you the great article, Ben Casnocha and Reid Hoffman. A very enjoyable read.

    Yours sincerely,

    Gabriel

  80. As i have read this article, I learned that being a risk taker is better than just be in the comfort zone. For it helps you in making decisions that can improve one’s self. Even if your decision fails, you can still improve yourself by learning from that experience.

    thank you for this good article.

  81. I just had very sad conversation with a friend from another department in the massive company where I work. Management decided that he is not up to snuff so he was demoted, pulled out of his office and placed into a cubicle, and ostracized. He is 40-something with three kids. He followed the path of the typical careerist, thinking that he would sign up with a large corporation and have the comfort and security of a long career and a nice pension. Little did he realize that the biggest risk was placing all of his eggs into one basket. Now, he’s scrambling to find a way to support his family. It was a painful reminder that my goal is to ensure that I control my future and my income stream. Anything less is too much risk.

  82. Hi! My name is Cole,

    3 years ago I read Tim’s book and since then have studied it pretty much front to back. I believe in the principles and helped many other people put them to use in their daily lives. My main focus in the last year has been to develop an idea I had 3 years ago and we just had a soft launch in February before Vday (yes, Valentines Day). Without any marketing and just some word of mouth marketing we have acquired 900 users and our product isnt even launched yet. I believe that the idea my partner and I have could easily turn into a career for both of us and many more but we are getting close to maxing out our very limited self raised budget. In order to keep costs at a minimum I have self taught myself graphic design and lived in a small apartment while working full time and pushing the site.This is all very wordy I know, but that is my present situation and my 30-60 day goal is to create an amazing product launch that ‘wows’ our current user base and generates traffic to get us to our 10,000 user base goal.

    Also, I am a sales guy, I sell spinal implants to Neurosurgeons and understand risk all too well. If this doesn’t pan out… then the next one will. Trial by fire!

  83. I just recently graduated from college (Cornell class of 2012) and am spending this final summer home in LA preparing myself (mentally and physically) to spend the next year or two in China working on an education startup. This article really resonates with me; I have had to encounter each opportunity/risk with the type of analysis you wrote of; and with the “yes” mentality. Though I will not be making much in terms of a salary next year (especially compared to many of my friends working in steady-income investment banking jobs) I know it will be a tremendous growth and learning opportunity for me. The reason I landed the job in the first place was in deciding to study abroad last semester in Beijing. That decision in itself proved to be quite difficult – being in a fraternity, I was afraid of all the things I would be “missing out on”, and of course, in an uncomfortable and foreign environment. But I took the chance, by a thin margin, to go, be bold and open to everything- culture, opportunity, etc. And by happenstance I met two entrepreneurs, one a fellow Cornellian (a Chinese native who was running an innovative new school (or learning center – that teaches the liberal arts – in Beijing) and Richard Robinson, a serial entrepreneur who came to speak in one of my classes. The connections I formed there have been invaluable, and in fact, Dr. Nie, who runs the school, asked me to join him in Beijing to help him grow his business after I graduate. It was a difficult decision, but after listening to Reid Hoffman’s Stanford speech, I decided that what I would be missing out on by turning down the offer would be far greater than seizing this seemingly risky opportunity. I am now very excited to work in China this fall, and am prepared to return there with an open mind to continue learning.

  84. Knowing it’s too late for the contest, I’m disappointed to have not seen this until tonight; a Friday night in after hot Thurs and long week of work far from over. To any who read, please comment with any ideas, links, thoughts, etc.

    —————-

    As a Board Certified Behavior Analyst, my MS degree is in the objective data-based observation, definition, and systematic science of implementing behavior change under (mostly) controlled settings. Basically, I help figure out what’s really going on objectively, and teach others how to do the same to eliminate bad behaviors and increase good behaviors! Problem is…within my field there is a separation between academic research and clinical work in the field. Neither side actively seeks to promote research beyond scholarly journals for fear of bastardizing the necessary controls of true research. Simply put, anybody can say anything with really lame & weak sources (if any at all) in articles for TIME, Good Parenting, or Cosmo, etc. As a result, that’s what most people read!! Mentalistic “feel-good” short-term therapies see limelight via Dr. Phil, SuperNanny, and Dr. Laura. While that’s better than nothing, often it’s largely invalid and not based on sustainable methods proven by solid research. (get off my high-horse already right? haha) I’m disappointed by my field for not sharing a wealth of knowledge to the masses. I fully admit I’m a part of it, but am seeking solutions and need a solid source of income to support committed time to this topic near & dear to me.

    One concern I see is that so many in my field are working in autism or developmental disabilities fields, where the safe “apply & interview” government funded well paying jobs are for post-grads!! Clearly this need is vastly important, so please don’t misinterpret but my worry is that my field is largely ignoring the other 97% of the population. I myself took on such work with 60k in student loans on my back!

    Fast forward to my life now, over 6 years out of grad-school having worked in group homes and facilities for the developmentally disabled (typically mental retardation and many other co-morbid disorders) in 2 states. A majority of those loans still haunt, and I’m in another job with no opportunity for advancement in pay or status. We have little to no control over the politics that control the big picture. In FL, budget cuts continue to plague our field including the care providers whom we work with. Despite our best efforts, MORALE is often as low as the pay for our direct care staff, managers, and case-workers, and co-workers. Sadly the best staff often leave for better pay in other fields even though they love working with our residents!

    I PROMISE this isn’t a bitch session, but I’m spelling out my NEED for a BETTER working life and I’m surely not alone here!! The mention of healthcare jobs by Reid above is spot on and struck a chord in me that clearly resonates in this post. Basically, my job seems safe in the short term with steady paychecks….for now!! By the traditional risk-averse philosophy, treading water careerwise seems the best case scenario since new challenges don’t present a way to pay the bills next week, yet they are increasingly pulling my mind and heart elsewhere.

    ——

    I’ve yet to make the “risky” jump into other avenues where my empirical skills and experience can be applied. My passion is in the need to do something with a potential for helping a vastly larger audience than a caseload of 20-30 residents and their staff. This need for an outcome that holds a larger potential for real change in helping others is equally inspiring and frustrating without a “safe” plan of action and knowledge of how to make it happen and make ends meet doing so!!

    ———

    Many ideas of entrepreneurial endeavors have been sparked and lay somewhat dormant, with recently stronger thoughts of app creation (Chad’s “App Empire”) and licensing (Stephen Key’s “One Simple Idea”). In the past I was active with the local inventor’s association before even hearing about 4HWW concepts a few years ago. The “safe” negative self-rules still surround me, but I find myself awake many nights reading sites and books like these!! (and smiling to myself while doing so)

    Note that I HAVE pursued a patent and don’t regret that time & money spent, even though the technology ended up being in the works by others (those portable speakers to listen to TVs of choice at sportsbars? yeah, I was 1 year too late with my provisional filed and full patent in the works). I now know much more about licensing and marketing ideas, although still I’m only a slightly less timid rookie with little financial room for error. One looming idea in mind is to re-brand and market a vitamin supplement for a specific use that has potential explosion written all over it (exciting?). It’s chemically & biologically valid, and proven successful over years of personal and associate testing. Best yet, the market seems primed! I simply have no experience making it a reality! (pick your Google Image choice of “facepalm” and apply here)

    Focus on one or two specific projects is where I’m planning to go. As Tim would put it, I need my “muse”, but one I’m passionate about. The above being one, freelance writing for periodicals being another, app creation, and starting a discussion board for Behavior Analysis are other ideas still! Mentors for each are needed – THAT MUCH is clear, both for strong field-specific advice & encouragement/accountability. Reid’s blog post really provides a great parallel to my situations in my current duties as well as other potential paths of interest and passion for me (and hopeful career ventures).

    The common denominator I see in all success stories is PASSION, but a clear plan and efficiency are also vital. A reasonable balance of time & financial stability is needed with a heavy dose of action. FOR NOW, I PROPOSE a late night Friday cheers to NOT continuing to tread water or to drown in “paralysis by analysis”, but to finding the best way to reach a shore of success by moving on a plan!!

    – Matt

  85. I see that the contest is over, but I would still like to leave some notes of my story over the past 13 months.

    Interned at JP Morgan Chase Investment Banking division. Absolutely hated it,and ended up studying abroad in Spain for my final year of college. Came back, and decided that instead of finding a job I would go out and start my own company. I ended up finding my own start up ‘Franklin’s Lab’ which helped aspiring entrepreneurs in the NYC area actually become entrepreneurs. After having worked with over 70 entrepreneurs my company basically failed.

    I pivoted my learning and am now looking to build an iphone app. I worked at the famous burger chain ‘Shake Shack’ for 11 months to support myself. Not an easy feat for someone who had just graduated with a B.S. in Economics.

    Through my time there, I helped an investor raised 5 million dollars for his fun, I became a Master Teacher on ‘Skillshare’ (http://www.skillshare.com/profile/Rafael-Balbi/2137344/endorsements) , and am now working for ‘Lean Startup Machine’ (www.leanstartupmachine.com) as their head in Brazil, Dubai, and Moscow.

    Many of these jobs were very low in pay but astronomically high in learning. I know stand 13 months later as well rounded and much more astute professional.

    Please follow me on twitter @rafaelbalbijr or find me on LinkedIn – Rafael Balbi

    -in the spirit of entrepreneuriship

    Rafael B

  86. Wondering if a winner has been chosen for this as yet?

    I’d love to read their specific entry, and follow their progress / interactions with Ben, Reid and Tim if they allow it.

    1. Chris; Hi, this is Cheryl Obermiller. If you would like to read my full post, just go to the posts made on June 15, and find mine at 1:30. (That seems to be the easiest way to locate specific posts.) I would love your thoughts on my experiences!

      My understanding is that, at some future date, Tim will make a post about the contest and that it will run for 2 weeks after his post. Ian, who is managing the contest for Ben, shared that information with me several days ago so it should be accurate.

      Whether I win or not, I am going to start doing some video blogging in the next week or so, which I hope you will follow. One of the really cool things I’ll be doing at the end of the month is taking a trip to Europe. I’ll be posting videos about our 2 week trip through Italy, and will be showcasing the most interesting sights and delicious foods, all while demonstrating my method for business owners to monitor their financial activity even when they are away from home. Running a business while sunbathing on the Italian Riviera is an ugly job, but someone has to do it! I’ll post information on this blog next week, if I can do it without breaking any rules or being labeled a spammer.

      I hope you’ll follow my business progress, whether I win the contest or not – it will be invaluable information for aspiring business people!

      Have a fabulous evening!

      Cheryl

  87. Damn!

    That was a great and motivational article. Being a fresh entrepreneur, I just can’t help but feel all the most motivated and yearning to expose myself some more so a to take so-called “risks”.

    Not oversestimating risks seems to be one of the main component to build yourself a great career and make the moves others won’t.

    I actualy used to listen a lot to what others would think or say about X before actually strating X and that got me into many deceptions. Therefore I tend today to do what I feel attracted to without asking others for their opinion on the matter.

    Thanks for sharing.

  88. – What change do you want to make in your career in the next 30-60 days? (e.g. Change jobs, ask for a raise, find a new opportunity within your company)

    Make a fun and good living without directly relying on my existing qualifications and CV. In fact, burning my accountancy qualification. I’ve already left the field but in my past two jobs (managing a theatre company and visual arts charity) I fell heavily back into relying on what I knew how to do.

    Find a way to genuinely explore what I might enjoy doing.

    – How are you thinking about the risk involved in this move?

    I’d like to remove the net without freaking out or freezing.

  89. Hi Tim and Ben,

    Great article.

    Well to start off, I have to say that I have been facing a challenging situation right now. I just graduated from my MBA and decided to move drop off my job offer and move to another city because of love. And here I am right now in another part of the world trying to figure out what to do with my life.

    The change I want to make in my life in the next 30-60 days, first find out something that inspires me and feel me with the same passion that took me to move here and second engage in a new job that will fullfill this passion and generate opportunitites to keep chasing whatever is that makes my heart pump every morning.

    I would love to talk to you guys and get some perspective about life and choices to come.

    Thanks

    V

  90. This is exactly what I needed to read. I’m a corporate accountant planning to jump ship in the next 6-12 months. I’m counting this as my “career risk.” Bon voyage.

    Cheers,

    Norm

  91. “The survey results say you like being outside. Perhaps you could become a gardener.” My Year 10 guidance counsellor was trying to give me career advice. I smothered a laugh. Plants cringe in fear when I approach.

    “Well you are Dux of the school and with a score like that you should become a lawyer or doctor.” At the end of high school thousands of students choose a career based purely on their results.

    “No thanks,” I said and walked out of the teachers office. I didn’t want to be a specialist, locked into a career for life, I wanted to be a generalist.

    “Why do you want to work for a bank?” the interviewer asked.

    “Money makes the world go round,” I said. “And banks are in the middle of it. I want to learn how the system works.”

    “And why strategy?”

    “Once you know how the system works, then you can make it work for you.”

    That’s where I am currently – working in the strategy team at a major Australian bank. I am also an elite beach volleyball player, formerly in the top 10 in the world for trampolining, Dux of my school, a certified life coach, have hiked the Grand Canyon, Mt. Fuji and Kilimanjaro, skydived, run away and joined the circus for a year, been a part of the Australian Institute of Sport, competed in and travelled to over 20 countries, sponsored a child, volunteered in Africa, studied abroad in China and presented to hundreds of people.

    Risk is nothing but change. And change is essentially an uncertain trade – exchange something you have now for something different, hopefully something you see as better. Work for money. Training for health. Money for things. And the big one for me – exchanging time for opportunities.

    In the next 2 months I will negotiate a contract for my new job, start a speaking business and continue training for my sport at least 8 times a week. In the long term I want to go to the Olympics and run my own speaking and consulting business.

    Why do I need help? I need help with the trade. What do I give up to create space for more opportunities? How do you let go of something you already enjoy and want to be good at. The hardest part is not taking the step into something new – it is letting go of something old.

    Time, not money, is the true currency of the world. There is so much to do, to dream, to work at, to achieve, to experience and to enjoy in life. But nothing comes free – what are you willing to give up for each new thing you squeeze into life?

    It might have been accidental but my misguided guidance counsellor did give me some good words of advice.

    “Well whatever career you choose, make sure you enjoy it. You don’t want to risk regretting your life when it’s almost over.”

    So the real risk is settling. Compromising when you could have more. Staying safe when a little bit of courage and daring would launch you higher than you thought possible. Be brave, be certain in yourself and trade just a little more of your time for something that might be even better.

  92. This article says a lot about taking risks. It tells us that trying something new or challenging ourselves doesn’t complicate things. I also agree to what this article had written that it’s healthy to say ‘yes’ often since how can we have or attain what we would like to achieve if we will not be open to take risks especially in searching for jobs that suits our qualities and skills. I’m just saying that things do not come in an easy way but in order to achieve it, we should also make an effort to meet our goal in life. As of now, I am taking a risk to have this job even though I am not really in this field but I always believe that by loving your job and learning new things form it, it will make your performance more excellent and it will help you to be a more responsible person.

  93. Tim mentioned that, prior to selling BrainQuicken, no companies were able to create a product of similar success. Why is this? Is it because BrainQuicken (the product) was so good or because the marketing/strategy was done so well?

    I am about to launch my Muse, but am wondering if it’s only a matter of (short) time before the competition catches up…

  94. You’ve covered almost everything that people want. You need to help us with male-patterned baldness though. Are there any cutting edge, non surgical breakthroughs on the horizon? Do any of your food intake suggestions promote increase rates of “Prostaglandin” the protein identified in male patterned baldness?

  95. Hi Ben and Reid,

    I am a social change advocate, professional social worker and a mom – single parent of a 7 year old.

    I have lived my passion for about 20 years now – bring awareness to the issues of workplace abrasive and bullying behaviors as an employment social worker, social advocate, social researcher, health and safety trainer, and workplace behavioral coach.

    I have had numerous successes during my many years of working on this social workplace issue; but always while working within other companies rules and values systems; where at times workplace abrasive and abusive behaviors have occurred but not been managed fairly.

    In my social worker role; I have helped to support individuals targeted by these behaviors,

    as a social researcher – I have contributed articles and reports on the financial cost of these behaviors to organizations, the emotional health risks to work teams, and the impact on organizational productivity and goal achievements.

    In my role as a social policy advocate – I have help obtain the public support to have legislation passed and implemented – Bill 168 in H&S legislation in Ontario.

    I have extensive knowledge, experience and education in group dynamics and crisis management, and counselling individual who are engaging in workplace abusive or abrasive behaviors.

    I have been trying to start up my own consulting firm; however I have not been drawing in the clients I need to drive my business.

    I know this is possible because others I have shared ideas with – have taken those ideas and used their business and marketing abilities to successfully attract the clients I try to target.

    Fact – I am just not delivering my message in a digestible manner to my target audience.

    I think my biggest risk is – fear of being successful because it will change my current life situation – which I feel safe in with my child.

    As a single parent – I know once I start my career track it will provide generous income for my family to provide my son opportunities to be exposed to things I can not afford right now.

    On the flip side; it will also mean moving out of the comfort of having that “stable” but low income from my part-time job.

    I have run a business before; so I am fully aware of the risks as well as the reality of people not paying their contracts on time and running out of money to pay life basic needs – to the point I went in debt against my home.

    I understand fear is what might be immobilizing me –

    I will not give up working through this fear – as this is something I am passionate about.

    My life goal is to help leave our “workplace world” tools and management skills to create respectful solutions to develop respectful workplaces for our children.

    So the next generation can have healthy workplaces to live in.

    I know this is beyond your deadline; but to never take a chance mean you will never be a success.

    Respectfully,

    Tamara Parris

  96. Love this article, it rings so true for me. I know I am way too late but I would like to comment anyway. Well, I studied business at university in Canada and afterwards got a job at private bank. Immediately I knew that wasn’t for me so I quite after about 1 year.

    My two best friends and I decided to go have an international travel experience. So we went to Korea to teach English for one year, we all ended up staying for 7 years. Started off at small languages schools then progressed into university lecturer positions with 5 months paid vacation. These vacation periods allowed me to travel the world over. Then took a year off and traveled to Chile, Argentina, and Brazil.

    From here my friends and I decide to go our separate ways. One stayed in Korea, one moved to Shanghai, and I decide to move to Japan(been here now for 7 years too and just recently got married to a beautiful Japanese girl). I ended up in another university English lecturer position with 5 months paid vacation.

    This time instead of just jet setting around the world I decided I wanted to take some different kinds of risks. I started my own t-shirt company and started doing events which eventually progressed into my creative platform called Illectricsheep.com (2007). This lead me into meeting creative people and sparked my interest in film(complete about 4 or 5 short films). Also I began to volunteer for other events such as TEDxToyko 2011(biggest event outside the original event in California). That lead me into starting my own TEDx event. I became the co-founder and organizer of TEDxOsaka 2011 and 2012, which also inspired other TEDx events in the region). This has lead to a massive group of contacts and connections across many different fields.

    However, I still want to take things to the next level. I plan on walking away from it all. My wife and I plan to move to England where I plan reinvent myself again by pursuing an MA in Filmmaking/Production degree. Finally, plan to move back to Canada after being overseas for 15 years to have a family. When I move back to Canada I plan to volunteer for a bit to get to know the film scene and then set a studio to produce/direct independent films to tell stories based on some of my international experiences, etc. Also would like to give film summer camps to local and international students. In addition would like to help put after school film clubs in schools throughout Canada. That’s about it. It is the first time I have really told my story. Hope it has some value for someone…peace out, gotta back to watching my film, “Ichi the Killer”

  97. That was a really thought provoking article, made me consider what was the overriding deciding factor behind my career choice.

  98. I’m a self-employed financial advisor. I joined this career about 2 years ago, and I’m still struggling to raise my income to meet my expenses.

    About a month ago, I picked up Tim Ferriss’ book The 4 Hour Work Week. I’ve been reading it off and on during my free days. One idea in there intrigued me – that of hiring a virtual assistant. Without knowing how to do it, I told myself to go and do it – get the experience of hiring an assistant, even though I’m not sure what work I’ll assign the person or whether I can afford to for the long-term.

    I’m in the process of interviewing candidates now, but I’ve already learnt so much from the process. My family thinks I’m nuts for wanting to hire someone when I haven’t even earned enough, but I’m of the opinion that having help will give me invaluable experience that will definitely be useful in future.