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.


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 900 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.

Leave a Reply

Comment Rules: Remember what Fonzie was like? Cool. That’s how we’re gonna be — cool. Critical is fine, but if you’re rude, we’ll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)

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

  1. Thanks Ben and Reid for offering this great opportunity.

    I am reading “The Start Up of You” while in the midst of a mid-career level pivot. My background is in journalism, politics and public relations.

    The logical pivots include: external affairs, health care communications, content development & strategy, and brand development.

    Moving in the direction of one or more of these pivots will certainly put food on the table for me and in the kitty bowl for my orange tabby, Oscar. But it would be playing it safe and I’ve done that for far too long.

    I would like to cultivate e-marketing initiatives in developing countries. My past volunteer work has included helping to bridge the digital divide in Ghana and marketing a stove in Honduras that improves lung capacity while reducing the carbon footprint.

    Do I work for myself or do I reach out to existing companies who do this? How do I even find out who they are? Is this a side venture I work on while employed at one of the more traditional pivots or do I go whole hog?

    The risk seems so overwhelming, especially given the need to eat and feed Oscar, that winning the contest would provide tactical, strategic and motivational support. Any help you could give would be appreciated.

    Kind regards,


  2. At the moment I work in the Netherlands for the European division of a US company. I have a permanent contract, a good salary and a job that I made my own in the last two years. … So you could say that I’m in a very comfortable place right now. But therein lies the problem. I reached a point in my job, where the new things I can learn are only incremental improvements. Plus I have a plan B (to use a term from your book) that I want to develop. Therefore I am working very hard at the moment to:

    1) move to Berlin, Germany (the city offers lots of opportunities to develop my skills for my plan B) and

    2) switch into another industry (opportunity to learn new skills for my plan A)

    This move back to my native country brings some risks with it (giving up a permanent position) and some financial downsides (e.g. jobs in Berlin are not as well paid as in the Netherlands). But the upside potential is significantly larger, as the city itself offers multiple opportunities to pivot into a new direction if necessary.

    At the moment things look very well and I could be moving to Berlin in as little as a month and switch from the retail industry into the renewable energies sector. (I work in a Finance position that is very similar accross industries.)

  3. Hi. Thank you for this post.

    I am a biologist who lives in Central America. Biology is one of the careers that has more unemployed professionals not only in Latin America but in many countries around the world as well.

    I am currently working as a professor in an university. However, I am not a stable employee there and I’m only paid certain months. I also work as a freelance Science editor for a company which publishes children’s textbooks.

    Approaching the 40s, it’s difficult to deal with this kind of financial uncertainty; that’s why I decided to make a move. In the next 30-60 days I will work with an online marketing coach in order to create an online business. I will dedicate several hours per week to finish a product in 2 months. On the other hand, I would also like to stop working at my current university and find a stable position in another university, and for that I will start searching for an open position.

    These moves won’t be very risky, because I won’t neglect my current jobs. I don’t need to invest much, just time. Nonetheless, I am a bit afraid that the new online business doesn’t take off as I expect, because of my lack of background in marketing. I definitely need a good guidance.

    Thank you,


  4. Thanks for another excellent post, guys! I’ve read the book twice now and am always inspired to dive back in.

    I recently finished business school in England and am embarking on my first start-up. We’re building an online university admissions marketplace that will pair applicants from India and China with advisors at US and UK schools. Tons of fun and some solid traction.

    To celebrate the end of my time at Cambridge I embarked on an Alpine adventure. I just returned from Mont Blanc where I free-solo-climbed the Italian face (no harness/ropes + no teammate on a challenging route). It was a great experience and reminded me why I love the mountains.

    In the next few years I aim to break into the world of sponsored high-altitude mountaineering. To do so it’s crucial that I build the right track record and network and both these take time. I am all-in on the start-up but am aiming to carve out the necessary time blocks for a couple major ascents each year to adequately prepare myself. Luckily, the team is Seattle-based so the Cascades are just a short drive away but there will be farther flung outings.

    There are several risks to balancing start-up life with mountaineering. My team is seeking angel and VC funding and they are unlikely to be thrilled that the CEO is aiming to take a month of vacation each year to pursue an unrelated interest. My team has been super encouraging of my passion for the mountains. Invariably, teams hit roadblocks along the way and I’m concerned that their opinion will sour in those times of stress.

    So far I’ve dealt with these risks by investing a lot of time managing expectations. I reiterate that I do much of my best thinking in the mountains and that I’ll come back will the batteries recharged. I have assured prospective investors that I am taking controlled risks and that I can and will buckle down when necessary, even if it means cancelling a climbing expedition.

    I’d really enjoy hearing any of your thoughts on work/life balance + long-term career planning.



  5. I want to find a new job. I’m a 21 year old college dropout. I wonder where I can find a good paying job

  6. Hi Ben & Reid,

    My name is Chase Thompson. I’m a mortgage banker in San Antonio, Texas. I got married a few years ago, just had a baby 7 months ago, and I hate my job.

    It pays very well, and I’m amazingly fortunate, but I’m afraid to take risks because I have the only income in my household.

    My wife is very supportive, and wants me to find another job/career/opportunity, but I’m scared. I’m scared it won’t work. I’m scared there will be a hiccup between opportunities, if one comes, and I won’t be able to feed my family.

    It’s crazy to think about being this scared, my opportunities should be endless, but with my wife and daughter at home relying on me, its tough.

    I want to try and get a job at Rackspace. They’re headquartered here, but I’m not a software engineer. My real specialty is media creation, specifically video. And, I think they’re missing a huge opportunity with their marketshare for content creation. I love watching Scoble as much as the next guy, but I want to push them farther.

    Reading this post, then reading more about you guys, and your stories, I’m going to take my chances! I’m going give it just a few days to see if you pick me, but if not I’m still going to try.

    Thank you for the courage and motivation. Here’s to taking intelligent career risks.



  7. I’m currently living out the risk taking as a result of my career change. I am a former Walt Disney Imagineering executive. The rise to that level I learned quickly to take on “extra credit assignments” I did all the dirty work. This was plan to gain experience across the company in Ride Engineering, Audio Animatronics, Project Management, and Creative Development. I even conceived and hosted a global sourcing summit with other divisions of the company when I came back from a 18 month assignment in Hong Kong, so think I have instinctively applied these tactic throughout my career.

    Two years ago, I chose to leave the salary, stock options, and bonuses of the world I had build for a more entrepreneurial adventure chasing resort development in Libya. Revolutions started in Libya seven days before we were to sign a $30M contract. I had risked a very nice corporate job for pursuits and and equity share in a 3rd world country.

    I’ve pivoted to opening my own company that specializing in theme park and themed entertainment development and project management. The first year has been spent doing odd consulting jobs but the real goal is develop and execute a major themed entertainment project. As recently as today there may be a possibility to acquire a moth balled theme park and resurrect it.

    In the next 30-60 days I would love to get meet potential investors/partners, put together an assessment of the opportunity. With some seed money (less $1M), I hope to begin that feasibility phase.

    Our strengths are in developing and executing the plan; however, our weakness is finding investors.

    In short our plan “A” continues to be develop our connections with Real Estate Developers and Owners (strengthening our weak relationships) which we hope will lead to leading a major project through the pipeline. Plan “B” is to merge or partner will design firms allowing the joint venture to share are 2/3 or the pie. Plan Z is to default to straight consulting and/or moving back into the sector by rejoining a corporate owner.

    Personally the risks are truly lifestyle risks. At the moment, all the capital is personal and it likely will run out within the next 6-8 months absent another funding source or increased consulting opportunities. That said, I’m not leveraging my home or putting the kids college fund at risk

  8. I left my 6 figure job one year ago to grow my current company. (Retail stores).

    Company is growing but not fast enough.

    1. I currently have an APP in development.

    2. I am also pitching a TV show I wrote to Networks.

    3. Just starting an Innovative Vending company.

    4. Multiple Product ideas that need to be tested or put into production.

    A lot to do with very little experience with highly productive people. I would love to see how you guys do it.

    Surrounded by the well fed and risk averse.

    D. Ha

  9. I completed “The Start-up of You” a last month. It completely changed the course of my life. The chapter on Risk was a standout. I am a mother of two twenty something’s and have spent most of parenthood fretting over the worst case scenario’s playing out in my mind. After reading the ‘risk’ chapter, it made perfect sense. I know first hand the dynamic of thinking the worst and the worst never playing out. I originally picked up the book to read – to have the ‘information’ tucked away in my brain to debrief with my two adult children. I quickly realized this book was for me. I was a part of a start-up 20 years ago.

    2011 included moving away from my job at that 20 year old (start-up), searching out a new direction and losing 97 lbs. So much in my life has changed. But at the core of who I am, is a creative pioneer spirit born to be a part of new things. I just never dreamed the new thing would be ME. So that is where I am headed, a new start-up where I and my talents, are basically the product. You can not believe how risky that is for a person. It is so much easier to hide behind a product and 97 lbs.

    The Start-up of You is my bible for this new venture. I am challenged to embrace once again the thrill of risk, and shed the fragility that our brains are hardwired to signal. The world economy seems to be screaming to hold onto anything stable, but that will only induce survival. The thrivers will most likely come to the risk-takers.


  11. Well let’s start, I live in Greece. 😀 If that’s not risky enough, I am 29 and I am a freelance musician, which is in the risky jobs that you described already and a lot more riskier in Greece!! On top of that I am on the process of creating my own company with a big idea that I have for a long time now. Working on two “risky” jobs (love them both!) in an unsecured environment is one of the best growth experiences I have already! I totally believe in the long run benefits!

    In the next months I am going to find the right partners for working together and creating the business idea and an entertainment idea into reality!


  12. I’m currently working as a developer, but trying to help my small company become a better place to work and a better company overall. I’m trying to learn as much about improving workplaces for the dual benefits of happier, more engaged employees enjoying freedom as well as companies that attract and retain clients and empower their employees to unleash their human potential.

    In my current position, I often feel like I’m taking a big risk in making suggestions and pushing hard to turn them into reality, because I could be stepping on my bosses toes and possibly even coming off as condescending to my co-workers. And I am waiting to take the plunge and start my own business consulting company, partially because I want to build my experience, learn more, and gain a reputation for successfully improving a workplace, but also because it’s scary to think about finally going out completely on my own and having to find the next client, sell them on the value I will provide to them and then fully manage and produce.

    I’ve never been more excited about the future of my career, though, so I’m working hard to progress down this path every day!

  13. Tim, Ben & Reid,

    Some constructive criticism:

    Overall, you’ve produced an excellent article on teaching people how to manage their pre-wired risk-of-loss bias. It’s got the makings of a classic highly-rated advice article: counter-intuitive, yet highly insightful.

    My criticism, however, is that I think you should cite, or at least mention, Nassim Taleb, whose work you’ve probably read and thought a lot about. Nassim’s new book, Antifragile: Things That Gain from Disorder, is the culmination of his recently refined theories of risk and return. It is especially focused on the counter intuitive insight about how some things actually benefit from shocks (i.e. some things are anti-fragile–they benefit from mishandling). One’s career, of course, could be anti-fragile (like political Italy).

    Citing Nassim could not only enhance your credibility (not that you really need it), but (more importantly) it could also help “spread the word” of another great modern thinker (to those readers who may not otherwise come across his works, and who “want to learn more”).

    All I’m saying is that a little hat tip to Nassim in the article wouldn’t hurt.

    Thanks for taking the feedback. And thanks for the article as-is.


  14. Hello.

    I’m always up for a challenge and love a bit of competition. To be honest, not sure if I would be happier to win this challenge or to get your professional help and expertise in making the right risk.

    Risk 1: Im in that long term low risk or is it high risk short term.. I’m in the healthcare industry. I work at a leading academic healthcare institution on the east coast. I help physicians in 25 different divisions to increase their practices and showcase their sub specialties in 18 counties in a Tri state area. I work for less than 6 figures, and personally upfront about 20-30% of my take home paycheck for work traveling expenses. They reimburse me only if I follow their regulated system to get my money back. I cannot do the work without up fronting these costs, which include insuring my own vehicle that has an increase cost for work travel. I live pay check to pay check and pick which bills to pay that month. I own my house and rent out the upstairs for about 35% of my mortgage.

    As someone recently said to me about my healthcare position, “people get paid ALOT of money for doing all the work you do and all the jobs you hold.” How do I ask for the raise and to stop upfronting my own money without a ROI, but only to “keep my job”?

    RISK 2: I’m going for an interview for a similar position as above. How do I ask for the job I want and negotiate the salary for it?

    RISK 3: I like what I do for work in healthcare. It comes natural to me, as it’s not a clinical position, it’s more networking and bringing key people together. I have always had this dream of being a (sports) clothing or shoe designer for avvery long time. I’ve taken a few sewing classes but am not a seamstress like my mother. I barely can sketch, and have no connections in the biz. People always told me that retail is a very risk business. I have a few ideas but have no idea how to get them started…other than I know what it should look like, and I’ll need high tech fabrics. How do I take the risk of leaping into the unknown territory without losing it all?

  15. Dear Ben and Reid,

    I am 21 interning at a large company in product development for consumer packaged food goods.

    -I am working here till the end of August and till then I’d like to pitch specific changes to the way they currently operate at the “innovation” level.

    -Essentially the change I’m advocating is the use of more metrics/quants –a lot of their new products come on the market by “gut feelings” and not fully supported by market analysis (there is some).

    -I’ve already asked for sales numbers and more data and drawn up simple charts for my team to make decisions. I’d like this to become something more permanent in their process.

    Thank-you for your insightful post!


  16. Hi guys, Chris here.

    The cole’s notes version: 29 years old, been with the same large company since I was 17 sweeping plant floors and now I am in middle management after a few good breaks and a ton of hard work. I even keep a picture of myself as a kid next to a company vehicle (dad used to work there) on my desk.

    After a great decade of tremendous growth, learning and experience I now find myself wondering is this all it’s going to be? After breaking through the Gladwell “10,000 Hour” plateau in my current role the challenges of the day to day, year to year are more routine and boring than engaging and challenging.Don’t get me wrong, i’m treated well, good perks and well respected but it seems to not be enough. My 17 year old self who grew up in the “rough” part of town would kick my ass for even thinking it isnt enough.

    So in the nex 30-60 days I have two choices, keep doing what i did the last 30-60 days (nothing and little growth) or get growing and start living. So im going to look for other opportunites outside my company. I know that experience in another company or a different field will restart my growth and I’ll be better for it.

    How do I rate the risk? well, it’s a little scary right now (my brain is still wired like the caveman) but hey what do I have to lose? I got this far from starting sweeping floors so theres no reason it can’t happen again!

    P.S. I’ve seen the number of posts in here so far and it’s a long list… so if you didnt get to mine or you choose someone else I still have you to thank for the first step for me which was to actually write down how I feel and to start making a plan to change. – Chris

  17. So much time and so little to do. Wait a minute. Strike that. Reverse it.

    There is no life I know to compare with pure imagination. Living there, you’ll be free if you truly wish to be.

    -Willy Wonka

    My name is Molly, and I am a 23-year-old word artist hoping to make a foot print on this great big ball of dirt. I’m a bit bizarre and definitely dance to a beat most people unfortunately don’t seem to hear.

    Recently, I proclaimed ‘I AM A WRITER’ quite obnoxiously for Jeff Goin’s You Are a Writer contest imitating the famous Gerard Butler ‘THIS IS SPARTA’ scene from 300. Check it out here. I won runner up # 2.

    Right now I am working as a web content writer for a Halloween costumes website, which I have only been at for a few months. The company is awesome, but the only issue is that it’s the 40 hour-a-week grind we are all quite familiar with. I’m a free bird at heart, so the hours spent in one building for such a significant chunk of my week is squashing the reality I wish to dwell in. This reality sunk in when a co worker tattled on me recently for not spending as much time at my desk at as the rest of them. Sigh. Another cold hard slap in the face reminding me that I check my freedom at the door when I clock in. I took a risk with this job because it pays a hair above minimum wage hourly, and I’m learning lots in a small company which is growing rapidly.

    However, underneath it all, the biggest fear I have is wasting my time doing the wrong things. My time. Time, and what I do with it are so important. My feet are itchy with all the running wild I need to be doing. Writing is something I love but in a little a box all day? No way. When I accepted this job, my dad asked if I think a wild horse can be tamed. Nope. No taming this brute of a female.

    The question isn’t who will let me. It’s– who will stop me?

    -Ayn Rand

    Because of the time engulfing qualities and low pay of my job, it’s been hard for me to focus on moving forward with what I truly desire. I know it’s possible, but I’m in between learning in a fun company and an overwhelming urge to see the world, but not quite enough paper in the bank to give me some elbow room to research and spread my wings and fully focus whole heartedly on my goal. In my ‘free’ time, I also write for which I LOVE. I’m infatuated with the brain, and it’s crazy amazing role in our lives and the world we live in.

    Anyway, in order to dive into what I am passionate about, I’ve asked myself how the FUCK can I travel, write and have money to fill the belly and pay off all this wonderful college debt? Well, I have started looking into delivering vehicles and truck driving for a living. I’d love to see the look on my mother’s face when I tell her I quit the job that was supposed to be the seed to my blooming career to truck drive across the US. Instead, I’d be spittin’ seeds out of my face tootin’ my own horn. Oh boy, it sounds glorious. I am hoping to find ways to deliver RV’s or vans cross country. Semi’s are a little daunting. However, I’m open to what I can find to start gaining experience. Eventually, I’d like to create an online business and pick up freelance writing projects along the way.

    I’ve looked into Craig Chilton’s program at which involves vehicle relocation and resources to find jobs, so I can forage my large appetite to make the entire country my backyard. Eventually, with frequent flyer miles built, I hope to make the entire globe my backyard.

    I am also a member of Cody McKibben’s Digital Nomad Academy where I have been exposed to terrific connections. At this point, I am teetering rather precariously between information overload and falling head first into a life erupting with no limits. Instead of hiding, I am choosing to face the storm (aka the risk) head on. Not apprehending the possible destruction but embracing the beauty in a little chaos. I’m sooo close. I just need to narrow the focus. And I’m also feeling a little guilty for wanting to leave a cool job so early. I know what I want. I see where I’m headed. I just need One. More. Push.

  18. Hey Ben and Reid,

    I’m a big fan of your work. I have read through the Start-up of you a few times, and I have been a fan of Ben’s blog since I stumbled upon it through a link on Cal Newport’s blog.

    I’m a PhD student of Entrepreneurship at Indiana University, and similar to Reid, I would like to do work that impacts the universe. Also similar to Reid, I realize that being an academic will not get me there.

    That being said, I recently started working with a technology startup that I believe could have a transformational impact on African economies. I love their product and I would love to leave my PhD program and begin working with them full-time.

    The risk is that while I believe that co-founders are talented, I honestly don’t know if they are talented enough to succeed across Africa. It’s not that i doubt their talent, but I just met them and we have not had enough interaction for me to judge. They also have not offered me a full-time position, but I would have to convince them to.

    To add more downside to the risk, I have been in my PhD program for 3 years and would be due to finish in 2 (I try not to subscribe to sunk cost fallacy). I enjoy academia to a certain extent, but it’s not fulfilling in that my work would never have an impact on people I feel an obligation to. I could certainly somehow squeeze a life of impact into the academic position, but I would always be swimming against the current.

    I believe the risk of being an academic are higher than being an entrepreneur (tenure will disappear in my lifetime), but is it riskier to be an entrepreneur on the African continent where the jolts are seemingly higher?

    What is one to do?

  19. Hi guys,

    I enjoyed this article and I feel this is a great opportunity for whoever can persuade you to “take them under your wing.” This article got me thinking about my own situation and how risk played a factor in my career to this point.

    I grew up in St. Louis, MO and went to college there, got a job, got married, all the things you are “supposed” to do to start a life. Some of my friends moved away and some stayed because they were comfortable doing what they felt was right.

    I worked full time while in college as a videographer for almost 5 years taping depositions for court cases, boring work, but it was interesting. It paid my way through school and taught me some very valuable lessons. One that I didnt want to be a lawyer!!! Two, it taught me responsibility. Not only was I paying for my own college, but I was working on some of the largest class action lawsuits in the United States at 22 years old. My videos were of the utmost importance in some of these cases. The jury would ultimately rely on video of witnesses or testimony of doctors that couldnt be in a court room at the time of the trial. So if I missed something, it was a big deal. You can’t ask a doctor to re-explain “false symptoms” in a smug manor, because the person was lying about an injury. That was my first real world experience in a small business and I loved every minute of it. I did everything from shooting, editing videos, scheduling, sales and day to day operations while my boss was skydiving or traveling Europe…. He has over 5,000 jumps, so I believe that qualifies him as a professional…

    My next couple of jobs were not as interesting in my post college life. I worked at two of the largest home health and staffing agencies in the United States. I started off as a recruiter. Recruiting nurses for pediatric home care cases. Then moved into more of an operational/training role for our office. Then moved on to strictly staffing nurses on contracts and temporary assignments in hospitals. Nursing is an invaluable profession, but they are some of the most demanding people I have ever run into. I will call that the character building chapter of my life.

    As I searched for more meaningful work and really was taking a hard look at what I wanted to do, my friends were moving away and working for successful companies. I had just gotten married and didn’t really want the risk of picking up and starting over somewhere new. Then that changed.

    My cousin bought a durable medical equipment company in SW Florida. It was a family owned and operated business and the owners were on cruise control and not thinking about growing the company. My cousin purchased the company in 2010. He asked me to come down and help run the company while he traveled back n forth weekly from Illlinois.I figured what the heck, it was a great opportunity and would give me the real hands on experience I would need to take my career to the next level.My wife and I sold our house and headed south!

    From the start I was enthusiastic andI jumped right in. I started doing deliveries with the drivers, learning the fulfillment side of the business. I started obtaining new contracts with managed care companies, increasing our product mix from 5,000 products to 15, 000 products. Hired and trained new staff. Volunteering in the community, I sit on 5 boards and volunteer with the local American Legion, and selling our services. It was great, we grew over 30% in our first year.

    Now things are changing. Medicare is 65% of our business. They are paying out at a minimum of 120 days and it is a constant battle to justify services we are providing to the customers. The daily operations have moved from trying to grow to trying to survive.

    I was excited about this opportunity and knew the risks involved, of moving, working with family, and going into a difficult industry. Now I am burned out, cant stand working with family, and feel stuck because my networks here are all healthcare related and I dont have the desire to tranisition into another position in this industry. I have been applying for jobs back in St. Louis and other places, but most companies I have talked with want someone local and they are mostly positions I know I will never really like.

    So what I am looking for is a career change in the next 45 days. Full on career changing opportunity. I want to work in a completely new industry that is fast paced, with room to grow based on success, either personally or in team environment. I am a person that loves to be around people and take challenges head on. I am open to moving anywhere in the country, will travel, whatever it takes to start a new venture.

    The risk involved in a new opportunity is not having experience in a new industry and moving to another unknown area. I have been involved in healthcare over the last six years and it has taught me everything I know now about business and operations. Those skills can be transfered to another industry, but there will be a learning curve. I feel those are valid fears, but they are not anything I cannot overcome.

    Thank you for taking the time to read a little about me and considering me for your project. Good luck to whoever wins and hopefully he or she appreciates this opportunity.

    Jim Smith

  20. My name is Jake Johnson. I will be a junior at Tulane University in New Orleans in the Fall. I believe time is the most precious commodity, so I will be thorough and succinct. Although I’m anxious to set sail into the wild world of my own career, I am grateful that I still have more time to narrow in on what I’d like to do. Sometimes I feel limited by my wide range of interests. Talk about paradox.

    In the next 30-60 days I am considering cutting myself off from my provided college fund so I can learn to be more independent and manage of all my finances. I know it may seem irrational, but I believe in taking the hard road while I am young as this will increase my later happiness. I am considering the hardships that will come with struggle, but more importantly the room for growth that comes from a feat like this. I have been lucky enough to grow up in one of the most beautiful coastal towns in Southern California. After living in New Orleans for two years now, I understand the adversity that some people face and I’d like to come out a stronger individual.

  21. Ever since leaving my first job to move to Shanghai without a job, an apartment, or a plan, I’ve switched between travel and going back to working in advertising to save up for the next trip. After finally making it to the top of my career I finally decided that this time around I am really leaving advertising, an industry I never really loved but was easy for me to find work in.

    I’ve decided to go for my master’s degree in the UK studying cross cultural communications and working on research under Sugata Mitra on using technology in education. While in school it’s my plan to implement scalable community building ideas for integrating international students with the local community. As part of community building across different groups I am working on facilitating cross cultural communication through the natural act of eating dinner.

    I read Tim’s book back in 2008 and was adverse to actually taking the risk of leaving a steady income and quick growth in my career path, but the lure of travel and bring people together has always called out to me, now I’m ready to REALLY walk away from what I always considered “a sure thing”.

  22. My name is Frankie and I’m 23 years old. A year ago I graduated with a BS in Applied Economics and was on track for a finance/investment banking/consulting career path. I was also 1 of 3 people (out of 350) accepted to an Ivy League MBA program straight out of undergrad.

    I turned this all down because my heart wasn’t into it.

    I took a year off to move home, travel and to think about what I really wanted to do. I’m fortunate enough to have enough savings where I was able to do this and also make student loan payments. Many to this day think I’m foolish because I gave up a years worth of salary; however, I’ve learned that I’m happier right now having less “crap.” I also realize I will never get to spend this much time with my family again and am more interested in learning right now than earning a great starting salary at my first job. I also have taken up an interest in online marketing and currently have an unpaid SEO internship for a popular website to learn more skills.

    In the next 30-60 days I want to relocate from Miami to Los Angeles and find marketing work at a B2C tech startup with less than 100 employees. I think technology companies (and entrepreneurship in general) are platforms for having the biggest impact (as opposed to finance companies creating more problems) and will offer the greatest opportunity to learn and put me in a position to start a company later on down the road.

    The biggest risk is that I don’t find a job. But, I realize I am a fast learner and have the clarity of mind and energy to put everything I have into it. Also, I do have extended family members that I could live with in case times do get tough (or I could move home again).

    I’m OK having less money in savings and taking a low-paying but high-learning job. I’ve been living this way for the past year. I know that soft assets pay off more in the long run and I’d rather be focused on the long term rather than the next couple months. I’m also happier doing something that I enjoy while having enough money for necessities. A lot of my friends dread Monday morning and gave up their dream job for $5k more in salary at a job they convinced themselves they wanted. I refuse to be that way.

    I’m ready to take the leap this summer.

  23. This post is just what the doctor ordered as far as I’m concerned. I’m a senior developer working for a ‘stable’ company. As I have grown tired of programming and writing endless lines of code, I began looking for something more meaningfull to work and found it – user experience – mostly information architecture. I have always been good at looking at the big picture and reading between the lines.

    My husband (a UX designer) has offered me an opportunity to work with him at his company and gain much needed experience in UX. This is a risk I would gladly take as it offers imense learning opportunity but having two preschoolers is something that is stopping me. A steady paycheck is what pays the bills and puts food on the table for my kids.

    However, I’m stuck in a rut. So, no more choosing unhappiness over uncertainty for me.

    I’ve made my choice even before I read this post and I will take the risk – it’s really not that big of a risk anyway.

  24. I’m considering leaving work to start a couple of project that will turn into businesses. ( & I’ve been working on them for a while and it’s soon time to take the plunge.

    I think about the risk in terms of impact on those I’m responsible for – family. I need to focus more on the potential hugely beneficial outcomes, but it’s a daily battle to not think about what could go wrong….

    …but I guess I’ll regret not doing it, whatever the outcome Geronimo!

  25. Hi guys, here’s a bit about myself:

    I’m a Dutch national from a tiny village on the border next to Germany. After taking a huge risk, I ended up living in China of all places. Currently I’m residing in a coastal city near Shanghai, China, where I am involved in setting up a new type of language school for foreigners wanting to come to China to learn the language, create “guanxi” (network) and get confronted with Chinese business people and their way of doing business.

    I just turned 24 and I’ve been in China for 4years now working all kinds of odd jobs, from modeling & acting to lobbying for Chinese companies with local government officials and waiting tables at local restaurants in China and Korea. I became an “entrepreneur” when I was 11, building websites for small companies. Then I started selling parts for mopeds and selling old mopeds from Eastern Germany to Holland, I imported and sold small art pieces from a tiny village in Thailand during my first year in college and I’m now waiting for my first big break-through!

    Also, I am about to graduate from university (post-grad) and already delved into an HR business connecting Chinese businesses with foreigners in a unique way. The goal is to create a networking model that eliminates the “guanxi” aspect through a new and innovative way, amongst others. Several Chinese businesses have showed their genuine interest and I am positive that this will be a game changer within this specific market in China.

    The risks are quite high, since I recently lost most of my money in an investment that still has not paid off and will probably not pay off for quite a bit longer. Also, I lost half of my belongings after my bags got stolen 2months ago, causing the number on my bank account to drop below zero.

    I am running a risk that the government will shut down my project due to new regulations. Although being perfectly legal, in China you’re simply not the final decision maker..

    It’s a turning point for me: I’ve been studying and working my ass off, learning new languages, travelling to the most distant places and trying to find my place in a completely different environment. It’s been fun, but it’s time to take action now. I’ve gotten myself in the most strange positions one can imagine, from dining tables in a small village in South-Korea, to sucking up to Chinese government officials, and I’ve loved every bit of it. I’ve just never had the chance to meet an internet entrepreneur or even someone close to that. To be honest, the closest I got to the ‘tech world’ is living next to the giant AliBaba & TaoBao buildings here in China.

    I’m driven, successful (as in reaching my goals, not money wise) and have never turned down an offer to learn something new and exciting. As was written in this post: sometimes just say Yes. I’ve done that, and yes, that’s gotten me into some very uncomfortable situations, but the perk is that I’m simply not shocked by anything anymore and feel comfortable in most environments.

    My concrete summer goals: set up the HR business as discussed earlier, become friends with certain influential government officials here, and make enough money to travel from the South of China to Amsterdam by train, to be able to finally see my relatives again!!

  26. In 2009 I was a mediocre sales agent and I got fired. I then went to a Empretec work shop that change my perspective. I got a new sales job where I was the number one (in a team of six) in 2010 and 2011 and launched with an acquaintance a on-line shop. The on-line shop did not work out, but I learned a ton of stuff, including about the importance of team work and the importance of choosing the right partners :). I am at the point where I will launch in two weeks a new venture a financial education site for Romania, my american model is: Is not something very risky for me, but I can still use the mentoring :).

  27. I thoroughly enjoyed this post and it has motivated me to continue to persevere in pursuing my dreams. I recently read a quote from Thomas Edison that stated, “Nearly everyman who develops an idea works at it up to the point where it looks impossible and then gets discouraged. That’s not the place to become discouraged.” That’s the point where I am.

    I quit my job Oct 2011 to take a 2-year career break and pursue my dream of going on a trip around the world. I previously served as a Peace Corps Volunteer when I graduated from undergrad, but wanted to redo the experience now that I had more professional experience and a Master’s Degree. So I started my trip around the world by serving as a Peace Corps Response Volunteer in South Africa. Also, I decided to couple my trip around the world with my desire to help artisans in developing countries, by starting an online art gallery exhibiting unique, handcrafted, fine and traditional arts from around the world. I want to empower artisans in developing countries and sustainably improve their quality of life, while providing an education to my consumers on the artisan’s country and culture.

    So to answer your question, the big (or bigger) risk I will take in the next 30-60 days is further investing in my business. I realize now that I was overly optimistic in my ability to continue to pay on my mortgage note worth of student loans, travel the world, volunteer, and start a company. With set backs I have experienced in things like getting the website launched, I was considering forgoing starting the business. Your post has inspired me to rethink my model and figure out a way to accomplish my goals more efficiently. Also, I am giving the company only a year and if doesn’t work out then at the end of my travels I go back to working in corporate America. I figure at least I took the risk and learned from the experience and also got to travel around the world! Hopefully, as you mentioned, if I do have to go back to corporate America, this experience will be appreciated!!!

    Thanks Tim, Ben, and Reid for this opportunity!

  28. I went from a construction worker with nothing but a high school education, to the owner of a large successful real estate brokerage, a title company, and a real estate holding company. I did all this by taking educated risks (or mabey uneducated, depending on how you look at it)

    Your message needs to get to our children. They need to take risks and follow thier dreams.

  29. Hey guys,

    No need to reiterate, this post was just awesome! And this is what I needed right now.

    The questions you asked were the one I was pondering over this vacation. Thanks a lot.

    Just to introduce myself, I’m a law student, interning in a law firm right now which made me realize how deadly the so called stability or stereotype life can be.

    – 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)

    I plan to convert my blog on law school into a site with a legal directory and all the tit bits about law school. Also, I’m working on my e-book on how hack life in law school.

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

    I’m not going for a conventional law firm job which everyone in top law school covet for and planning to self employ myself.

    Thanks a lot 🙂

  30. Great post, very well done.

    Here’s an analogy to your deconstruction of risk. I can’t take credit for it as it came from a guest lecturer I had in school, but here it is none the less…

    The steady career worker is like a chicken. He’s given a nice coop to sleep in, people clean up after him, his friends are all around, and he never needs to worry about where his next meal comes from. Life is good until the 365th day in the coop when he’s brought to the butcher.


    The entrepreneur is like a hawk. He never knows where his next meal comes from, is often found in isolation, and is forced to scour the ground in search of new ways of finding food. His life is marked with short term ups and downs, but when trouble comes, he simply rises into the sky to fly away.

    So to your point… I’m a trained “wannapreneur” who has started many initiatives within companies but not something on my own. I’m in the process of breaking out of the brokerage firm I work for to pursue a muse of bringing technology to investors so they can fire their broker and adopt the principles of the wealthy. Maybe it’s just me, but paying Wall Street advisors 1% to underperform doesn’t seem to be working.

    In the next 30 days, I’m going to (and already have begun to) start to find a technology co-founder who can help hack into this idea.

    Problem is this… my firm requires any “outside business activity” to be approved (read: denied) and they just began monitoring our LinkedIn accounts and implemented a policy that we take off all “contact me for…” requests.


    I’m starting this muse – but it’s not without fear of loss. Unfortunately the big brokerage houses in the finance industry are no Google, and instead, force innovation to happen in shadows and fear.

    How do I make this leap?

    PS: I used initials here because even this post is supposed to be run through my compliance department… See email for name.

  31. Hi, my name is John and I’m 18 years old. It was around this time that I told my parents that I would not be returning to school to finish my senior year. I had spent the summer worrying about my future and what I was going to do after graduation. People were asking me serious questions that I simply did not have answers to. To make things worse all of my friends seemed, or pretended, to know exactly what they wanted to do. I was reading “Striking Thoughts – Bruce Lee’s Wisdom for Daily Living” in between finishing “The 4-Hour Workweek” for the second time, when I struck a note of clarity. One of Bruce’s tips for dealing with adversity was that, “You cannot clear muddied water with your hand.”

    I decided to listen to him and take a trip to discover more about myself and what makes me happy. I knew It would present the perfect growing opportunity and I would be able to let all the silt clouding my mind settle into lucidity. I was resolved. I would finish my senior year online and then move to Australia for a year. I used the 80/20 Principle to convince my parents, as well as myself, that I was being responsible by finishing my senior year in record time online instead of partying and skipping class for a whole year.

    I picked up more hours at the credit union where I worked as a teller to save up for my trip and if the 80/20 principle weren’t true enough; I finished my senior year in three and a half months. I bought a one way ticket and left home with one duffle bag and two thousand dollars. Melbourne has been great to me and Australia is full of great people. While I was meeting people I lost all of my money waiting to get paid by a dodgy company in the first two months I was there. I was broke, the company hasn’t paid me to date, and at the time it seemed like I had failed in record time. I applied for work everywhere and became the assistant manager of a video game store, GAME to be specific. When I got my first paycheck I had fourteen dollars left. While I was promoted to store manager within two months and was able to improve the performance of my store by a significant margin, the international chain went into administration just two months later. Two weeks since the store closed and I have only just worked past a major crossroad.

    With only 6 months left in the country, fear set in. I told myself I could get a full time job and save money furiously, I mean I’m supposed to be going to Thailand after this and then even further abroad! However, when I crunched the numbers I realized that I would need to work as a senior geologist in a mine in Western Australia for the remaining six months to be able to leave Australia with the amount of money I wanted. I had fear goggles glued to my face and couldn’t see any positive end in sight, but after rereading “The 4-Hour Workweek” I knew it was time to make a change (You’d think I would’ve learned the first two times I read it!). I would get a casual or even a part time job at the most just to pay the bills while I would tackle my first entrepreneurial venture.

    Worst case scenario, I would run out of money and be forced beg on the streets and steal McDonald’s from people to avoid starvation; I mean, hey, it’s worked for other homeless people here quite often. More likely, I could borrow money from my parents for a ticket home where I could just try again. If I fail again after that, I’ll just be sure to fail a little better. I can deal with that. Risk can be a great thing, by putting yourself in risky situations you force yourself to new heights. Despite the risk, I feel confident the next six months will be a positively defining moment that I will always remember no matter the outcome.

    Looking back on it all, I can’t help but laugh; I have learned and grown more than I ever could’ve by doing what was easy and finishing school traditionally. The biggest lesson: priceless opportunities lack affluence, require ambition, and amplify you in every way possible when it’s over. Finally, here’s my favorite excerpt on adversity from Bruce Lee, “With adversity you are shocked to higher levels, much like a rain storm that is so violent, but yet afterwards all plant grows.”.

  32. As a former college athlete and lifelong competitor, I have a passion for sports. Recently, a friend and I have decided to set out down the entrepreneurial path and see if we can create a business that gives sports fans a level of access and interactivity they are not currently getting. As a basketball player, I believed I never hit a shot I didn’t take. Likewise, in business, I’d rather be a statistic of failure than a statistic of inaction. Even witha partner, as a first-time entrepreneur, I realize I’ll need all the help I can get. I’m willing to listen, willing to learn, and willing to fail my way to success because I know that sports fans are passionate, perhaps even a little bit crazy and I believe a business can built giving them what they want and aren’t currently getting.

  33. Our risk level fluctuates with our lives. In my younger days, I tried sky diving, rode a motorcycle then took up hang gliding. And there I stayed for awhile. I loved the feel of flying and I knew the risks (though I might not have believed they could happen to ME). Four broken bones later, I would have kept flying, but I got married and started making babies. Funny thing happened then – I realized that risks that were okay for me, were NOT okay for my kid’s Mom. Suddenly, I wasn’t just me, I was someone’s Mommy and Mommy could not take the chance of having broken arms (hard to change those diapers).

    Now, here I am, over twenty years later, having spent most of those years as an At-home Mommy, I am beginning to be free to be just me again. Oh sure, there is the husband to consider, but he is ever supportive. So I am beginning with baby-steps risk wise. I am planning a solo trip to Death Valley in a few months. The very idea scares me, but draws me as well.

    But, but, but, but – the biggest fear factor comes from the “What am I going to be when I grow up?” question. I started a Virtual Assisting business almost a year ago. It is beginning, oh so slowly, to take off, but I find myself in a constant battle with my “Mommy-mind”. My M-m thinks I should just forget about this and get a “real” job. We have debt to pay and college expenses and the house needs painting and on and on and on…

    The M-m says that my business isn’t growing fast enough and even if it were it is never going to bring in the kind of money I would like to bring in. The M-m is very cautious and very hard to shut up!

    Just yesterday I thought, “I wish I had someone to help me with this business” and I didn’t really mean just my VA business, so much as I meant the whole idea of multiple income streams, the finding of alternatives to becoming someone’s Administrative Assistant. Caving in and getting a “real” job just seems so much easier than trying to find my way through all the information I can find on the internet and in books. And yet, I know that, for me, the right path is the one that takes me somewhere unusual. I would love to have someone to talk to, more to the point to listen to. To bounce ideas off of. Guidance. I would love to have guidance. I would very much appreciate it if you would consider me to be the one to receive your assistance.

  34. In the next 30-60 days I’m planning to change jobs and move into a senior position for an established retail company. I am currently in a position that is not demanding, but the corporate culture is decent. My skills are in online marketing and I’ve been working in eCommerce for over 8 years now. I also just finished my MBA last month. The goal with my MBA was to make myself more attractive to potential employers and learn more about leading a company. I have had a lot of phone interviews over the past 2 months, but nothing has panned out.

    My wife and I own an online business selling baseball goods that I enjoy working on, but it is just a side project. We are utilizing dropshipping many of our orders, but a large portion are products we manufacture. We have trademarks for the names of our products and a couple of patents. One of the patents is for a great little device for baseball players to measure their bat speed. I have several prototypes, but I need funding and connections to get this product in front of the MLB and big-box retail stores.

    The way I see it is that I have several options. I can go for the new job/career, make good money, but have less time to work on my side business and new product. Or I can stay where I am now which offers me the free time to work on the side business, however, I’m not making much money and feel stuck every day.

    If I don’t move to a new company soon, I plan to use the 4HWW tips on asking my employer to allow me to work remotely and then I’ll have even more time to grow my side business, make enough money to fund engineering for my patented device and either sell the IP or get it into big-box stores across the country.

  35. Thank you for this post – I recently picked up the 4HWW again two days ago after I purchased and read it in 2010, during my first year of business school. Needless to say, I am glad I picked up the book again and saw this post today.

    -About Me:

    I am a 25 year old living in Boston and one year removed from completing my MBA in June 2011 (I received a BA in Economics in 2009 and went right to grad school). I work in business development for a San Jose, CA based start-up that manufactures and sells tree-free paper products. I work remotely and am one of 2 people that the company has on the east coast and both my colleagues have 25+ years of selling experience within this industry, while I am going on 1-year.

    I was introduced to this company through an alumnus of my grad school, who is an advisor to the company – because they were looking to try something different by taking on a younger salesperson for the northeast US.

    This opportunity began as an unpaid internship for 3+ months (June-Aug 2011) as the company was not yet sure if this experiment would be fruitful for them, and they were unable to pay me (being a start-up). Each side took a risk as I passed-over traditional MBA opportunities that would pay me more than double what I make now full-time (started Sept. 2011) – and the company chose a ‘kid’ develop its business here in the northeast.

    – 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)

    In the next 30-60 days (closer to 60) I want to ask for a raise along with a new opportunity within this start-up, which involves filling-in the void that we currently have in marketing. As of now, we have a marketing department of 0 and I created some of the programs we currently have including social media and a partnership with a not-for-profit. Even though I still have less than 1-year of experience within the paper industry and less than that with sustainable products, I have a grasp of the market and have ideas on how we can grow this business in a new creative way (the paper industry is over 100 years old, and ‘new’ usually doesn’t happen).

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

    I am thinking about the risk involved in this move in 2 ways (A and B):

    A: There is a perceived risk for the company, who has already taken a flier on me, because the most ‘inexperienced’ person in the company (with no paper background) will be in a decision-making role within a department that does not exist today. They might rather hire someone with more experience to fill this role, which would be safer for them, but would cost them more in total compensation.

    B: The risk for me is that I may be overstepping my bounds by asking for such a promotion within a year of working for the company. I am effectively asking for more responsibility, decision-rights, and more compensation. This action may be perceived as me being over-confident in my abilities as well as entitled since I have a MBA and a relationship with an advisor. Neither are the case as I have demonstrated my abilities and have brought additional actionable and measurable ideas to the table (that we have used), without asking for more compensation.

    It would be very helpful to receive some mentoring and advice on how to best approach this situation to minimize the company’s perceived risk if they agree to my proposal as well as my risk of being perceived as overstepping my bounds and asking for too much too soon, which I do not believe to be the case.

    Thank you for your consideration.


    Michael P.

  36. – 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 two years out of college with a life science degree currently working as an Assistant Scientist at a Synthetic Biology startup. I have worked 60-80 hour weeks since I started and have been promoted (without compensation) into a more defining role. The company is currently experiencing growing pains and has had a round of layoffs, effectively reducing our staff by half, to align themselves with a new CFOs vision.

    This makes it difficult for me to ask for a raise, and has me scrambling to find work elsewhere. I have a broad laboratory skill set and could easily adapt to many different roles, but am having a hard time marketing myself. In addition, I have considered working on the finance side of biotech, and would enjoy some foresight into getting my foot in the door at an life science equity research firm. If neither of these plans work out, I am considering going back to school for a doctorate. Being in my current state of limbo is not very appealing and would greatly appreciate some advice.

  37. “Every time you’re making a choice, one choice is the safe/comfortable choice and one is the risky/uncomfortable choice. The risky/uncomfortable choice is the one that will teach you the most and make you grow the most, so that’s the one you should choose.” – Derek Sivers

    That sums up how I try to look at life decisions, such as posting my first ever blog comment here. The real risk is NOT acting or just thinking about doing it.

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

    I want to follow through on the risks I’ve already recently made in my career (ending regular employment for a Fortune 50 company and starting a small apparel company and an athletic coaching firm specializing in 1 on 1 evaluations). This was done because it was riskier for me to continue on the track of doing something I didn’t like and did not make me grow as a person. I’ve made the initial jump to getting started, now I want make one or both businesses prosper. I’m in the difficult stage right now financially, and need to continue to push towards success instead of succumbing to negativity bias. I want these businesses to become financially sustainable in the next 30-60 days, but there is an indirect way to making that happen.

    For example, I read about a entrepreneur I wanted to emulate. I tracked down his email address, set up a meeting, and he offered to mentor me. Huge opportunity.

    Focus on passion and creation. I am that person who is pivoting into a new industry and feeling re-energized by the challenges. Capitalizing on the risks you’ve already taken and seizing it as an opportunity is a challenge in itself, albeit an exhilarating one from my point of view.

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

    Just like I’ve attempted to approach all other risks in my life: by trusting myself, my wants and needs, and what is really important to me as a person. Being a successful entrepreneur is a central goal in my life. I’m already out on that bridge, and I’ve looked down a couple times and I have a long way to go until I get to the end, but continuing to learn and welcome challenges and capitalizing on opportunities with a specific goal in mind alleviates the risk.

    Through this post I have realized and become more comfortable with my “risky” decisions even though I’m surrounded by doubters. A good example would be dropping out of law school after 1 year because it would have been far worse and riskier to stay the course and do something I despised.

    For me, the biggest risk is being content.

    I am far from content right now, and having the passion and pride to view your life decisions as opportunities as opposed to road blocks or brick walls is important. Constantly adapt and change for the better while staying true to yourself is the least risky thing you can do.

  38. I enjoyed reading the risk art As a fulltime pastor , I made an acronym of your suggestions: RISN (He has risen) and this is a good way for me to remember your suggestions. I am at retiring age and am contemplating the idea to start writing freelance to ad to my pension. Though a bit stuck; do you have suggestions on topics, websites etc to which I can direct my quiries?

  39. I am a twenty-five year old Chicagoan who has been interloping among risks from music, to travel, to politics for years. However, there is one persistent idea that has left me with an incredible desire to fulfill and has stuck with me for the past two years and I would risk with great effort to see what astonishing results may follow. Thus lies a necessary change to be made.

    Within the next thirty to sixty days I want to establish investor relations in my career to propel my company idea to the next level of operation. I want the opportunity to prove to investors that my idea not only would be a disruptive technology but, with the proper funding and planning, would be cashflow and userflow intensive.

    Being a man of risk, I know there are ways that one can jeopardize or inhibit a start-up idea by pairing up with investors that may run the idea astray or into the ground. Therefore, it is absolutely crucial to resonate with the investors and establish a bond that can enhance the growth of one’s fundamental idea. Therefore, I do see this as a potential risk I’m willing to take.

    Additionally, I know that capital in most cases can return if one is willing to say ‘Yes’ and spend the time to know the host. Simultaneously, while going through the process of establishing contacts, one begins to weed out what/who is fit and not fit for the necessary change at hand.

    Moreover, relocation on a budget can also be a big risk. In some cases, relocating a company or an idea is highly possible and necessary. The risk itself, due to finding a way to re-stabilize oneself in the new geographical and entrepreneurial environment can be worth the tremendous experience and knowledge.

    The risk variables mentioned above are significant components to the equation of a successful change in career and those which I am thinking about. Of course, the right placement and execution of such variables will determine my success.

    In closing, I hope that I may resonate with you Ben. Thanks!

  40. I really enjoyed this post. I thought that graduating during the recession was a bad thing, but in reality, it was good because it allowed me to discover what I was interested in.

    Over a year ago, I was approached by a friend, who was the editor-in-chief of the school newspaper about being their blogger.

    I had a vague idea about blogging and the position wasn’t a paid position, but I knew that I had to take the offer because I would learn something from that experience.

    Along the way, I realized that though I was working for them, I was simultaniously working for myself because it was my blog and after a year, they went in a different direction and at the same time, I incorporated my blog into a website and started my own online media company.

    This post has shown me that it is o.k. to take small calculated risk to get use to volatility.

    I also spent the summer in Chile after I graduated, studying and interning at a marketing company.

    Thanks for the post.

  41. Hey guys,

    Recently read the 4HWW and enjoyed reading this (and the great article photo) as much as I enjoyed reading the book, which is saying something.

    I am a 22 year old British student who has just finished a Master’s degree in International Economics in Sweden.

    On the 10th of July I am leaving for 2 internships that I have been lucky enough to secure in Egypt and Vietnam and am then hoping to travel on to Singapore or Hong Kong to secure another internship to lead into a full time role in East Asia, as I hope this will provide me with the best experience for my future career.

    At the moment though I feel as though I am facing two kinds of risk; the risk of violence and the risk of uncertainty.

    The risk of violence stems from the potentially dangerous situation in Cairo where I will be interning, something that has particularly made my parents worried about my safety. In this context I’m forced to balance the excitement of seeing a country in transition and history in the making, along with professional learning against the physical dangers of the situation turning sour. That balance will have to be monitored by reviewing as much information as possible from reputable sources (such as government travel advisors) as well as speaking to trusted contacts on the ground before making a final decision, shortly before departure date.

    The second and far less serious risk is the risk of uncertainty for me in my future career. Although just starting out, by taking myself to East Asia rather than home in Britain or at University in Sweden to start my career I take myself away from the security of contact networks and recruitment systems that I know about and into a world of business that I do not know anything about.

    Although this uncertainty is slightly worrying, and there is the chance that I will not be able to get a good job, I feel that the risk is worth taking as the lessons learnt in developing economies could provide invaluable in the world of the future, and ultimately would be able to survive as an English teacher before returning to train as something stable but boring, like a trainee accountant.

    I am also hoping to minimise the risks involved by throwing myself into making both business and social contacts as soon as I arrive, something that I feel will be important both in developing my networking skills but also in creating a network that will hopefully help me in the future. Networking that I will hopefully help by improving by language skills when I am abroad.

    The key thing that I think will help minimising both the risk of violence and the risk of uncertainty will be the way in which I build and make use of contacts to help me know as much as possible about future risks but also future possibilities and opportunities. Hopefully making sure that my red alerts don’t stop me from seeing a world of possibilities and green alerts.

    Thank you for the blog and all the articles!


  42. Hello – I’m Joseph.

    I’ve seen the face of adversity many times and have failed while taking risks as well. Those risks cost me my late teens and early 20’s and landed me in over $35k of debt. They were risks where my heart was in the right place, but the money wasn’t. Fast forward a few years later and I’ve paid off all but about 5k of that debt but added student loan debt. There are 2 risks I’m contemplating on taking within the next few months, but risks that I’ve been hesitant to take because I don’t want to end up in that debt hole like before…

    As you mentioned earlier, sometimes you should take a risk on a low paying job if it equals great experience. I took that risk and my savings have since dried up. The experience and knowledge earned is definitely worth it but it’s getting close to the point of diminishing returns. To that end, I’ll be asking for a raise this time next month by selling my worth and everything that I’ve done for the company since my inception here. The risk involved is getting let go, I plan to ask for a 10-15k salary increase. I’m willing to take this risk because I’ll need funding for my app idea that I have.

    Whether I get the raise or not, I’m also considering taking out a loan to build out an app that I’ve had in my mind for quite some time. I’ve wire framed the idea out and it seems pretty solid. The risk of course is that the app doesn’t make any money and I’m stuck in even more debt than before.

    “No risk, no reward”

    Thanks for all of your work.

  43. Howdy, Chris George from Houston here. The timing of this post was perfect.

    I am currently transitioning out of the health/nutrition research field and looking to reestablish a new focused direction in the next 30-60 days. I sincerely value connecting people and see the next two months as a great opportunity to help others and myself. With leaving a field I am passionate about, I had to do some serious risk evaluation. The goal now is to create an opportunity that provides aspects of excitement, change and generosity.

    I thought this comment may come as a risk actually. In truth, I have gained clarity on many of the previous “risks” I thought I was avoiding. After reading the slew of comments from fellow risk takers, I feel truly inspired to use these next 60 days for repurposing my direction and ideas.

    This response, vague as it may be, is in earnest. Thanks for the read y’all!

  44. Hi I’m Krista. I’m an actress and a teaching artist. Years ago I made a resolution to do at least one risk per month, and it was the best year of my life! I decided to continue with that tradition and, to be honest, I have always benefitted from the risks I’ve taken, even if I’ve taken a hit emotionally or financially in the short term. My current risk is to get my acting to the next level. I’ve trained and been in plays, but now it’s time for moving forward again. Even putting a post like this online feels risky for me because I know that when people search my name, they’ll be able to see it. However, how cool would it be if they are searching me because they’ve seen me in a great new TV show or on Broadway. You really do have to push through fear a bit sometimes. People said I was brave when I moved to New York without a job. I tell them, I didn’t allow myself to think about it too much and just did it. That’s the only way the scary things can happen for me. Just move forward.

  45. I will soon be leaving my career in higher education administration at a Midwestern university and relocating to California to pursue ‘riskier’, but more challenging career opportunities. I am a young professional and am not satisfied with my current, ‘stable’ career path.

    The desire to change my geographic location as well as my career path has presented additional risks because both my professional and personal networks are contained to either my current location or current profession. I have been taking steps over the last 9 months to mitigate the risk and reduce the impact of the worst case scenario. These steps have largely consisted of accumulating savings in order to pad any short term loss in income and taking steps to make professional contacts in advance of my arrival.

  46. Hi, i’m Mathias 33, I live in France. I’m currently working as a Business Intelligence Project Manager and i’m still searching for my muse to have more freedom and more time with my 2 daughters.

    – So in the next 30-60 days i really want to quit my current job and to start my own business. But of course, as you can imagine, it looks risky to me to quit my job because i’m also currently planning to build my house and so i have to finance it! Even with my current job it’s far expansive for me…

    – In my case, risks involved in this move is to have more debt and to fail the business i will launch. Anyway, i’m really decided to take calculated risks to achieve my goals. I think risk is every thing you imagine it will happen when you’re going to matters you don’t already know. Uncertainty on actions’ results is something that warns people they’re taking risks. For me, risk is the fear to fail actions taken to achieve my goals.

    Thank you for all these very interesting and valuable advices and case study, it really helps to take action for a better life!

    Sorry for my English, i hope it’s understandable 😉

    Best Regards,


  47. Hi my name is Devon, I currently work as a team member for Whole Foods Market. I love food. I love working and education people about the benefits of eating local and organic food. I’m currently working on putting together an online community that helps educate people and allows them to connect with like minded individuals as well as local farmers and small businesses. I have lived and visited many places in the world and been both a teacher and mentor. I want to share my knowledge and passion with the rest of the world to create a positive impact in the way people eat. I would love the opportunity to pick your brains and learn as much information as I can from you. I hope I have the opportunity to do so.

    “The greatest discovery is the one we’re about to make”

  48. In the next 30-60 days I look to confront risk by launching an e-commerce platform similar to or All the pieces are in place and our marketing strategy is quite seamless. In conjunction with this new business, I plan on switching jobs by climbing down the ladder to an entry level digital marketing position. Although not averse to risk, I am in need of guidance and direction and would appreciate the conversation.

  49. Ben and Reid,

    I don’t envy whoever has the responsibility of sorting through all the posts above. There are so many great, thoughtful stories that selecting just one will be difficult, I’m sure. That being said, I’ll try to keep this as short and relevant as I can.

    I’m trying to transition from public accounting to private equity – I want to be a partner at a private equity firm.

    As you mentioned above, I’d LOVE the opportunity to gain some experience and credibility through an internship or apprenticeship but I’m finding it very difficult to find a mentor and get my foot in the door at a firm…and pay rent at the same time. I know there’s opportunity out there – maybe I’m just looking in the wrong places.

    I’ve already taken a huge risk – I resigned from my “secure” accounting job to work as hedge fund consultant as a way to get some management experience in alternative investments.

    Unfortunately, that fund’s performance has been down and my contract is done, months before it should have been. There is literally no money left. The only reason I found this post was because I needed a break from sending out resumes.

    With all of my “connections” tapped and my bank account basically at zero, those corporate job offers look very “lucrative” right now. But I understand that getting trapped in that system makes me more vulnerable over the long term – I’ll likely remain dispensable in that environment and I won’t be moving in the direction I truly want.

    So here’s the bottom line – I need a motivation boost (and getting some help transitioning into private equity would be nice too). I don’t expect much help until I prove myself and that’s what I want – an opportunity to prove myself to someone who wants to teach me.

    Thank you for reading my post,

    Chris M

  50. Hello,

    My name is Kevin Turner and I’m a 34 year old former teacher and coach from Salem, Oregon. Last year at this time, I weighed 317 pounds. In December of 2011, I decided to change. I changed my eating and exercise habits (some of which I took from The Four-Hour Body) and as of today (June 19, 2012) I weigh 225 pounds. I have lost 64.5 pounds since December and 92 pounds since last year. I started a blog to chronicle my weight loss journey, but as I got deeper into the process, I realized that is what I wanted to do full time. I have seen all of the benefits of being healthier and want to help others achieve this.

    I was the king of feeling like I was stuck and couldn’t change. I was a total self-defeater. Six months ago, I wouldn’t have even entered this contest because there was no way I could win. And taking risks? No way. Too much stress and discomfort. However, as I have lost the weight and started to reclaim my life, I am more confident and have started taking more risks. This has paid off in numerous ways, and this contest is just another chance for me to take more of a risk. I have already decided I am not going back to teaching. I want to transition into full time writing about fitness and nutrition, so I am looking for a job in the fitness world, at the moment, while I work on building my brand and website. I am not a business guy at all, but I am learning. I have been chewing up books (including The Four-Hour Workweek), and trying to learn as much as I can. Winning this contest would be an awesome opportunity to learn from some great mentors. But, even if I don’t win, just taking the risk of submitting my entry is enough of a win. Thanks for you time!


  51. “Now this is not the end. It is not even the beginning of the end. but it is, perhaps, the end of the beginning.” Clever words by Churchill, which I quoted in my doctoral thesis. Chickening out I continued on according to the perfect career layout – but not perfect for me!

    “However beautiful the strategy, you should occasionally look at the results.” Not happy.

    “This is no time for ease and comfort. It is time to dare and endure.”

    I am jumping ship! With two kids and a lot of time invested in education and work, I will finally close the circle and return full-time to what I truly love doing.

    “Success is not final, failure is not fatal: it is the courage to continue that counts.”

    I intend to be brave, and get going – see you out there!

    (All quotes by Churchill. Clever man.)

  52. Greetings! I am Megan, a 31 year old mid-career pivoter, challenge seeker, “Jane of all trades,” and newly designated experimenter in lifestyle design. Inspired by Ramit Sethi, Seth Godin, Tim Ferris, Keith Ferrazzi and others, I am on a quest to find my dream job as well as my muse through systematic research, testing, and natural networking. Below is an overview of how I came to create change in my career, how I looked at the risk involved, and what I hope to accomplish.

    “Chronology of a Cure”

    December 2011 Inspired by the words of Seth Godin and Ramit Sethi, I buy myself a copy of The 4-Hour Workweek for my 31st birthday and am convinced I need to leave my job and start doing things I enjoy before I even reach the first chapter. I try to garner support for my plan by having my husband read the book and also give him The 4-Hour Body for his birthday.

    January 2012 My husband reads The 4-Hour Body first and resolves to lose 35 pounds in 10 weeks, but is not yet keen on me leaving my job. I too get enthralled in the mysteries of The 4-Hour Body and join my husband in “slow carbing.” Cheese is harder to give up than I thought.

    February 2012 With high hopes of rekindling both mine and my husband’s passion for travel and adventure, I plan a short trip to Costa Rica with an overly ambitious itinerary (the closest thing I could get to a mini-retirement at the time).

    March 2012 After 10 weeks, I’ve lost 7 pounds and gained muscles where I’ve never seen muscle definition (and I’m athletic) and my husband has lost 37 pounds using the methods from The 4-Hour Body. We venture off to Costa Rica and my husband finally reads The 4-Hour Workweek. Sometime between zip-lining, water sliding into hot springs and reaching the top of the Cerro Chato volcano, we come to the agreement that I should leave my job and perhaps we should live abroad.

    April 2012 Second thoughts about leaving my job begin creeping in. My husband reminds me to ask myself “what is the worst that could happen?” A thoughtful and honest analysis again reveals that the potential benefits of new opportunities far outweigh the costs of remaining in my current position. I develop an action plan with specific goals. We won’t go broke and I can be happy, productive, and fulfilled. Risk and reward analysis complete and plan of action drawn out, I make the final decision to leave behind my “secure” government job and give notice.

    May 2012 I celebrate my last day on May 4th almost exactly 3 years to the day that I started the job (it’s no coincidence, I gave myself an ultimatum). I use techniques from Ramit Sethi’s 30-day course on hustling your way to success along with the lessons from his dream job course to secure an interview at a winery I love, less than two weeks after leaving my job.

    June 2012 While awaiting a part time job proposal from the winery, I secure a freelance role as a researcher for a new book under development about people in the world who have used their voice to make a difference in society. It turns out that the author and his wife were inspired to leave their jobs of 20 years after reading The 4-Hour Workweek. Neither position pays much, but both offer amazing opportunities for learning and connecting.

    I continue to research potential dream job roles and companies through natural networking. I turn to the words of Keith Ferrazzi to remind myself that I must be “audacious” in my pursuits. My goal is to obtain at least 3 dream job offers by the end of July while also developing my muse idea per The 4-Hour Workweek.

    Tim, I’m starting to see that promised land you talk about. Thank you for the directions!



  53. Gentlemen,

    As many have suggested, risk is relative to timing and circumstances. As I started writing this post, I was employed as a remote member of the executive management team. Between that start and now (couple of hour window), I have been informed that I am no longer a member of the team, and have a role only as an outside broker. So I was certainly exposed to career risk and now need to determine with much greater consideration to timing a career change.

    As a teen, I grew up with a belief that I would run companies, be a deal maker and keep track of success via Lucite tombstones and bank accounts with billions.

    Successful through college and in my initial corporate role with Kinko’s, I continued to feel I was on a path towards my goal. After several positive years with Kinko’s in which I learned field operations and lead projects at the corporate level, I attended UVA’s Darden School to earn my MBA.

    My BHAG (I studied under Jim Collins and still regard Built to Last as one of the best business books ever published) of financial success was now supported with the education, tools and experiences that should have formulated a path to goal achievement.

    Further through time, I have taken risks, traveled the world, moved in pursuit of new career opportunities, and have been part of multiple start-ups along with the resulting melt-downs. Looking back now, with my fortieth birthday in the rear view mirror, I have achieve great success at home, in growing a family and raising my children, but the one thing I have yet to achieve is something resembling my early dreams and ultimately refined BHAG of creating a self-directed path that would yield the type of success or results I envisioned early on.

    As noted previously, I have just has a major change in my employment status. As such, in the next 30 days I plan to leverage my network, connections and current efforts to earn an offer in a new firm and fully commit to a new role. Several current contacts present opportunities; all of which could lead towards achieving my financial goal. While these opportunities all are positive and could yield strong returns, my next goal is diversification. This may take more than 30-60 days, but as a secondary goal to the short-term change, I am looking to find a way to rebalance my career portfolio. The concept is to fully fund my new position with energy, creativity and good work while at the same time finding time to build my network so that I have a constant source of new opportunity t

    My one major constraining negativity bias is towards any sort of relocation (for now). Travel – fine. Living on the road – less so. Moving – not really an option. I love it here (Southern CA). My family is here; kids are heavily engaged in sports, their own peer networks and their academic paths. So in terms of risk, I just dramatically ratcheted up the challenge of finding a new role locally or one that will support another remote member of the team.

    Thank you for your consideration.

    Best regards,


  54. I thoughtfully made this short & sweet for you guys:

    Intro: Caitlin. 27 years old. Currently working at an Ad Agency from 9am-8pm (which is even BETTER than your typical 9 to 5, in case you were wondering!)

    Change I Plan to Make: Quit my job in 32 days to volunteer & travel in Peru and Costa Rica, blogging along the way. End goal is not only to gain invaluable life experience, learn a new language, help those who need it, be free from my desk, & live the life I’ve always wanted to lead – but I’m also focusing on determining a way to employ myself while also helping others. I have my work cut out for me and could definitely use a little guidance (wink, wink).

    The Risk: It is riskier for me to NOT make this change than it is to make it. I plan to “remain fearless” and not just because that is the name of my blog.

    Thank you Tim for another inspiring post, as always, and double thanks to Ben & Reid for offering their help!

  55. Mr Casnocha, Mr Hoffman, I’m going to let you into a secret. The change that I envisage is so drastic and unnerving to both myself and my family that I haven’t told a soul. Not until this point. My parents have no idea about it, and I’ve only just given myself permission to entertain this scheme in its entirety. You see, I’ve been scared of dreaming*. And I know that you can relate to this fear and vulnerability. It’s what makes us human.

    *In this context, dreaming means completely letting loose and giving oneself liberty to think up wild and wonderful ideas and plans; the best form of dreaming in my opinion.

    So, let me tell you about the dream of this twenty-six year old receptionist…………………..

    I want to meet the world’s greatest English-speaking orators so that they can help me prepare and practice for a 15 minute speech for a TED conference in the USA.

    I then want to tour primary and secondary schools across the United Kingdom, talking to school pupils about public speaking, found a number of speaking clubs for under-privileged children under the age of 18 and produce an online course and DVD about this subject, which has been abandoned by all but a few very expensive, elite schools.

    After that, I want to go on a semi-world tour by sea; think Old World aristocratic Grand Tour, meets seafaring Herman Melville, with a touch of Eastern Odyssey à la Lord Byron, without the debauchery and decadence, and more of the high culture and language learning. Mororcco, Turkey and India would all be on the itinerary. All the while I would keep a travel journal, and at the end of my tour I would write an eight-page piece for National Geographic, (my favourite magazine).

    So, what are the big risks? Well……………

    1.I might get kidnapped. I might get mugged. I might get snatched away and sold as a slave. I worry about travelling on my own as a woman who is often mistaken for a teenager.

    2.Emotional/psychological risks: I might have a panic attack in the middle of nowhere and have nobody to help me.

    3.I have a fear of the open sea (maritime agoraphobia?), I have an acute fear of big ships and anchors, get sea sick and anxious if I can’t see land for a long time.

    4.My ego/pride: I have had no notable speaking experiences to date. I dislike the sound of my voice. I might get stage fright at the conference, start stuttering, forget my words, and panic at the TED conference.

    5.My family might be totally against this idea. I would risk loosing their support and this is my biggest fear.

    6.I will be leaving my current job and lifestyle and stepping into the great unknown. Having read your article, however, I think that staying in my job and going about things the usual way is the riskiest thing that I could possibly do.

    The point of this plan is not to go gallivanting across the globe, living a hedonistic lifestyle and then showing off about it afterwards. I want to show people who are in the same situation as me, (shy, semi-reclusive introverts who are stuck in a rut) that actually, they are perfectly capable of coming out of their shells, surprising themselves, and taking a few well-considered risks.

    I would love to have this opportunity of having the two of you as my mentors because you are both such inspiring people. I hope that you enjoy reading all of these ideas, and have an absolutely brilliant time mentoring whoever you finally choose. I will let you know how my story pans out anyhow.

    I thank you both for taking the time to read my message.

    Special thanks go out to Mr Timothy Ferris, for yet another outstanding article. I remember you saying in an interview that you wanted to love, be loved, and never stop learning. I agree that these are among the most important things in life.

    Peace and love,

    Ntongo Kiwanuka (Miss)

    London, United Kingdom

  56. Reid Hoffman Mentorship Competition

    Mr Casnocha, Mr Hoffman, I’m going to let you into a secret. The change that I envisage is so drastic and unnerving to both myself and my family that I haven’t told a soul. Not until this point. My parents have no idea about it, and I’ve only just given myself permission to entertain this scheme in its entirety. You see, I’ve been scared of dreaming*. And I know that you can relate to this fear and vulnerability. It’s what makes us human.

    *In this context, dreaming means completely letting loose and giving oneself liberty to think up wild and wonderful ideas and plans; the best form of dreaming in my opinion.

    So, let me tell you about the dream of this twenty-six year old receptionist…………………..

    I want to meet the world’s greatest English-speaking orators so that they can help me prepare and practice for a 15 minute speech for a TED conference in the USA.

    I then want to tour primary and secondary schools across the United Kingdom, talking to school pupils about public speaking, found a number of speaking clubs for under-privileged children under the age of 18 and produce an online course and DVD about this subject, which has been abandoned by all but a few very expensive, elite schools.

    After that, I want to go on a semi-world tour by sea; think Old World aristocratic Grand Tour, meets seafaring Herman Melville, with a touch of Eastern Odyssey à la Lord Byron, without the debauchery and decadence, and more of the high culture and language learning. Mororcco, Turkey and India would all be on the itinerary. All the while I would keep a travel journal, and at the end of my tour I would write an eight-page piece for National Geographic, (my favourite magazine).

    So, what are the big risks? Well……………

    1.I might get kidnapped. I might get mugged. I might get snatched away and sold as a slave. I worry about travelling on my own as a woman who is often mistaken for a teenager.

    2.Emotional/psychological risks: I might have a panic attack in the middle of nowhere and have nobody to help me.

    3.I have a fear of the open sea (maritime agoraphobia?), I have an acute fear of big ships and anchors, get sea sick and anxious if I can’t see land for a long time.

    4.My ego/pride: I have had no notable speaking experiences to date. I dislike the sound of my voice. I might get stage fright at the conference, start stuttering, forget my words, and panic in front of all the confident and successful Americans.

    5.My family might be totally against this idea. I would risk loosing their support and this is my biggest fear.

    6.I will be leaving my current job and lifestyle and stepping into the great unknown. Having read your article, however, I think that staying in my job and going about things the usual way is the riskiest thing that I could possibly do.

    The point of this plan is not to go gallivanting across the globe, living a hedonistic lifestyle and then showing off about it afterwards. I want to show people who are in the same situation as me, (shy, semi-reclusive introverts who are stuck in a rut) that actually, they are perfectly capable of coming out of their shells, surprising themselves, and taking a few well-considered risks.

    I would love to have this opportunity of having the two of you as my mentors because you are both such inspiring people. I hope that you enjoy reading all of these ideas, and have an absolutely brilliant time mentoring whoever you finally choose. I will let you know how my story pans out anyhow.

    I thank you both for taking the time to read my message.

    Special thanks go out to Mr Timothy Ferris, for yet another outstanding article. I remember you saying in an interview that you wanted to love, be loved, and never stop learning. I agree that these are among the most important things in life.

    Peace and love,

    Ntongo Kiwanuka (Miss)

    London, United Kingdom

  57. I have taken career risks all my life, focusing on the benefits of an immensely eclectic skill set that I have developed by working in many different fields. This led to my biggest risk to date, building my business, BizBang LLC. I emptied most of my savings and quit my other two jobs to focus all my time and energy on BizBang. So far it has been the biggest…now on to bigger risks. My company has incorporated, I have bids out on Elance ala 4HWW for my web design and it should be complete in 3-4 weeks. I even have clients lined up, now on to the risky part. I have just purchased an RV and will end my lease at my home to allow me time to 1. Travel and work at the same time, 2. Better facilitate my customers by being able to come to them and spend better face to face time with them while I build the business, 3. Eliminate rent from my budget. The risk in this comes from going from a grounded brick and mortar office and throwing myself into a world of mobile officing full time and to the unknowns of doing business on the road. I know many salesmen work in outside sales but I know of few people that are fully mobile in their businesses. I am confident that my history of diverse employment and general “cockroach in a nuclear bomb” demeanor (Nothing can kill me). Will help me to persevere. That and the assistance that Tim Ferris is going go give me for my well worded response! <———

  58. Everything is arbitrary (…and why it matters).

    Why do we do what we do?

    We act in order to survive and replicate but the strategies that we pursue to do this are, essentially, arbitrary. The way that we explain things is arbitrary – it could have happened for many reasons. You and I will not see things the same way because we have be shaped by different experiences. We will attribute causality in different ways. We will seek evidence from different sources. We will have different emphases and biases. Was that luck or skill? Was that success or failure? Is it safe or risky?


    Imprints are important to shaping the way we behave – the experiences that made us who we are along the way. These are the anchors that we use to make decisions based upon, they are the ‘factory settings’. They also determine the way in which we think and we act based on emotional responses (even if we like to think we are rational). These can create thinking traps – the thoughts that hold you back, that force you to bite your lip and wait and the words you use to justify your limitations. Or imprints can set you free. Jay-Z was just an average schoolkid until his 6th grade teacher told him he had a way with words. What if she had bit her lip and never spoken? How would the world be different?

    Imprints too are just arbitrary events that have shaped you along the way. This raises the question: who are you? If your personality, your beliefs and your thoughts are shaped externally then is there an authentic you? Would you still think the way you do if you had caught that train, had spoken to that girl or had taken that risk?

    Similarly if you aren’t who you want to be then you can change things. You are plasticine in your own hands that you can mould, if only you realised.

    Shape your world, do not be shaped by your world. And if you manage this, you owe it to the rest of us to tell us how to do the same.

    This is why defaults and social norms are so powerful. They imprint the path to take and affect our behaviour in ways we may never fully realise. Take a simple thought; Times New Roman was for years the default font of choice. What if the decision had been to go with Calibri or Comic Sans, how would the world be different? We know that your imagination responds better to the colour blue than black, how would the world have been different if everything was written in blue? The decision as to what font to use as the default was (probably) arbitrarily decided but this may have an effect on the way we behave, the way we think and the lives we lead.

    Consider this; the organ donation rate in the United Kingdom is about 17% whilst the organ donation rate in France is about 99%. Why the difference? A stronger sense of solidarity within the French Republic? Or British rational self-interest?

    How about simply the difference between an opt-in and an opt-out box on the form that you fill in when you receive your driving licence? No doubt this default was decided arbitrarily one day by a person who will remain anonymous but their decision on that day inadvertently resulted in a shortage of organs within the British health system whilst another decision has lead to a plethora within the French. It shows the extent to which we follow the road most travelled.

    Why not change the default option then? Why not indeed. Yet changing the default is often a big dilemma, only because something existed before. “You can’t change it to blue, it’s always been black”. “You can’t take away my organs, that’s deceitful” “You can’t become an entrepreneur, that’s madness”. How would our behaviour and our imprints be different if that wasn’t the case that some things are arbitrary like this? If the opposite were the norm?

    Ultimately the path in life that most people choose is arbitrarily decided based upon the decisions of people they will never meet and who will never be affected by their actions. Going to school and learning what you did is arbitrarily decided. Why maths and not meteorology? Why english and not emotions? Passing tests, getting in to college, going to work is arbitrarily decided by the ‘factory setting’ of the world we live in. It has developed from a default. And most people follow the default.

    But the saddest thing of all is that most people never realise this…

    Now how do you respond to this? Does this give you a feeling of ultimate fear or ultimate freedom? Because all I’m really saying is: there are no rules.

    Do you agree?

    I am sure that most people will disagree, but you aren’t most people. Most people accept their circumstances and will never test my theory. Maybe I am wrong, maybe there are some underlying rules to the world. Maybe. But nobody can prove me wrong without first trying to push their possibilities beyond those of everyone that has ever lived. Why not try it today? It doesn’t have to be anything earth-shattering. Everything was once just a thought but it’s these small thoughts that can change everything. Just try to test a few rules that you think you have to abide by.

    What will you test first?

    [NB: I didn’t follow the brief on this one because I knew that everyone would – that’s the default option to take. But isn’t that the lesson to lifestyle design? There is always a backdoor option if you look hard enough. I do have a plan for the next 30-60 days, a big one, and I’d love to discuss it with you.]

  59. Gentlemen,

    My name is Todd, and I am in the non-risky career of healthcare….seeking career risk, against the norm.

    I want to spend less time in the hospital and more time with my wife and new baby. I see opportunities, and, strangely, the more successful I am in my ‘career’ the more uneasy I’ve grown with my sense of risk and personal development.

    Now, I’ve followed my dreams in the past, and even if I’ve made errors, I have always landed on my feet. I have learned from these experiences, and somehow during those times, as hard as they may have been, I have been able to remain focused on the goal. So what has happened to the guy that drove so hard to be where he is today?

    Have I lost my professional mojo? My hustle??

    Or is it that my interests don’t jibe with my employer’s ideas of what my interests should be?

    I have come to the realization that the things that I want – more time with my family, more time developing my entrepreneurship-skills – that those things mean nothing to my employer. To me, that is the impetus to accept and seek risk, in order to avoid the staid line of workers filing-in, one by one, into the cosmo demonic healthcare shackle.

    I’ve begun lifting my own spirits out of demoralization and seeking the opportunities that will allow me to not only expand my knowledge base, but to allow me the time to pursue my entrepreneurial endeavors. To work less, for more money. To be fully independent of, ‘the group,’ the supposed ‘safety’ of the hospital.

    To have the opportunity left up to me.

    To take the chance, to risk, and ultimately, to have the opportunity to remember what it is like, to know, that I will land on my feet.

  60. I would love to launch my own company, but the negativity bias for me is amplified by being the sole source of income in my home for a wife and two small children. It is difficult for me minimize that level of risk using a rational approach.

    On an unrelated note. Mr. Hoffman, I would love to see LinkedIn leverage its platform to target a slightly different customer segment, namely entrepreneurs. is interesting, but the platform pales in comparison to LinkedIn. I could see a matching and team building site, with dating site type metrics, and the communication mechanisms of a LinkedIn as a powerful tool to help form teams and startups that could change the world.

  61. This opportunity sounds amazing! Ben and Reid, I am going to tell you why your gracious mentoring will also benefit you.

    Why would you go there? This is a common question that American travelers hear from their own countrymen when traveling to the lesser-known parts of the world. For those who have traveled to the Middle East, Central Asia, or even parts of Eastern Europe, I’m sure you can relate.

    Traveling to these places is typically looked as risky. But like entrepreneurship, mitigated or thought out risk quite often results in outstanding treasure. And often times when that risk is explored, it becomes evident that the initial perceived risk wasn’t all that risky to begin with.

    In the next 30-60 days I am going to:

    -Continue pitching my idea for a global travel TV show—we shot the pilot in the Republic of Georgia last year (all self funded)… absolutely stunning! I’d love to share my three-minute trailer with you both.

    -Network my face off

    -Work on setting up an interactive website

    -Continue gathering a worldwide following

    My goal is to set up a business that educates (and doesn’t preach) to an American audience about the world away from the news headlines.

    Why is it that when The Republic of Georgia is mentioned that it is usually surrounded by five negative adjectives? My theory is because most of the information that comes out of a place like the Republic of Georgia is negative; therefore, nothing is countering or balancing out the news that’s captured conflicts of the past. Bombings in Madrid or London don’t scare the average traveler because we see other positive images of these places. Unfortunately this reality doesn’t work for a large portion of the world.

    My goal it to change the typical “Why would you go there?” with “That’s awesome you’re going there!”

    The US has so much going on, but in many ways it’s quite removed from the world My goal is to start a movement that changes this reality.

    And why will this benefit you both? Because if you are interested in the world, this movement is only going to make it a better place. And who doesn’t want the world to be a better place? (Yes, I know, many don’t)

    I am looking for assistance in refining my objectives and building a brand. Thank you for your time. I wish to talk with you both in the future.



  62. Great post. Fun concept, this negativity bias. And although not mentioned in this post, I find that this challenge is relevant in life & love.

    I understand the first 2 parts of the negativity bias, overestimating threats, underestimating opportunities, but I don’t understand how to overcome the third aspect underestimating resources. Does this also relate to ones own self-worth? It seems like it would.

    I took the dive almost 2 years ago, and started It’s doing well. Bootstrapped and growing slowly. But every day I start my morning thinking how do I spark rapid growth? How do I go from the 30 something clients, to 300. HOW do I scale? I enjoy reading. I try to “read” my way to solutions. But I haven’t come across anything to help me achieve this. I don’t expect it to not be hard.

    There’s two aspects. The internal aspect of growing the resources and expertise. I know I can do this with some dedication. Growing our internal knowledge base. documentation, and training is something I can outline. But growing the external aspects of revenue and maintaining that growth I’m lost.

  63. This post was great. It caught my eye after reading about Reid in Wired a few months ago.

    For my 9-5 work, I have a dream job – I get to go all over the US meeting researchers in robotics, unmanned vehicles, and almost anything really cool you can think about – and I meet with passionate educators in academia – selling engineering research and teaching experiments. I’ve really lucked out.

    My dilemma is that I don’t own my time and I’ve been exploring ways to ween myself off of a paycheck. This exploration has sometimes been painful – perhaps setting me back years financially. I really didn’t manage my risks properly in the past.

    Over the course of many failures, I’ve learned to mitigate risk through the Four B’s (I just made that up): Bootstrapping, Bargaining, Bedazzling, and Bartering. For me, it’s now really apparent that one needs to fail repeatedly without destroying oneself. The financial cost (emotional I can still handle) of these failures is getting smaller and smaller so I can pick up and try again after a failure.

    So what’s the 30-60 day plan? I’ve been working for over half a year on a Kickstarter campaign that’s set to launch. This would fall under the category of “An opportunity where the risks are highly publicized.” This is now going to put me out in front of a tech-savvy crowd and the risks are:

    – Getting eaten alive with negative feedback

    – My dream job being taken away for me not being focused (or sales dropping)

    – Not being able to deliver on the commitments I’ve made to the KS community

    – Being blacklisted from any fundraising, whether crowd sourced or VC

    – Alienating friends and family by having this project consume me

    When I look at these, I’m trying to differentiate between which are fears and which are genuine risks.

  64. Awesome post, in line with your fantastic book.

    In the next few weeks, I’ll be driving across the country to transfer to a new job within my current company. I’ll be shifting away from federal clients into tech sector work, living in Los Angeles and commuting to the bay area and pacific rim countries during the week.

    I’m also going to be getting my MBA part-time at USC, with all-day Saturday classes to allow for the client travel during the week.

    Certainly risky, probably a lot to take on, but it’s a career pivot, while sticking in that permanent beta mode, learning as much as possible. Right in line with your ABZ planning, it’s a calculated risk that has limited downside but creates so many opportunities.

    Interestingly enough, the transfer almost fell through, and following the traditional HR/talent transfer process didn’t work. It took a network, a friend and colleague I knew from California to put me in touch with his leadership, then a subsequent serendipitous meetup here on the east coast to make everything happen.

    Your book has already helped my career more than I could imgaine. Thanks!


  65. What change do you want to make in your career…?

    I want to accept a revolutionary offer in my business (I´m freelance in the field of home automation), but this offer is more related to all my experiences overseas than actually my experience in the technology itself. A guy wants me to support him to move

    his company from Spain to South America. Even though it´s a company related tomy market, he likes me because I´ve been working in Spain, Ireland, South Africa, Seychelles (this post is signed from Victoria, Seychelles) and I got large experience with

    work permits, cultures, clients. I´ve been pivoting from installers to distributors and manufacturers (I risked salary for learning). What it was a risk (move to South Africa) some time ago on the eyes of my family and friends, now it´s an opportunity (different banks accounts in different currencies, experience in different countries and international business…)

    If I accept this offer, I will change the cuore of my business ( and the main goal that I got in mind.

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

    I´m thinking about this risk as I´ve done with all my previous risks (and what has become the motto of my life, and what I´ve been teaching to all my friends and family, and what is the main pilar

    of the blog I´m starting http://www.sabbaticae.comfocused to sabbatical retirement as a powerful tool to boost your life):

    Make decisions and movements when everything is going right, and not when your only option is to make a decision (because everything in your life is wrong).

    When everything is bad, you don´t have options, you are at the bottom, you need to get out, your next movement won´t be smart.

    When everything is perfect, it´s difficult to make a change, because you think that you are risking too much and all your effort, but the truth is that ONLY THEN you are plenty of ideas and momentum, so a bad step can´t take you out of the game,

  66. I certainly know a thing or two about risk. I’m writing this from a hotel room in Nigeria where I’ve been spending the last week trekking through jungles, fording rivers, navigating death-highways, etc, all to evaluate a few mining prospects. It is my job to understand how prospective things look and weigh that against what inherent risks are involved, be they project, political or market risks. I do, as a human, fight the urge to play things too safe, but I also think it is possible to swing too far one way and start taking poor, uncalculated risks and jeopardize stable and well-paid, albeit boring, opportunities.

    Let me rewind a bit…

    Three years ago I quit a well-paying job in the world of investment banking in London to return to my home country of Canada to work with early-stage resource companies. That decision was very much one hinged on the fact I was bored with my job and while it is a lucrative one, relatively, I wanted to be where the real action was. I’m admittedly able now to view this decision with a lot of hindsight clarity, but I’m not sure it was the right one. The last 3 years have been very educational, but also extraordinarily trying financially. Presumably the goal of any entrepreneur is success and to see that manifest in wealth/income, and it’s sometimes hard to see the light at the end of the tunnel. Taking these low-paid ‘educational’ ventures on only works if you can turn that education into something meaningful later, or to put it in business speak, if the present-value of the increase in future earnings you’ll see is more than what you are sacrificing currently. In the last 3 years combined I’ve earned less than half of what I made in my final year as a banker meaning I’ve put myself into a big opportunity cost hole to chase these risky dreams.

    Right now I’m faced with the decision to either scurry back to the comfortable world of high-finance or press on with entrepreneurship in the resource world. I fear that the threat of personal bankruptcy may force the former, but I’d love the chance to talk to some other people experienced in these matters about this.

  67. I want to finish the negotiation for a position in my company where I will ultimately have a new business built around me. I’ve been thinking about the risk relative to the risks I’ve taken in the past, and I’m realizing that the risk itself is probably much smaller than I would have ever imagined.

    I started out by becoming a Microsoft Certified Trainer at 18 and living in hotels more than my own house for a few years. I made the concous decision to start my career by teaching instead of attending college. I figured that useful certifications and real-world experience were my best choice. After 3 years, I was able to complete my contract term and become a fully independent trainer that earned 100% of my billings. Eventually a company I did a lot of teaching for moved me to my current home and hired me on full time. I accepted a ton of risk very early in my career before I knew what I was doing.

    I got heavily into Skydiving with a co-worker there. This taught me a ton about calculated risks, as my life was on the line every time I jumped. Ultimately, I ended up in a relationship with 2 little ones that changed the context I was living in and made that risk personally unacceptable for a while in my life. Another huge risk that makes my current choices seem small.

    My career decisions haven’t been as risky as hurling myself out of an airplane, but for some reason I’ve found that more variables are at play. Decision paralysis has been a struggle for me. Having more options hasn’t made my decisions any easier, and has sometimes kept me from making any decision at all. I’ve currently chosen stability and flexibility in my career over huge wins, but lately I’m realizing that I can absolutely have both and still manage an acceptable amount of risk.

  68. Hi, i’am à french student with american nationality.

    For 1 year now I’ve been studying in an engineering school in the suburb of Paris and in the same time starting my own project on the side.

    I understand that our enemy has two faces:

    – the first is our inner fear of the risk, because it prevents us from taking what we feel being a risky action.

    – the second our bad evaluation of the beneficial outcome of a risky action.

    I also grasp the idea that our judgment of the fear/of a beneficial outcome

    Depend on the

  69. Dear Tim, Ben and Reid,

    In the next 30 -60 days, I would like to at least have a commercialization plan worked out describing the pathway to introducing one of my new product ideas to the market. Ideally, I will have acted on some of that plan too. I have been sitting on this for awhile – simply because I don’t know where to start (see all my questions below).

    I am a very busy working mother who on more than one occasion has been called an efficiency freak. Efficiency is my passion. Whether I am doing laundry, helping my kids study, looking for the fastest driving route to work and back, or learning about computer programming, I look for the most efficient and cost effective way to achieve every task.

    My new product ideas arose from that perspective. I wanted to find a way to help alleviate the dread of two of the most common recurring household chores every household around the world faces every day. I searched on the internet and – to my knowledge – there is nothing available for sale that is even similar to my concepts. I see many people asking for tips on how to do these chores better, but the advice isn’t particularly helpful. While my products won’t solve the problems 100%, I strongly believe they definitely make these daily chores significantly more pleasant and manageable, and potentially have some extra benefits for the whole family. These products will be valued.

    One product is very low-tech (I made a prototype of this one, and plan to make a few and do a pilot test on it with some of my friends), and the other is an app that requires some hardware too – so I need more guidance on this one. Neither of these products carries any risk of personal injury – a big plus.

    Now, the risks – as I see them: I will speak to the low-tech idea as the risks are different and easier to identify. I think the biggest risk is someone copying my idea as it is very easy to make (I can’t believe no one else is doing this!). There are definitely companies out there with established manufacturing and distribution channels and retail contacts that could easily dominate the market much more quickly than I. So I need guidance on this. Should I simply meet with these companies, and try to negotiate a license to my idea in exchange for a royalty? What is a reasonable royalty rate? If I should bring the product to market myself – I have no experience manufacturing and bringing a product to market – how do I know that others will agree that this is a good idea and buy it? Do I have to do some research before I commit resources? How do I arrange large volume manufacturing? How do I determine how much to manufacture? Is this a product that I should sell on-line through my own (still to be created) website, and market and promote it through social networking, or should I pursue larger retail outlets with my idea and prototype– like Wal-Mart and Target – and try to negotiate purchasing contracts with them. I think these companies would love this idea and want to sell it, and it would be easier to sell to international markets this way.

    Also, do I need/should I file a patent application (considering that I, personally, don’t have the means to enforce the patent – but would a company want a patent app filed in any case)? If this product is not patentable, how do I protect the idea? Will I be infringing someone else’s patent (I did a patent search but don’t have the expertise to evaluate those patents against my idea). I need time to dedicate myself to this business. How much time do I need? With respect to the various commercialization pathways addressed, what is the timeframe for getting a product on the market. What resources will I need? Do I need a bank loan? Should I ask for reduced hours from my supervisor? Quite honestly, if this product is successful, I would be very willing and happy to switch careers and pursue this line of business.When will I know that I should give up – that it’s not working? Thanks so much for this opportunity, looking forward to hearing the outcome of the competition.

    Regards, HFF

  70. My name is Seth Rogers. I am 20 years old. In the next two months, I will be quitting my part time job to focus on idea a friend of mine had. The idea itself is not as important as the risks we will be taking to pursue our new business in the app world, as neither of us has any real prior experience in our selected field. I don’t have a plan yet, or a fall back idea, only my savings and a passion for perfection. As well as actually getting a business off the ground, I am finally moving out from under my parent’s financial umbrella and will be paying for all of my living expenses myself. Essentially, if we do not see a return on investment within two to three months, I will have to move onto other projects, and probably beg for my job back.

    So in the end, I am risking my life’s savings, my friend’s life savings, my parents respect and confidence, my pride, and a very important friendship… Oh yeah, I’m also goin to continue my junior year at UT Austin this fall. Nervous? Not a bit.

  71. The career move I’m looking to make is re-starting my Sales consulting business. It’s something I pursued full-time for the first half of 2011 and put on hold when I took a Sales Management position with a company I wanted to join.

    Right now the position I have is something I want to do. Long-term I want to be doing my own thing, and instead of trying to get it going as my full-time job right now I’d prefer to build a client base on the side to figure out exactly what it is I want to do consulting so when I make that jump I’m in a much better place.

    I’m generating plenty of ideas. For ways to offer my services, I want to do only one thing right now but offer different levels. For product ideas, if I can perfect what I’m offering as a service down to a system I can then sell it to people who would rather pay less and DIY than get my expertise.

    The risks? Time is tight and I’m concerned I won’t be able to either get business or be able to handle it. I have a newborn at home, and I more or less have an 8-6 job, so I don’t have tons of free time kicking around. Thankfully my job aligns with my consulting, so if I get better at my job it converts to my consulting. Still, the last thing I want is to spend my free time building this only to realize I need even more time to make it work properly. Finding the right offer, the right way to get it out there, and then deliver is my number one concern.

    Second risk? While my employer hired me knowing I did this kind of work on the side, the last thing I want to to is do anything to lose this job right now. It’s great experience, a great paycheck, and in line with my long-term vision. Balancing the two is crucial to me.

    Book looks interesting, definitely considering making it part of my required reading this summer!

  72. Interestingly, I actually found this blog post last night while debating whether to contact Reid directly. Jeff Bussgang and Guy Kawasaki certainly speak highly of him in their writing and since he was an angel before joining Greylock, I thought that just maybe he would respond to an inexperienced and determined young man’s cold email. By coincidence, this blog answered my search. Thank you Tim, Ben and Reid.

    My name is Anders LaScala and I am 22 years old. I just graduated with high honors in chemical engineering from the University of New Hamshire, in my home state.

    Simply put, I am going to attempt to create a new computer game. The game is not so much the result of my creativity as it is a response to an open niche in the market. Someone will soon fill this niche, but I believe that with the help of two highly experienced players and our very strong community support, we can fill it most effectively.

    The situation is this: There is no existing MMOG that explicitly addresses the demands of the avid player versus player (pvp) enthusiast. The current thinking against basing a game on pvp content is that it will limit the size of the customer base by not appealing to everyone. While this might be true, I believe that there are more than enough customers for such a game to be quite profitable.

    Indeed, look at the recent success of Riot’s League of Legends (LoL). While the style of pvp in LoL is different from what I am considering, the concept of communication and skill on a level playing field is what makes the game fun and challenging.

    Existing MMOGs are filled with monotonous leveling, grinding and gearing, which make them more frustrating than challenging. These games do provide some pvp combat, but mostly in the unorganized form of battlegrounds. Blizzard’s World of Warcraft (WoW) comes the closest to the mark with a competitive 3v3 arena style of game-play, but it is very far from being adopted as a true eSport at Major League Gaming events. However, it is still WoW that current arena enthusiasts are trying to twist into providing the game-play they so enjoy. Furthermore, Blizzard has stated that WoW will never cater to the pvp enthusiast.

    Both of the two players on board with the new game idea have strong ties to the overall community, although we have decided that it is too early to sell the community as a whole on the new idea.

    The players are:

    Byron (Reckful) Bernstein

    Byron is actually responsible for the majority of pvp balance adjustments to WoW over the past 4 years (behind the scenes and without any compensation) before quitting the game in late 2011. He is the most well known US player and lives in Los Angeles.

    Ryan (Hydra) van Buiten

    Ryan started the popular gaming blog Hydramist back in 2008. He is well known across the gaming world, especially Europe, for his priest play and lives in the UK.

    Down the road, the community will likely become invaluable as a marketing tool for the new game. This is because the community consists of highly dedicated players who would love for this type of game to exist. As a group, they have actually created a homemade spectator UI and have recently put together player-hosted tournaments that are live-streamed for their online audiences and have only minuscule rewards for the winners. (Live-streaming refers to providing aspiring players and fans with a means to watch how they play and listen to their Skype conversations in real time.) Additionally, many members of the community live-stream on a nightly basis to earn a living from the commercials that appear on their streams. On average, each of these streams has between 200-2000 people watching at any time, and when combined with how active the players and audience are on the message forums, this could provide powerful word of mouth marketing.

    As I mentioned earlier, I am fresh out of college and have no experience producing games. That said, I’m an eager student and might fit under the category of “someone with little relevant experience but high learning clock speed.” I have nothing holding me back and am willing to do whatever is best for the game, even if that means stepping aside as it begins to grow.

    I have read extensively on the subject of game design recently, so I have an idea of the process, but I am in sore need of an advisor who can help make introductions, hire ‘A players’ and help build confidence in our team. Above all, we will soon need to find an excellent and experienced technical director (essentially a lead programmer) to help write the technical design document. The good news is that the beginning pre-production stage of building an MMOG consists of mostly documentation and preparation, which is best done in a small team of 5 members at relatively low expense.

    I would like to end by touching on the risk and societal benefits of this idea. The risk is that I am under a lot of pressure to find a job in the chemical engineering field from my parents, even though I simply don’t find those jobs very exciting. I was lucky to graduate without loans but do not have enough money to support myself for long (I’m currently staying with my sister who lives in Montreal to save on expenses and escape all distractions).

    I want to create this game not because I believe it could turn a large profit, but because people want to play it, including myself. When someone works full time in a city, it can be difficult to find a competitive and social outlet for their energies, and online games that center on teamwork and communication really fill that gap. They don’t literally require much energy, but online friends add color to an otherwise bland day and can be the start of long-term, rewarding friendships.

    I am very grateful for your time and appreciate any advice you might have time to throw my way, even if you are only able to recommend someone else who might be interested in this project. Good luck to all the great ideas in this thread, and again: Thank you Tim, Ben and Reid!

  73. On April fools day I woke up at my new place. I had a new roommate and was headed to my first day on the new job. I had just traded my full time employee position in lue of a contract position. Two months later I took on more risk in favor of staying contract after being offered the position full-time. My reasoning? Balls!!!

    See, I had also started a small business April 1 and it was beginning to take shape. But I needed a push to take it to the next level. I was getting interest I wasn’t expecting in my project and wanted to be forced into making the big decisions I needed to instead of my typical incidental ones. Now that I had some insurance my business idea could be feasible, I still lacked the right approach to make the ship sail. I needed the pressure of a temporary contract to go from my comfy, cooshy, corporate mindset to ultra-risky, hard decision making. All my initial excitement, hard work and discipline I had put into the project was on the line now. I image with enough time and money invested into it, eventually the risk-taking will actually become the lesser risk. Either way, I needed to practice my risk-taking by incrementally taking job security out of the picture.

    I had developed a mental training you can’t get unless you slowly take out the floor beneath your own feet… one corporate carpet square at a time.

  74. I wish I had taken less risk. I have always had a ‘risk-taking’ attitude.

    The first thing you need to do is to become self-reliant.

    People get comfortable with stuff that’s meaningless. I know so many people who make a decent living yet, are completely unhappy.

    Part of this is do to the way we are conditioned in our society- just work hard and you’ll have nice things.

  75. Hi, I’m Jonathan,

    Ben, Reid thanks for a great post. Tim, I’m grateful to you for introducing us to these compelling ideas.

    I really appreciated the way you separated the concept of a career from a single job or profession and characterized it as a self-determined pattern of behaviour.

    The big take away for me was that managing intelligent career risk requires creativity and initiative. These are two skills that I am trying to develop on an ongoing basis; your assistance in this would be invaluable.

    SOMETHING YOU DIDN’T TALK ABOUT that I think would have been a great addition to your post is the role personal values play in developing a career.

    Ben, of all your achievements listed on your blog you say you identify most of all as a learner.

    Reid, you are described online as a “network philosopher” and a living embodiment of Linkedin.

    Tim lives and breathes lifestyle design.

    Evidently these values have influenced your careers and I would like to hear your own experiences and how we can use this to inform our own careers.

    I’m curious about this because this has influenced the career risks I have taken over the past few years: I was a bored accountant and I wanted to do something that mattered to an audience bigger than my line manager.

    After getting the 4 Hour Workweek and some really hard work, I’m now doing a PhD at a world-class institution in an under researched area related to my work experience.

    The end game is to use this to make a social impact that will benefit groups underrepresented in small business ownership because of limited access to quality business support. The huge upside is the potential for social change in line with recent policy changes and legislation.

    Sounds good, but it is risky:

    – Huge opportunity cost, instead of earning in my peak years, I’ve pivoted to something that offers no cash but has tremendous learning and highly publicized risk. Think years not months.

    – There is precious little financial support in my field and it’s taking it’s toll

    To support myself I have held seminars and tutorials for start-ups, these have had small audiences and given me incredible feedback.

    In the next 60 days I want to launch online versions of my most popular seminars for a nominal fee, this will develop my career by:

    – Combining my research and entrepreneurial interests

    – Adding value to a larger audience of new businesses

    – Allowing me to perform my research without financial concerns

    – Support other non-mainstream research (how about lifestyle design topics?)

    I hope you can help, thanks for reading,



  76. Hi Tim, Reid, and Ben

    I’m 22 and I just pulled through a bit of a quarter life crisis.. Here’s a quick rundown of how it happened for me.

    I always had a love for playing music, since I was really young. I wanted to jump right into music after high school, but plain and simple – I couldn’t afford it, and my parents couldn’t afford it. We weren’t exactly a poor family, but my parents were living paycheque to paycheque, always struggling to make ends meet. I figure as much as I’d like to jump straight into doing something I love, I felt the need to support my parents. After all, they’re the reason I’m here today.

    Graduating high school at 17, I jumped straight into a post-secondary technical institute. Long story short, I looked for the shortest program possible that yielded the highest average salary, with the most readily available jobs. That program happened to be an engineering course. (Presumed to be a “low risk, stable” career choice)

    Graduating from the program, I became a building project engineer when I was 20, which is a really young age for such a position. I’m still working the same job right now, but I don’t plan on being here much longer. I mean the money’s great, but it’s amazing how when you’re making it doing something you don’t enjoy, you finally understand what they mean by “money doesn’t equal happiness.” On the flip side, I was really grateful that I was able to give back to my parents.

    Within a couple years into the line of work, I bought a nice car, started saving up for a down payment on a house, and that’s when the crisis hit me.. I asked myself.. I’m 21.. Do I want to be doing this for the next 45 years? Am I going to be satisfied with my life? The epiphany really shook me up. I started reading some self help books and listing out things I want to accomplish, and the steps needed to get there.

    As I was going through this epiphany, the craziest thing happened. I found out that there was one guy who worked for over 30 years for my day-job company, just retired, and passed away 2 days after his retirement. That scared the heck out of me. Work all your life and never get to truly enjoy yourself? I had to make a change.

    Months later, I decided to clear my life of clutter. I downgraded my car, paid off all my loans, and started actually executing things I wanted to do, as well as taking on new challenges and risks. (Still in a smart, calculated sense, of course.. I wasn’t blindly burning money.) Too many people tell themselves they’ll do things “some day.”

    I figure, if not now, then when? What’s the worst that can happen? Sure, I did go through a good chunk of the down payment I was saving up for, but if you want a change, you have to make a change, right? If i’m not happy now, and bought a house.. then I’d just be the same unhappy guy with a house.

    Ridding myself of fears of the uncertain, I jumped straight into executing steps towards my goals. The results have been nothing short of amazing.

    In the last 2 years, I was signed to a temporary music development contract with a record label, got to (and still) work with musicians, artists and writers I never thought I’d meet, started writing a book, and incorporated my own company!

    I also just went to China last month (not knowing ANY Mandarin..) to meet my company’s supplier! It’s amazing how much more you can do by making the tiniest changes in things you thought you needed.

    For the last year, I’ve also been helping people to get their lives “on track.” When people started noticing my “mini successes”, they started asking how I got where I am, and I’ve been trying to help them get to these little achievements as well. I really have a soft spot for helping people going through these depressions, as it can be hard to be taken seriously by your friends. In the next couple months, I plan to help more people steer their lives in the right direction, as well as continuing to build my business. I also plan to continue working at my day job (still need capital) until my business officially gets off the ground.

    I find that almost every move you make for your business is considered a risk.. You’re quite literally throwing your hard earned money at a fire. Whether it smothers the fire or feeds it, you can do all the research you want, but ultimately – there’s only one way to find out.

    This was kind of a quick blurb of everything rushing through my head right now. If there’s anything more you’d like to know, please don’t hesitate to contact me!



  77. Good article. I have often thought about taking risks in life and career in general and came up with an idea.

    My past profession was trading futures and commodities and we had to deal with risk every day. I fully believe that taking these risks with large dollar amounts prepared me for many other life risks (for me moving to Japan was one of them).

    I was trying to help a friend with this very idea and came up with a parallel saying to help him get over fear of taking risks. The idea I call, “Live Like A Trader”.

    It’s pretty simple and involves breaking life down into trading situations so it is easier to remove the emotion from and easier to judge what is best for you.

    Each person has risk tolerance (in trading it is how much money they are willing to lose on any give trade) for their life. The thing about trading is you don’t want one trade to “kill” you. You want to take calculated risks with manageable downside (usually specific levels where the position is exited) and a significantly larger potential upside.

    For example: When I moved to Japan I knew I could always buy a ticket and come back to Chicago and my risk would be the plane ticket cost and having to find a new job, which I felt I could do. The upside was unlimited and I actually had the time of my life because of it and found the woman of my dreams, whom I just married:).

    So, I defined a risk tolerance (some might call this the worst case scenario) in trading it is simply the point where you exit the trade.)

    The point is we want to take lots of risks with undetermined upside and a very determined downside. This way you can lose many times (trading it’s getting stopped out) and not be “killed” or out of the game (of life or of trading). In trading you loose all your money and are out but in life you can loose your life! This is scary but the reality is the probability of actual death is very small (depending on your risks of course).

    So a recap would be:

    1) Asses your risk tolerance (what can you risk?)

    2) Take mans small risks with the potential for big gains.

    3) Learn that like trading taking risk is just a part of life and it’s best to have a system to manage the risk than trying to avoid all risk.

    4) Have fun with this!

    All the best,


  78. Great article, but I wanted to add two more items:

    1) Don’t underestimate the role of luck

    Any success in your career will involve a certain amount of luck. You can either wait for it, or (like you said) seek out opportunities. The more opportunities you explore, the better the chances of getting lucky. If you have an ambitious career goal, its not going to happen because you put your head down and work hard in your current job for the next 20 years. You have to work hard, but you also need a lucky break, and the more favorable situations (startups, volunteer opportunities, etc) you expose yourself to, the more you improve the odds. And…

    2) Network, Network, Network

    Realize that people (whom you may or may not know) hold the key to making your dreams come true. Whatever your goal is, you can “deconstruct” into little pieces, and the smallest building blocks will be people. The more people you know, the more opportunities you can explore, and the more you expose yourself to good luck. The best part is that the more you network, the easier it becomes – it’s really the only “free lunch” in business.

    My Story:

    I will be leaving a steady and comfortable job in finance to pursue an MBA in France to seek out new experiences and personal and professional growth. Afterward, I would like to pursue management consulting for a few years to expose myself to a variety of different companies and opportunities.


  79. You Got Me A Raise

    And A Slap To The Face

    1. I read your article.

    2. Walk into my bosses office.

    3. Ask for a raise of twice the amount I expect in order for me to have some negotiating room.

    4. He approves the full amount, UNBELIEVABLE!

    5. And, he even backdates it 2 months to make up for lost time. Are you kidding me? What else should I ask for?

    I’ve been nervous about asking for this raise and I can’t deny that I was nervous in his office asking for the raise. I’ve been procrastinating until today due to nerves. What’s he going to do, judo-chop me?

    Why not just ask, it can’t hurt? The upside potential is much higher than the risk. Upside potential – I get a raise. Risk – nothing really, some nerves and maybe he says “no.” Well, he didn’t, he approved it, all of it. I’m going to go buy a Lottery ticket now; I’ll let you know how that goes, really nervous about the Lottery ticket though.

    To me it’s simple. You wrote “ask for a raise.” I did. And, I got it, so, I get your offer.

    I’ll tell you about the slap to the face on the phone/email.

    On a serious note, I can’t thank you enough for your post. You were a major influence in getting me off the schneid.

    Thanks for getting me off the schneid,


  80. Coincidentally, in 26 days I’ll be taking 7 weeks of unpaid leave from my well-paid-and-incredibly-stable-but-God-I-don’t-want-to-spend-the-next-18-years-counting-down-to-retirement government job. The risk in taking this time off is minimal – I just averaged my yearly income out to cover the gap and the job will be waiting for me when I get back.

    But oh, if I could find a project that I could use to fill those seven weeks that would be the start of something bigger, how cool would that be? The catch? I have two small children, and it seems like all the sites that talk about chucking it all and moving abroad, or taking low-paying jobs for experience are geared towards childless and often single people.

    If I don’t win, I’ll find something on my own (Develop my photography side-hustle more fully? Start writing a book?), but any new direction/inspiration would be welcome.

      1. Not to intrude on Emma and Shawna’s possible future business ventures, however, I would love to find out some more info as well Emma. I have 4 children and am very interested in any ideas you may have, however, I didn’t want to email you without permission.

      2. Julie, I don’t know if Emma has come back to read your comment, but you can easily find my email address if you go to my photography website

        If you get in touch I’ll try to keep you in the email loop.

  81. Gentlemen (Tim, Ben, & Reid) – thank you for the great posts and books. My life has benefitted greatly from the revolutionary ideas you have brought forth in the past. I hope this comment here opens up the opportunity for more positive growth in the future.

    The most recent change I’m making started about 40 days ago when I put forth a proposal to the five partners at my current employer. My current company is a healthy, well-regarded consulting company that serves several top 100 banks in the U.S., as well as many community banks and credit unions. The proposal was to move from my existing high-performing sales executive position to design and head up a brand new spinoff company that would serve multiple industries – including the banking industry – but with a brand new tech/software product.

    My goals in crafting and championing this proposal and subsequent company are simple: to build something from the ground up that I will have ownership in, to learn new things, to have new growth experiences, and to play toward my creative strengths. After two meetings, I received the green light.

    I’m now working with one of the partners to hire my sales replacement so I can transition to the new start up. The top candidate is getting an offer this week so the start up can move forward almost immediately. Name decisions, LLC formation, partnership contracts, formal business planning, etc. will then follow.

    I have introduced this significant volatility into my career because I know I need to continue to grow and learn new skills so I can evolve as an individual, coworker, friend, husband, and father. Disruption has also has served me well over my career and life paths, which have included the following self-directed risks in no particular order:

    • Championing my own career and accomplishments to move from Copy Editor to Copywriter to Creative Manager to Sales Executive in five short years.

    • While waiting tables after graduation, I picked the beans out of customer’s chili – at her request – and soon thereafter asked her for a date. We were engaged within four months and have now been married for almost 10 years.

    • Completing my last year of a multi-year banking school on my own – I paid a reduced tuition by proposing a T-shirt sponsorship, used 7 personal days off to attend, drove 10 hours to Dallas in my hybrid car to save money, and stayed in a fellow classmate’s hotel room for free – after my employer at the time felt it wouldn’t be a good use of my time or the company’s money. I have since landed a coveted industry speaking gig and a new client because of my involvement and graduation from that school.

    • Proposing a speaking topic on “Using LinkedIn to Increase Sales” to the banking industry’s premier retail conference with a note that, “if you want this session, I’m sure I could get someone from LinkedIn to speak with me.” They gave me the go ahead and four days to secure a speaker, which I did by leveraging my large LinkedIn network and Twitter to land Jenifer Grazel as a co-presenter.

    • Getting a Masters Degree in Creative Writing.

    • Reverse engineering the recipe for the Green Slime they used on the TV show “You Can’t Do That On Television” so I could sell lottery tickets for it to my fellow fourth-grade classmates….and narrowly avoiding suspension when Principal Johnson found out.

    In each of these scenarios above, it was a combination of saying both “yes” and “what if?” These are the cardinal rules for greatness! But, as you mention, each also comes with a healthy dose of risk.

    The current risks I’m facing – which had to be identified and mulled over before I put forth the proposal but have now become very real – range from “complete failure to launch” all the way to “overextending myself personally to the point it impacts my home life.” Oh yeah…and “everything in between except total financial ruin.”

    But I know myself and my history of adaption and evolution so am confident that I will be able to embrace the unknown with fast learning and creative execution. My current company’s resources and a supportive spouse are also big assets and have made the risks seem more like obstacles that can easily be bested. Of course, your mentoring would also help.

    So, I ask that you take a risk on me by saying yes because I’m certain it would payoff for all parties as I know I have lots to offer to those around me. And, to sweeten the pot, I’d throw in the recipe for the Green Slime… if you’re interested… and if Principal Johnson doesn’t mind. He’s kind of a hardass.

  82. I’ve just recently made the decision to drop out of college to become a freelance web designer. I dropped out because there was an inequity between the education I was receiving and my increasing loan balance. Besides that tuition costs were rising and yet more classes were moving online.

    Currently I’m part-time doing social media marketing. I’ve only once designed a website for a business client to completion ( I have a list of 25 businesses which have a website, but it’s ugly. I’ve offered a redesign free of charge to a local restaurant on that list and am in the process of completing it. I don’t know how much I could make from freelancing, but it’s work that I enjoy and the lifestyle I want.

    I suppose I’ve already taken the risky plunge, but I’m writing this more to vent and less to win a contest. Like Ben and Reid point out, most people are risk averse this day and age. Given the riskiness/perceived irrationality of my decision, I haven’t got much support from my family. Being a successful freelancer would validate my own beliefs and, I feel, would empower me to make the changes in my life and the lives of those I care about to move towards bigger and better things.

  83. Hi, I’m Negin Sairafi and I’m a creative entrepreneur. I think any career change requires a shift in perspective and attitude—so first and foremost I would like to change my attitude toward the concept of being successful; after all, sometimes success can be just as intimidating as the possibility of failure.

    In the next 30-60 days I would like to become the kind of person that isn’t afraid to take short-term risks for the long-term gain. Often times as entrepreneurs we find ourselves making decisions that will get us through the next week or month, rather than making decisions that will create great opportunity for success months or years down the line. Why?

    Fear. Fear seems to be the common denominator with all the missed opportunities. Resistance—that little voice in your head that says ‘this is stupid’ or ‘you don’t have what it takes.’ I want to take the leap of faith and create tactics to reach all the goals I have set for my company, no matter how big or small.

    The risks involved with going after my goals are financial hardship, failure to target the market effectively and being completely overwhelmed with the amount of work and lack of manpower. I’ve always been a risk taker—I turned down a great job right out of school to become a full time entrepreneur—but I can’t deny that there are moments of doubt, especially when I’m about to take big financial risks. I would absolutely love the opportunity to speak with you both. Thank you for your consideration.

    Negin Sairafi

    Owner – Creative Director

    Evoke & Imagine

  84. You guys have a lot of great responses. Good luck making a decision!

    I am stepping into a world incredibly vast and unknown to me right now (the web). I believe that I can motivate, inspire and encourage growth in millions of people around the globe. I believe there is greatness within us all. It is my desire to unlock mine and help as many others as possible unlock theirs.

    My plan is to start by creating a few very useful online businesses (underway) and work my way into consulting, writing and speaking. I believe that expression through art is as much apart of our DNA as anything else. Our creativity as a species is incredibly powerful.

    I am developing a passion for the search of this creative gene within myself and others. I have been living off of savings for the last 6 months looking for the path I want to commit to. I have found that path and will continue living off of what I can until I succeed in creating a brand for myself and my vision.

    I have worked as a pizza tosser, document filer, retail salesman, project manager, commercial real estate agent, kids club teacher, babysitter. I have built a school, a home and completed a landscaping project utilizing used tires, bottles and other recyclable materials in three countries. The eclectic list goes on, as I am sure it does for many “seekers”.

    From all of this work I realize my passion is to experience incredibly different cultures, incorporate what I have learned into my life and use it to inspire, motivate and encourage growth in everyone I come in contact with. I want to help people love themselves and view their world as a place of beauty, opportunity and fun.

    So, the question is not what changes I want to make in my career in the next 30-60 days, but it is how will I continue down this path of entrepreneurial spirit when walls are hit and obstacles seem high in the next 30-60 days? How will I continue to manage the development of a photographic portraiture website meant to help photographers follow their passion? How will I continue to develop an organization that brings tech-teaching and experimenting into the rooms of elementary classes? How will I continue to develop all of my ideas when I don’t know what the hell I am doing, or where my next step should be taken? (All asked with an enthusiastic laugh)

    I’m doing what I can with the knowledge and resources I have access too. And, I am thinking about the risk very opposite to the way my brain initially thinks about it. My brain says, “run” when there is ‘danger’, but I am telling my self to stay. To stick through the uncomfortableness of starting a business and see it to the end. I always thought “starting a business is a piece of cake, I’ll do it sometime”. What I didn’t know is that the first time around is difficult! But, without out great difficulty there are no great successes.

    There are folks who have gone through the great difficulty and found the great success; folks like you. Because of this I have been searching for a mentor to model and learn from in this digital arena as well as this thing we call life.

    I am 25, forever young, enthusiastic, motivated and have a clear passion. I would love your help.

    Be well,


  85. Julie, you’re more then welcome to email me. I have very few answers but a lot of questions, but I am sure our gaps are overlapping!

  86. In college I interned as a hospital chaplain at MD Anderson ( A BIG RISK!!!) but ended up gaining so much knowledge.

    When people were on their death bed thinking back on life, it’s not the safe decisions that bring peace. It’s risks that were successful or provided wisdom for future success.

    I’m recently married, young and have a good paying job. I’m taking the risk of starting up my own company by turning an award winning tangible reading system into a digital scalable version.

    Somehow I have gathered the strength to get seed capital, ask designers to lowering prices because of job’s potential to change the world, and build several digital relationships by cold emailing potential mentors.

    I plan on leaving my current job in September after launch. I used to dream of a teaching career. I am now having the time of my life staying up late building a company and taking a risk!

  87. Greetings, I’m Brian and I’m 29 years old. I’m currently working as a corporate charter fixed wing jet pilot. I’m in a salary position but I’m not receiving what my agreed contract has spelled out. I love flying and enjoy my job and the people I work with but I work a lot. It does not give me much free time to travel for pleasure. I do not want to work a job all my life. There is so much more to life like learning. Eventually I strive to be a contract pilot.

    What I really want is freedom of time. My long term goal is to travel the world learning different cultures (starting w central America) free of time and money constraints while managing an online business to sustain these interests. In my free time I enjoy working out and reading as many books on these subjects and learning as much as possible.

    One goal I have set in the near future is to create an online social network for people to give each other support based on what goals they’re working on accomplishing. On the users profiles there will be sections for them to post their current goals and wants as well as what they’re good at and their expertise. This will function as a way to search for people that are willing to help you get closer to what goals you have posted on your profile. There will also be a way to somehow give positive feedback to those who help you so as to vouch for that person and to show other people searching that persons’ true values. I picture this being public and free of charge.

    People helping people is good and will benefit not just the receiver but also the giver. I would love to get any feedback on this.

    I am currently looking into to help launch my idea.

    I have the drive and I’m willing to put in the work,

    Thank you

    Btw before reading this article I had already received The Startup of You. On the shelf ready to read. Ciao


  88. Thank you Reid, Ben, and Tim for such an amazing opportunity. So many of your ideas have resonated with me. First of all the concept that “Entrepreneurship is a life idea.” When I finished graduate school in speech-language pathology and began working in a hospital setting, which is very corporate in structure, I realized that it didn’t fit my entrepreneurial mindset. I have made many changes since then. which I believe have made me more resilient and paved the way for greater change. These changes have included changing specialties many times from adult traumatic brain injury (where I worked with many neuropsychologists similar to Rick whom you referenced), to adult neurogenics (stroke rehab), to pediatrics including autism. Most importantly, I have become an independent practitioner.

    My most recent change was a move to Chicago from Detroit to pursue greater opportunities in work and life. I find it ironic that my relatives flocked to Detroit when, as you quoted in the book, it was the “Silicon Valley” of its time. So sad to see the Grosse Pointe mansions with butler’s quarters reminiscent of Detroit’s heyday in sharp contrast to the sea of abandoned homes.

    So onto opportunities and risks: Fortunately I don’t see many red lights, mostly green. However for some of the areas that really excite me such as tech or entertainment I don’t have the necessary training.

    1)Transitioning into speech products instead of services. Developing a “muse.”-little to no risk

    2)Producing speech app to segway into tech-little risk

    3)Starting own rehab or developmental clinic-risk of time and energy

    4)Starting Youtube show for niche audience-friend in film industry has offered to help me produce show-Good example of “say Yes “-great time to be part of emerging market as tv audience switches to internet-Risk of embarrassment due to limited experience and possibly time to make money

    5)Develop “muse” in another industry using skill that translates such as organizational tool for Franklin Covey (trained head injured individuals how to initiate and organize due to injuries in frontal lobe)-little risk

    6)Get into disease prevention industry as I have seen the worst consequences of taking your health for granted

    7)Write, travel, participate in Operation Smile (similar to Doctors without Borders) for children in developing countries with Cleft lip and palate

    I think I better add the disclaimer at this point “Don’t worry I am going to own this decision”-had to steal that 🙂

    Other ideas:

    Move to Burbank, California to be closer to network in film industry

    Move to Silicon Valley because I have started to love all things tech

    By the way I am single and have no dependents except a West Highland Terrier. Although the biggest risk I perceive in moving is that I want to maintain my great relationship with my family/nieces.

    Also one of my best ideas was similar to that of the Timeline for Facebook. I thought of my idea (an online calendar/scrapbook to record your most important events) about a month before I started reading about Timeline coming to Facebook.

    I would be a great mentee. I could devote time around the clock to learning new skills and I would be greatly energized by a new industry. I would work for Facebook or Linked In for free or a nominal salary. Or pay to be a fly on the wall 😉

    Thank you for considering my post and offering this opportunity for mentorship/advice. I am dedicating my post to my dad, my favorite entrepreneur, who passed away too soon on the due date of this contest June 21 four years ago. I consider this contest a little gift from heaven 😉


    Karen Kozara MA, CCC-SLP

  89. Hi Tim, Reid and Ben

    Thanks for the great article and wow so many posts…

    What’s my story?

    I gave notice to a very well-paying job in marketing in the legal sector, in probably still the world’s most stable economy (Switzerland).

    In the next 30-60 days I am going to find an interesting job in Bangkok, Thailand (does not even have to be in marketing or communications). I don’t speak Thai, I have no previous experience in emerging markets other than travel, I have only a small network of people, but basically no friends in the region.

    I talked to several recruiters who all point me to Singapore and Hong Kong and advise me not to go to Bangkok.

    Somehow, deep down, I am convinced that I will go to Bangkok and find a fabulous job and create a new life whe I can learn new stuff everyday.

    What are the biggest risks? No job, no money, no opportunity, giving up all I have here for an adventure based on a gut feeling.

    Plan B? Come back to Europe and land a great job that will allow me to travel to Asia frequently.

    Plan Z? Even at 40, you can still crash on your parents couch if all goes down the drain! 😉 Besides, they totally support my move and encourage the risk-taking for happiness and a fresh start.

    So you see, I am in desperate need for some career and life coaching (something I might even be interested to turn into a career later on). 😉

    I would be totally and utterly excited to work with you guys on my Thailand project. Thank you for your consideration and I look forward to hearing from you!

    Cheers, Regi

  90. Reading Ben and Reid talk about overestimating threats, underestimating opportunities, and underestimating resources, I realized how succinctly these three concepts sum up my struggle with entrepreneurship. I know that my story is not very different from that of others, but in my case the hurdle of “underestimating resources” came first, then came “overestimating threats”, and finally came “underestimating opportunities”.

    My parents’ house, where I grew up, is in the middle of a busy downtown business district of a smaller town filled with small food and general merchandise retail outlets on both sides of streets. I was fascinated by the lively business environment in which wholesalers auctioned off their truck loads of merchandise to retailers, and retailers sold them to customers. No sooner was the dream of business ownership born than was put on hold as my parents explained the start up costs and their limited financial resources. Hence I was introduced to “underestimating resources”.

    This perceived inadequacy of start up funds that I learned early on has never left me. But it is now easy for me to see that it is a moving target: as I became more affluent so increased the size of the business I wanted to start to maintain the life style. In addition, with more possessions, there came the paralysing risk: what if I loose what I have? What if I am not able to keep up with Smiths? Hence I became familiar with “overestimating threats”. When these fears attacked, I invariably ran into the cover of safety, and then I could not even imagine the possibility of great rewards, or one can say that I started “underestimating opportunities”.

    In the current phase I believe that “underestimating opportunities” is a bigger hurdle for me than the others.

    In the beginning the opportunity to be an entrepreneur was a reward in itself and it was the primary motivation, and it was valued highly for there was nothing that I wanted more. However, this motivation was lost somehow and was replaced by money motivation, or striving for a better life style motive. It may seem counter intuitive that a billion dollar reward in future could have less motivational value than the possibility of achieving “be all you can be”. But the promise of a billion dollar in future was not driving me to action as it became clear that more or better possessions will not add to my happiness, or even if they did the effect will surely be marginal and short lived. I had to look for a bigger reward and I found it in “be all you can be”, and in learning to not fear the unfathomably great opportunities out there and have courage to follow my heart and avoid entrapment of short term gains.

    Reading “The 4-hour Work-week”, I was amazed at how well Tim echoed my predicament in the lines, “After years of repetitive work, you will often need to dig hard to find your passions, redefine your dreams, and revive hobbies that you let atrophy to near extinction.” That was an eye opener, and so was reading “Start Something That Matters” by Blake Mycoskie. Blake’s book brought back memories of how my parents had inspired me to make a difference in the world, in the sense that Gandhi and Lincoln did (just examples, it doesn’t mean that I am trying to be as great as them). I now believe that this “making a difference” is the biggest opportunity and the biggest reward and the most abiding motivational force.

    Before I go into my plan for changes that I am going to make in next 30 to 60 days, I believe a more detailed introduction of who I am is in order. I have been a software developer for over 20 years, and before that I received my bachelors and masters degrees in computer science. I found consulting to be more like running a business so most of the time I chose the format of independent contractor, instead of being tied to a employer as an employee. A few years ago I decided to start my own software business, but unpredictability of results and absence of cash flow and environmental pressures, and above all my own damn faults kept pushing me into making choices that brought me nothing more than meager short term monetary gains. However every failure comes with learning opportunities, and I came out wiser in two respects: (1) business is definitely for me, and (2) do not waste your energies in doing gigs for short term gains.

    In the next 30 days I commit to doing two things: (1.) Decide on what my first software product will be, and I will use my prior knowledge/experience and market need assessment to narrow down the list. (2.) I will learn mobile app development by reading books, doing tutorials, visiting blogs and other online resource. In the following 30 days I plan on creating the first alpha version of the product for one (most popular) platform.

    The biggest risk associated with this effort is the opportunity cost, that is, I will lose the money that I could be making doing consulting work. Additionally if there are delays the loss could be even bigger. I shall manage the risk by actively monitoring market demand for similar software products and will not hesitate to change direction if needed. In the second half of the project I will also try to get outside help in finishing the project faster and focus my attention more on marketing and preparing for sales.

  91. I quit my job as an analyst at a fund of funds 2 years ago to become a personal trainer. I immediately freaked out and moved in with my parents to try and figure out my life which led me to NLP, Tony Robbins, Tim Ferriss and PhotoReading. Three months later I moved back to New York, gave personal training another shot and started a health and fitness website/blog after reading Tim’s post on ‘The Truth About Abs’ and how to earn money through online marketing. I also became interested in the mobile app space after reading Tim’s post on Chad Mureta and app development. Two days ago I started working at a start up that develops mobile apps. My outcome in doing all this is to create an automated business which enables me to do what excites me, learn and add value to people, travel, help my family family financially and have more freedom in my life.

    My two favorite takeaways from The Start Up of You are on cultivating relationships and the quote by Bill Gates.

    “Building relationships is the thrilling if delicate quest to at once understand another person and allow that person to understand you.”

    “The most meaningful way to differentiate your company from your competition, the best way to put distance between you and the crowd, is to do an outstanding job with information. How you gather, manage, and use information will determine whether you win or lose.”

    I am 26 years old now. The dots have connected up to this point and I am excited for the road ahead. It would be great to speak with you both and get your feedback and advice. Thank you.

  92. As someone who plumped for a “stable” career as a Physical Education teacher I packed it all in to follow my dream to work as a soccer coach at a professional soccer club in the UK. I found myself in a cut throat world where connections matters the most and I had no networking skills, no strategies to survive, I was in essence a victim of choosing a stable job – teaching was never my intended career. In taking the risk I found myself out of a job after two years and unable to get a job back in Phys Ed as the funding in UK eductaion has changed.

    So early 30’s, married, new house that needs work I took a job in a primary school to pay the bills. I hate it. Something has to change, I need to change, I have to take control of my life, I want out of this current path.

    The sad thing is, like when you meet your favourite celebrity who turns out to be an idiot, I didn’t really enjoy working in the soccer industry. Awful hours, poor pay, no life / work balance – would I take that back? In a heartbeat.

    I must have my own way of doing things, in soccer? my own business? NLP? I need help with the risk, advice and guidance to help me with the first step, once I’m on track, I’m running

  93. Hello,

    I am a French student in an engineering school in the suburbs of Paris. I have the American nationality and I hope to, one day, come back to the U.S.

    I’m an entrepreneur and I’m working on my project part time.

    I understand that our main enemy here has two faces:

    – Our perception of the risk (too strong) which prevent us from taking risk

    – Our perception of the reward for that risk (too weak)

    I think an interesting idea is to focus on the fact that the problem comes from our “perception”, they are constructions of our brain and depend a lot of our environment.

    And interesting thing to do is to change our environment with low risks actions (or manageable risks) in a way that will motivate us to face bigger risks that we wouldn’t have faced without the input of our present situation.

    The goal is both:

    – to use our disproportionate “fear” of a risk to take bolder actions

    – to grasp the extend of the desired reward to enhance our perception of it.

    In my life, this principle could be used in that way:

    I could drop from my engineering school and go full time on my business >>> a “hungry” man with no choice will face bigger risk to get what he need. This approach lacks the enhancement of the perception of pleasure.

    I could enhance my life style, enter higher sphere of pleasure but in order to sustain this situation I will have to get more incomes. For example: Move to Paris, go in expensive private club used by successful entrepreneur. This approach induces both a fear to lose that situation and grasp of the pleasures of achieving my goals.

    By achieving the second situation I take a risk to change, but this risk is calculated and put me in a better growing situation.

    In that case maybe I would take risks on project that i fear doing like commercialize my organization system: I integrated the full GTD method in a totally portable system, it work on every computer with internet and is always synchronized with your android phone, less that 3 second are needed to see all the most important lists or add elements. But I’m not sure if it can be sold (legally).

    That was my vision of the risks I want to take in the next 30 to 60 days.

    William Baeyens

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

    I’m currently a marketing coordinator in a real estate office an hour away from my home. I want to stop the commute and transition to a higher paying role in sales or so I think.

    I had quit my job back in 2008 without knowing how bad the market was turning, so I started doing freelance marketing for companies and although the paychecks were every 45 to 90 days! I survived for 3 years. I also started a few online websites that generated money but died due to my lack of interest and knowledgeable ways to spend advertising money correctly.

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

    I feel that earning a paycheck every 2 weeks is nice! so I see the move as a loss of that comfort.

    I also think about the seasons out here in Chicago, if I worked in outside sales come winter I’m screwed because I have a crap car…no really it has a hole in the back window and it looks like crap.

    I see the benefit of working on my own time, no more 9-5 and I can use the money from sales to start a new online biz.

    I see the benefits of leaving yet I don’t do it because like you stated my brain is wired the wrong way when we talk about risk.

  95. Change I want to make: I’m currently an art teacher. I have 7 weeks of camp to teach and do not plan to continue teaching after the summer. I’ve been teaching for 5 years now. I’m planning on giving that up to be an entrepreneur. I have two mobile apps I’d like to build (to start with).

    Risk involved: If I continued in teaching, I’d probably have a steady income with a pension, but according to this posting, that is not guaranteed. It would be less risky to leave teaching and become an entrepreneur. My worst case scenario is that I will exhaust my savings. However, if that happens, I figure I can get a job again. If I attempt to start a company, the upside is unlimited. Exhausting my savings is a risk I am willing to take. It’s fun not knowing what is going to happen next, plus I really like ramen.

  96. – 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?

    Leave the current job that pays me 100k/year and focus on a career that will let me make a greater difference. At the same time let me be free to travel.

    5 months ago I had a baby girl with my fiancé. If I quit now, we will have to rely on my savings for I don’t know how long till i find the next job. I will lose all the benefits from this company.

    Four years ago, I picked up the book “The Alchemist”. After reading it, I left my job to travel around SE Asia for 16 months. After my travels, the old boss from the job I quit 16 months prior called and offer me my old job with a raise. I have been working for him since. I was terrified to quit my job the first time but I felt great when I finally turned in my resignation. This time around, I can’t bring myself to doing it again. I am now responsible for the well being of my baby girl and my fiancé. Risk is too high. What if I can’t find another job that pays me this well?

    It’s clear now after writing this comment that I need to quit this job but when I wake up tomorrow and see my little girl, I don’t think I’d have the courage to do it.

  97. I read 4HWW when it first came out. One of many books I was reading to learn as much as I could as I grew a new business, but it didn’t mean much to me at the time. I didn’t take it to heart, and it didn’t have an effect on me or my business.

    It’s a good thing there is truth in the fact that the master will appear when the student is ready. When I was pushed into reading it again this year, it profoundly changed my life, my family, my business, and my vision for the future. It opened my eyes to the fact that you can own a business and still be working it like a job.

    This year I watched a business I spent 5 years building crumble to nothing because of a vicious and crooked former business partner. I watched as my resources and energy were sucked dry by lawyers. My focus dragged from building a successful business, to fighting for what was right against an enemy I couldn’t beat. My options were to continue fighting an unwinnable battle, or take my lumps and move on. I could get a job in the same industry, get a job in another industry, or start something new and make it work enough to pay the bills.

    I didn’t realize it then, but I already had my muse business.

    This year I also watched someone close to me lose a high paying job he thought he would have forever, and he and his family had no way to cope. Psychologically, physically, and emotionally it was a traumatic and damaging experience.

    When I made the move to my muse business I had $23 in my pocket, hundreds of thousands in debt, no house, no vehicle, two kids, and a baby on the way. But I knew that no matter how difficult it was, it was the right thing to do, at the right time. And I had the right people around me to help it succeed.

    After what my family has been through, we’ve learned the skills and had the opportunity to grow from experience and now we’re able to say, OK, that happened, what’s next? What do we do tomorrow? How else can we make this work?

    We are able to look far ahead, and also manage the short term hurdles. The hardest part is keeping your head up in the trenches so that you can see the light at the horizon. You can’t see the light if you’re looking at the bottom of the hole.

    Having the ability to manage risk gives you the capability to gauge the situation, decide on a course of action, and determine the outcome.

    It also helps that my wife understands and applies the strategies that allow us to manage the risk in my business, in her business, and in our life together. We are living where we want to live, in a cabin in the mountains, where we can hike, swim or just enjoy the air sitting on our porch. We’re here for a year, and then moving to either New Zealand or Portugal. We are living how we want to live, Maria is launching her new childrens book, I started traditional Jiu-Jitsu, and I’m learning to kayak this summer. And we’re learning to be the best human beings we are capable of becoming. Consciously choosing the people we have around us, having the time to spend on ourselves, and the freedom to do what we want, not what we’re “supposed” to.

    I got to listen to an interview with Jack Canfield today where he said “it’s fear of rejection that will kill you.” Fear of risk will kill you too, you just won’t realize it’s happening until it’s too late. Learning to see the potential in every situation is what gives you the capacity to create opportunity. Embracing opportunity sets you free from “real” life, and give you the tools you need to live the life you want.

    I’m not out of the woods yet, but in the first six months of my new venture I’m making more per month than I did in the last five years, and in less than 25% of the time. In 18 months I’ll make enough to pay off all my debt. And I’m doing it living in an amazing place, with people around me that energize and engage me, spending more time with my wife and kids (4, 2, 10 weeks), and taking the time to learn more about myself and grow my awareness of the world.

    All this from asking the simple question; “How can I help someone else through their business challenges, so they don’t have to learn the way I did?”

    My muse business is a side project I’d been working on for more than eight years. I couldn’t find the right tools for my business, so I had to build them myself. Over the years we had a whole bunch of pieces that worked really well. They saved money and frustration for the work I was doing, but every time we needed something new it cost money to develop it.

    I thought, if these tools work for me there are probably others that need them too, so I put a small group together and asked “How can we take these tools, and put them together into something that will generate income?” We started building an idea that would give us revenue, and give other business owners the tools they needed to make their companies more efficient, more effective, and less frustrating.

    When my previous business disintegrated I was looking for opportunities. The best advice I got was to look at what I was already doing that I enjoyed, regardless of what it paid… I knew I could make a living doing this.

    What I had started thinking about almost ten years ago now had a life of its own. Everyone that I talked to got excited about it and wanted to get involved. We had something that was truly easy to use, our clients loved it, we knew it actually worked, and we were making money. Now I had to figure out how to get the message out.

    As we were building the marketing plan I had this “lightning” moment, where I knew that the sales process we were building would work for anyone. I wrote a one page outline about how you could introduce what we do to people who need what we offer, and started giving it to people I met in the coffee shop, at the grocery store, at the park when my kids were playing. Every page I handed out came back with an email or a phone call wanting to learn more.

    I tucked the page in the 4HWW, handed it to random people, and asked them to read it – after they read the book. Every single person came back and asked to work with us.

    As I went through the early stages of the business, grew the business model, and worked at developing our marketing strategy, I talked about the 4HWW principles with my team and my mentors. What I realized was that we’d built a strategy that anyone could use to introduce our tools to the world. Everyone working with us is on the path to fulfilling their 4HWW dreams.

    I believe every business should have the tools they need for life online, that are truly easy to use, at a reasonable cost. The more people that can help me show these tools to others, the more businesses I can help. I can provide a muse that anyone can start right now, and I want to pass it on to as many people as possible. And the more people that work with me, the faster I get to my 4HWW dream! My shift was from working my business, to showing others how my business can work for them.

    Being a resilient, intelligent risk taker allows me to excel and succeed in any situation. Being a resilient, intelligent risk taker, with consistent perseverance allows me to survive any situation and look forward to the next day, the next step, the next level. Being tested, and learning from my challenges, allows me to truly believe that I can do anything.

    In the next 30 days I want you to connect me with the 3 best people to help me show 1000 people a muse they can spend an hour a day on and quit their job. I know it’s not quite 4 hours a week. I’m working on it!

    In the next 60 days I want you to to connect me with the 3 best people to help me show 100,000 people a muse they can spend an hour a day on and quit their job. I’m willing to risk saying yes to whatever you suggest.

    When you choose me to mentor with you, I’ll donate 10% of revenue from your referrals to a charity or project you choose.

    Help me show people a muse they can start today, and get more people on the path to contentment, happiness, and the freedom of mind that changes the world.


  98. First, thank you to whomever has the never-ending privilege of reading all of these comments. There is some fantastic stuff here and I appreciate you taking the time to read about me.

    I’m writing you at a exciting point in my life: I’m about to take the ultimate risk – but it isn’t what you think. I’m not quitting my job to start my own company. Rather, I’m about to quit my own company to get a job for someone else. Crazy? Career suicide? I sure hope not.

    I’m 30 years old and started my own web company with a work colleague in 2008, with nothing but $10 for hosting, a $10 domain name, and a few shots of whiskey for courage. My friend and I built television fansites and soon had 200,000 visits per day. I made deals with the MPAA (wasn’t easy!), but founds myself constantly thwarted by Google changing their positions on various SEO practices. Things are still going well, but I feel myself isolated from the industry and working mostly in cafes with my laptop. I feel that to succeed – to really succeed BIG – I need to take the huge risk of leaving the company and going back to working for someone else. I need to learn more, meet some incredibly smart people. I’d love to move to one of the brain hubs of the online world. I feel that the internet is, more and more, becoming the domain of ‘big business’ and as a small business owner I think that I need to adapt the mind frame of “keep your friends close and your enemies closer.” I need to learn from the Googles, the Facebooks, the Linkedins.

    So, here I am. I’m wondering where I should work – who I should meet – and if it’s smart to give up what I have for the next big thing. It’s kind of “one step back for two steps forward” mentality, but I know that I can contribute more to the online business discussion. I’d like to be a part of that conversation and to listen and learn.

    Going to a full-time job for someone else is a huge risk for me, because I am giving up on what I’ve built. But that’s what I’m doing this month and I could sure use some advice!

    Thank you,


  99. Fun is important.

    Most people would suggest going to college, getting a job, or something similar. Almost no one would suggest quitting your job, giving away your stuff, throwing away your ID, taking a break from communication with everyone you know, and hitch-hiking around the US with nothing but a sleeping bag for two years. But that’s what hit me. I survived, I did not go crazy (too much), and I now have no idea what I want to do in the long run. The only difference being I like it now.

    It’s exciting as hell to be so off my rocker that nothing “normal” seems logical anymore. This is how the world is changed. Slightly sane people looking around and saying “you guys are fucking crazy!” and then creating a space in this world that is relatively more sane in comparison to surrounding stuff, just so they can relax somewhere.

    Thank god for the internet, it has allowed for these “weirdos” to find each other and work together, when in the past they probably would have just been hemlocked or burnt at the stake. I like this life very much.

    Life is to be loved. Happiness is our guide for improvement, not only for ourselves, but for the world. Amen.

  100. Hello World, Ben, and Reid,

    I am a young professional working on NASA’s next space program, which I’m sounds something like a dream job. It is a dream in some ways but after a few months at it I am finding that I do not want to do this for any longer than I need. I love to learn and speak about engineering/science but it seems that the task of being an engineer is not entirely for me.

    I have a degree (and a half!) in Aerospace Engineering, a minor in Psychology, and an intense passion for listening to and telling stories. My friends say that I have excellent intuition of people and ask good questions of anyone I meet. I think this combination of storytelling, intuition, and technical background really sets me apart from others.

    Every day I say that I want to start an entrepreneurial life and I decided yesterday that it is time to make the leap. I have the upcoming holiday week off from work so I will spend time getting more momentum on a product idea that my friend and I have been developing on evenings and weekends. If it goes well then I will give my two weeks notice and then make it work!

    It is quite risky to quit a job and hope for the success of a new product but I am ready. Over the last few years I have obtained a serious degree, practiced public speaking, and devoured books and blogs about entrepreneurship. I know some talented people as well and have worked hard to learn my own strengths and weakness. I think it is all coming together for my approaching adventure.

    I thoroughly enjoyed the audio version of The Startup of You and I have been a big fan of Ben’s blog for years. His blog is the only subscription I allow in my inbox! I also want to thank Ben for reaching out to me by email once about a year ago. It was a short note but very much appreciated. Thanks to Reid for also being a part of the book. And thanks to anyone that reads this! Cheers!