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.

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

  1. I load up Tim’s blog to send a design suggestion to a graphic artist … and I get first comment?

    (crosses fingers and toes)

    — Anthony

    PS – that recent Buffett post kicked ass Tim.

    1. Since 2 years ago i’ve graduated from university..and tilll know idon’t have any job to do…iam joblees..but iknow that’s my streght because i was not bound by some job.As ive is free.ican do anything what i want to do…basketball training..power lifting…write novels..and esspecially thingking about new career in bisnis.Because i don’t have any money i just thingking about start up bisnis with little needed of investment…like make organic is free and if talk about risk..there is no risk because i’m joblees..if you joblees make that to be your streght..because you can do anything what you resist…and having fun everyday with your own project

    2. Brillant article, I just discovered the 4HWW book two weeks ago and it has already changed my life. I’ve just started reading this blog and love the many ideas on it.

      I’ve taken some risk on and moved to Shanghai, China 5 years ago to begin my career as a golf professional. I’ve been teaching golf to the Chinese for the past 5 seasons and have built up a good clientele. I’ve learned the language and culture but now have a strong desire to take a bigger risk and bring it to the next level.

      I want to begin to diversify my career as only a “golf instructor” and become an author writing a golf instructional book targeted to the Mainland Chinese market. I want to then parallel the success of this book into developing my own golf company in China, establishing academies and performing golf clinics throughout the entire country. Finally I want to establish a golf link between China and my home country (US) promoting golf between the two countries with travel trips, summer camps, etc…

      In addition to my golf career I want to continue writing on my travel blog, establishing myself as a travel expert and one day work free lance publishing travel articles in my spare time.

    3. I’m a third year college student and I’ve come to accept the fact that I suck at doing anything that I don’t want to do, and I’m usually good at whatever I’m interested in.

      I can’t work a 9 to 5. I’m not capable of doing that well. I can work consistent 15 hour days in anything that interests me because it doesn’t feel like work, it feels like fun; and fun is not mentally draining.

      I’ve recently become obsessed with getting an developing android and iOS apps but really, I just want a source of money that doesn’t stop me from living my life. At some point in my life, I want to work as a hair stylist, programmer for google, bartender, venture capitalist, writer, marketer, news reporter… I basically want to try my hand at everything I’ve ever found interesting on a quest to find my passion.

      “Life only avails, not the having lived. Power ceases in the instant of repose; it resides in the moment of transition from a past to a new state, in the shooting of the gulf, in the darting to an aim.” -Ralph Waldo Emerson

  2. My risk, starting my own company! In the next few weeks I’m launching our first product along with Bawdy Zebra itself. I have four products lined up for release this year, the first one is finishing development at the moment (I should be doing that, not posting here!), the second two are going into development in July and the final one is in development for a Christmas release. Exciting times! This really is make it or break it (temporarily).

    How am I thinking about the risk? Well for me the risk is odd, Bawdy Zebra hasn’t taken much to create financially. Time and effort – but not too much cold hard cash. Unless something goes drastically wrong and my digital product kills someone, my financial risk is entirely manageable. More pertinent is my fear of what happens if I fail. I’m at the point where it’s very very easy for me to take risks with businesses and ventures; I’ve taken four major risks in as many years. However, this isn’t going to continue, the longer I remain taking risks without success, the more likely I am to end up in a position where I cannot take risks. In a strange sense, my fear is that if Bawdy Zebra fails, I will no longer be able to take risks because I’ll have to cave and do something boring and reliable. So yeah, not too scared of taking risks, I’m scared of not taking risks.

  3. Hi, I’m George. 25, Degree in Economics, living in Portland, OR, selling tea part time, promoting a chip company and chocolate company part time, and creating videos and practicing handstands in my free time

    -I will to do less of the work that is a means to an end and focus on the work that that gets me excited to wake up. My decision on what to do comes from asking the question “Is this activity in someway enhancing my abilities to create the future conditions that I desire?”

    -The risk involved in this move does not create an un-repairable worst case scenario, therefore it is a risk worth taking. Not working for works sake (sorry for sounding like a broken record..:) will allow me to give an idea the execution it deserves.

    Thanks for the inspiring article. -George

    1. I love this! “Is this activity in someway enhancing my abilities to create the future conditions that I desire?”

      Am I just trading time for dollars or am I getting some greater value out of my input of time. Great thing to think about.

  4. I dropped by the book store today to pick this book up. Learning is what people for get when they start working in there careers. Never stop being hungry for new workable knowledge. Fanatic post…..

  5. Risk is a constant. I’m not talking about risk always being around, I’m talking about how we all accept a constant amount of risk.

    If the risk is too high, we avoid the behaviour. If it’s too low, we find something more risky or increase the risk. This is of course a completly personal level of risk. A free solo rock climber accepts a certain amount of risk that others never would (myself included) – they do so to keep their risk at a constant level and keep climbing more and more difficult surfaces. But with more difficult climbs, their risk remains the same because their skill has increased.

    This risk is constant with investments, travel, learning, jobs and everything else in life. It’s our skills and abilities that vary on context, not the risk we’re willing to accept…

    1. @ M Donk: Yes, risk is both personal and situational. What may be risky to you or me — scaling a tough mountain — may not be risky to a professional rock climber. So nothing can be called “risky” in an absolute sense; it’s always relative to the person and situation involved.

      1. @Ben : Tonight daredevil Nik Wallenda will be crossing Niagara Falls on a tightrope, secured by a harness only at the insistence of event sponsors. Any way you look at it, the endeavor is risky, be you an amateur or a professional. Think about it – if it weren’t risky to the pro, why would he even dare it?

        Sure, in the broad philosophical sense, there may be no absolutes (or as Tim likes to say, “reality is negotiable”), but this does not legitimatize circular reasoning to say that risk is always relative. Risk is a reality and should be evaluated realistically using reason and evidence.

  6. I want to change my focus from looking at high level things (business model, deployment strategy, etc) and focus on coding front end. This is for my own trip that I’m founding with two friends. One of our biggest goals for this startup is to be able to retire out parents within the next 2 years.

    The risks going through my mind is: I’m suppose to be CEO, have an eye on everything but right now it doesn’t feel fulfilling enough. I feel like I should be on the battle ground. On the grounds building our product together. Im more of a fuzzy than I am a techy. Coding scared the shit out of me before but it’s gotten better. I’m not afraid anymore. Im just sucking… For now. I’m afraid by focusing on the nitty gritty, I’ll lose my ability to be creative and create awesome ideas:).

  7. Thanks for the post gent’s. I felt a bit sceptical about high risk-short term = low risk-long term, but it does make sense. Comparing it to a country would suggest China is going to have a big explosion at some point in the future too, a Tiananmen Square on a larger scale maybe.

    I’ve got an ever growing long term to-do list, and one that’s been sat there a while is getting a new website started (I have 3 ideas, 2 already have URLs) but I’ve not made a move as it’s risky.

    The risk is I am also studying for my degree which I’ve fallen behind on and it’s currently got my priority as well as needing to upkeep my travel blog which although I’ve raised from 850k Alexa rank to 170k in a couple of weeks, is also getting a bit rejected and not generating as much income as it used too, hence the need to diversify.


  8. I am currently working as an accounting clerk for a medium-sized startup while finishing my bachelor’s degree remotely. This month has been a big month of change for me as I am looking into a project management position in the agile programming world. While this would be a fairly major career change, I think it will give me valuable experience to be familiar with both the accounting and programming disciplines, and I am excited for the challenge.

    I would be thrilled to get advice from the two of you and also from anyone in the programming world.

  9. This article hit home. It’s been two years living on contract to contract basis, or on a quarterly basis, not just with one client, but several. The used techniques I learned in my Vipassana meditation course to overcome the anxiety I experienced nearing my roll-off dates, especially when I decided to buy a home without financial foresight. I had faith in the thought that if I remained strong in my present state, it’ll pave the path in to my future state, which would be as prosperous, or more than my current state. This was the mantra I repeated to myself.

    I validated my faith by journaling my feelings. Whenever I felt anxiety, my meetings would conflict, creativity would seize. The future didn’t look promising. But in a matter of hours (talk about being bi-polar), I cleared my mind by going on spirited motorcycle rides and immediatly after, doing something artful. I would produce good creative, either for the client, or for myself. When that occurred, the anxiety would fade, and I my promises would be delivered to my clients and the clients would offer more projects, a handful at a time, actually

    The best way I could describe my behaviour, is as “fluid”. Rarely I would say no, or rarely I would say yes, I would simply agree, and say perhaps. I would go back to white board an design UI, a workflow, and deliver the iteration. This allowed me to have multiple contracts, and be in two places at once (from a virtual office).

    I am writing this message from my new home, 4mths into my mortgage and I feel good about the future! I get consulting offers at least once a week via Linkedin.

  10. I have seen too many honest businesses and people suffering because of the crisis. I want to start an exchange traded fund (as opposed to a hedge fund, which is only accessible to the rich) that protects people from global downturns like the current one. Ideally this would be available to the Australasian market as we are very vulnerable to what happens in major markets like the US, EU and China.

  11. My risk was just taken. Having two apps developed for iPhone after seeing an opportunity. Will be getting out of the military in less than a year, and stretched myself to the limit knowing it puts me in a vulnerable position financially.

    How am I thinking of the risk?

    It doesn’t matter that much if I lost 10k or 10mil because I can recover from it, and just have to make sure I improve myself from it.

    P.S. The first one will be on the App Store in about 3 weeks.

  12. Without too much “fluff” the biggest change I am seeking to make in my career currently is growth. I have been in my current role for a little over a year now, and really feel that I have gotten all that I can out of it. Everyday I do the same thing, and there is no real challenges that I face on a day to day basis, this frustrates me.

    I’m actually pretty unsure what my next move is going to be though. I have been taking online courses for SQL because the foundation of my companies software is SQL, and I was hoping to get an opportunity with our data team with this knowledge as well as some freelance opportunities outside of my company. But, as soon as the course I completed was over a job became available that seemed to fit perfect with what I have been working on. However, they deemed that I was not qualified for that role because I did not have an IT degree.

    In addition to this a past job that I applied for as recently been opened. The only thing with this job is that it is completely unrelated to what I have been working on, and is in sales. I’m not sure how this move from one end of the spectrum to the other will be viewed within my company, or if anyone has even noticed. Another side note a recent former colleague of mine took a job in Charleston, SC roughly two months ago. He loves and has been asking me to apply to a position down there but I have yet to pull the trigger. The biggest issue I have is that I have a lot of student loan debt and I’m not sure I can afford the cost of relocating, but I think my biggest issue on this one is just that I am being a wus.

    Thanks for reading this I hope to hear back from ya’ll would love to get some more specific insight on the stuff that I am doing, but finding it hard to fit in this one comment box.

  13. Hi all! My name’s Brad and I’m from Perth, Western Australia. I’ve been playing around with technology my whole life, right from when I was 5 coding my first game on the Atari ST until now at 30 I find myself in an advertising agency running the digital strategy team. I have no formal qualifications and am entirely self-taught and am earning unbelievable money based on that.

    The thing is though, I’ve never taken a serious risk in my career. I love technology, but I’m in a tiny market. I know I should branch out and move out of this City but I’m comfortable.

    I have the skills and the curiosity and passion required to be successful in this field and in business but I just can’t seem to take the leap. I have a negativity bias.

    My goal is to start an App development company. I have 2 apps launched (Perth Zoo App and CSBP Insights) both for clients and loved the experience. Check them out if you have the time.

    I have a list of about 60 app and start up ideas and I just need a little push to get started. Thanks for your time!


    1. Brad – I am in the same boat as you, I am in a market in the U.S. with the goal of putting together a creative team for App Development and Starups. I’m not sure how or where to get started.

    2. @Brad – Cool to hear you’re thinking about how you can take more risk and perhaps turn your side project of app development into a full-time thing. You might think about how whether there are app developers / entrepreneurs in your professional network — and, if not, how you can develop more relationships with people who are taking the risk you’re thinking about. Your network can give you the nudge you need, as well as guide you on specific next steps.

      1. @BenCasnocha I’ve reached out to Brad as we are in the same city and potentially the same boat. 1+1 = greater than 2.

        p.s. very much looking forward to reading the book. I wholeheartedly agree that now more than ever an entrepreneurial approach needs to be applied to career development.


    3. Hi Brad, my name is Gavin Williams, I’m the Career Advisor at the Emirates Western Force rugby team here in Perth. I’d love to chat over coffee. I think we could be on the same wavelength given I’m into tech and about to launch my first app.

      Can you please get in touch with me via LinkedIn.

      I’d love to help you with your career development.

  14. Presently I am a 20 year old part-time sales associate at Best Buy whom made the decision to forgo college and any aspirations of landing a “steady job”. I always felt that my goals would not be reached nor my ambitions satisfied any sooner with the attainment of such things.

    In the simplest terms: I always wanted more then what conventional wisdom offered and I didn’t want to wait until I was old, grey, decrepit and in a wheel chair to get it. I heard all of the objections from friends and family ad nauseam yet still have kept calm and carried on – never losing sight of my end game.

    My intention with Best Buy upon employment about 5 months ago were simple: infiltrate the organization from the inside, figure out whom all the key decision makers are (ie: those whom can write a check for the value I offer) and transition from a regular, hourly sales associate to a contracted consultant, speaker and trainer with the company. You know: travel around from store to store across the United States, help improve company performance and employee moral all the while making a name for myself and earning a commensurate return considering the one I provide. A real “quid pro quo”.

    They would be my first credible, large client and from there I would be able to transition to other large companies doing speaking and consulting. I love helping folks and this was my plan. That, write books and ultimately: establish credibility in the marketplace.

    However, the road has been filled with quite a lot of obstacles – many of which I did not anticipate would be there considering my point of origin (coming from the inside then up versus the outside in). To sum it up plainly: despite my emails, phone calls, outstanding sales performance and insistence I am getting no where.

    The plan now? To either find a way to do the former with Best Buy or leave the organization and pursue such work elsewhere. Keep in mind: I have no fancy initials after my name but I do know I have tremendous value to offer.

    Ben. Reid.

    Lend me a hand.

  15. There is a definite “call to YOUR action at the end” 🙂


    In the last few years, I realize many many things. For the past 6-7 years, I’ve been wanting to start web projects and startups and always fell in the same traps: procrastination, never-ending organization & planning, doing ALL myself because I thought it would be easy and waiting for everything to be perfect before launching. What happened? Well, I never launched anything and had to continue build websites for small & medium interprise in my city to make some money, which I again did everything alone: cold calls, finding contacts & references, selling, marketing, my own websites, business card design + print, programming, wireframing, graphic design and CSS & HTML coding.

    Although I consider myself good in certain of those things, I hate it. Then while reading Tim Ferriss 4HWW, 100+ Mixergy interviews of successful entrepreneurs and many books on self-improvement, it finally slowly and slowly ‘clicked’ in my head:

    1- I need to surround myself with great, positive minded entrepreneurs with tons of drive. Right now, although my friends are great, I feel that whatever I say nobody understand… They’re just not entrepreneur and I seem to be trying to nudge them to think like such but they’re not: I’m wasting my time and annoying them!

    2- hire people and delegate MUCH more before I drive myself insane (80 hrs/week) with low revenues

    3- and very recently: focus on my strenghs. God, that one took me time to understand and grasp. I was always trying to know everything in every domain thinking I would, somehow, someday know a lot and cool down and take it easy. It does not, the more things you learn, the more average you are at everything and less focus you have for what you rock.

    Now that’s the key point I got: my biggest, biggest strengh is that I have an -endless- flow of ideas. Great ideas. Ideas that works (tested and proven on my clients websites). And when they don’t work, well I analyse, check, double-test, and go on until I get it to work. I have so much ideas in fact that it gives me trouble sleeping, because I wake up every 15 minutes to write down a new idea for whatever customer or project I’m working on. What’s amazing is that it’s actually effortless for me: ideas just pop out of nowhere.

    So I thought: “What is it that’d be REALLY awsome, that I would wake up and be amazingly happy to do and that I’d actually be good at doing, working on a real strengh and (here’s the important part:) ONLY work on that strengh?”

    The answer: Website consulting for innovative companies, web 2.0 websites, high-traffic blogs like Tim’s 4HWW and Mixergy, etc.

    Here’s my risk part:

    So 2 weeks ago, after listening to the 100 Andrew Warner free podcast from itunes (, I subscribed to get the 600 others and noticed something: his website has SO much potential it’s freakinly amazing. I believe Andrew is simply the best interviewer I’ve ever seen, because he doesn’t get carried away by the guess success, he ask the right questions, etc. He’s amazing and his interviews quality are -outstanding- BUT his website is really bad.

    It’s beautiful, but this is a content website… with courses (premium $$) and if I’m a blogger or popular website owner, I can’t find the content I want at all… So I don’t stay… or pay. And mostly it lacks a clear AIDA design: Attraction, Interest, Desire, Action that could be easily achieved. No access to the content = don’t know it’s there = no sales.

    So anyway, I prepare a long email with pictures with arrows and examples and a list of amazing ideas and send it directly to him with no expectations (at least a ‘thanks, I’ll take a look’). But nothing. In the meanwhile, I continue working on other projects and keep having new ideas for his website so I send a second email the next week with the new ideas. Still no anwser. I send the same email to his employees hoping for the best, and no answer either. Then I set to find his personnal phone number which I find and I call him 3 times, each time getting the message saying he doesn’t anwser his phone…

    So anyway, in the meanwhile, he finally reply one of my email saying he doesn’t have the time to read too many email, just send it to my employees…


    So here’s my call to action:


    I believe my ideas for his site are amazing. If they’re not, I’ll work until they are. And I’d like to do my first consultation & management of the easy, incremental changes I want to propose him to improve conversion, access to content and raise in a major way his sales.

    Although I can program everything myself I have no interest in doing so (not my strenght), what I want is get the best ideas, TEST them, then improve them. I believe I can DOUBLE his sales with those changes (in part because there is SO much opportunity on his site)

    >>>>> BUT I NEED YOUR HELP: Does anyone KNOWS Andrew enough to HELP ME get in CONTACT WITH HIM to work FREE for a month on improving his site in the most incremental and safest way for his customers as possible. I will work FREE until I DOUBLE his sales, it’s that simple.

    If someone is ready to help me, I have prepare a case study to convince Andrew with screenshots, comparaisons, split testing cases, etc that I could send to you to ask for your opinion, and forward to Andrew.

    What’s in there for me? Well, if I get to work with him and really improve his sales, then:

    1- that could make an AMAZING 1rst CASE STUDY for my new consulting business.

    2- He’s interviewed 700 high profile guests and it would be amazing to help them after, adding value to their site.

    3- It would allow me to FINALLY surround myself with amazing, talented, positive, entrepreneurs

    4- It would allow me to travel

    5- I would LOVE it

    6- I’m a thinker, this is what I want to do


    Thanks a lot to all


  16. Ben and Reid,

    Do you guys read Nassim Taleb. This mirrors his philosopy, and it’s very readable and practical. I’ve shared it in many places; I’ve never seen one article so clearly state what I’ve been trying to do since leaving law school.

    I’ll get to my 30-60 day change, but first some background – the near term change is a culmination of the past year and a half.

    I left law in December 2010 without a plan – seemed less risky than continuing with a career I didn’t want. All I knew is that I was good at teaching people the LSAT, and that I could probably make some money off that.

    Every step of the way, I took the sorts of risks you’re talking about. For instance, I said “yes” to writing some LSAT explanations, even though there was no short term benefit. The downside was low. When the early numbers justified it, I kept on writing for six months, with very little short term income. I could see the long run value.

    No one understood at the time, but now that I make a decent income in royalties, people understand.

    I’ve used this income to forego work in the short term and invest in new skills. I’ve been learning computer programming since January.

    In the next several weeks, I’m going to launch a webapp to help people learn LSAT logic. I’ll be able to find early users because I am the new moderator of – a subreddit I restarted two weeks ago, and am continuing to grow.

    There are no certain gains to starting an LSAT subreddit, or making an LSAT webapp. But there are no downsides, either, and the upside potential is huge.

    As an anonymous internet commentator put it, I am investing my time, rather than spending it. The start was difficult, but things have been getting easier with each passing month as the seeds I planted grow ready to harvest.

    In short, I aggressively managed my downside risk, and exposed myself to as many events with large upsides as I could. Enough of them have paid off.

    Like Reid, my worst case scenario keeps getting better as well. If my app doesn’t provide me with a full income, I can now take a programming job, and get paid to improve my knowledge. I already have one lined up for September.

    Thank you for writing this excellent article,


    TLDR: In the next several weeks I will forego income to launch an LSAT webapp. Might amount to nothing, but there’s no risk beyond that. Could turn into something great.

      1. @Graeme – Great story, and love your distinction between “investing” your time and “spending” your time.

        @Jon – We cite Taleb in the book itself (where there’s a more in-depth discussion of these ideas). Taleb, among others, has commented on these themes, but we were more influenced by Ramo’s discussion of resilience, which is why he’s cited/linked to in this particular blog post.

  17. Hello, my name is Robert, a young biologist working for the Japanese government. I’ve been here for two years, and the first year was very difficult. I love my job now–I am organizing an international DNA design contest this summer–but my government contract expires immediately afterwards. The prospects in Academia look pretty bleak right now, though I would be happy living either in America or Asia. So I am thinking about either (a) start a company here in Japan designing ornamental transgenic plants (b) freelance writing grants (c) searching for big industry jobs in America as I have no idea how to go about that here or (d) sell all my stuff and live on an island and learn to surf, then crash with friends in San Francisco next winter until I find something. So many possibilities make it difficult to recognize the real oppurtunities, thanks!

  18. Some smart dude once told me to ask myself “what’s the worst that can happen?” and if you can live with that consequence, do the thing you want to do!

    I’ve been back in school and working at a job that pays very little but is flexible enough to let me follow my dreams! It’s totally worth it!

  19. Hello! My name is Kristina. I’ve never posted a comment on Tim’s blog, although I do read most of his posts, except for the body posts (not much into that). But, after reading this article and Tim’s last post featuring Derek Sivers (and his blog) I have decided to post a comment. You see, I am trying to say YES, where I would normally say no. When this post ended with a call to post something, I said NO, I am not going to post. But, I reminded myself that I am saying YES now. This is a risk for me, and I plan to YES, where I would normally say NO for the next few months and see where that leads me.

    As far as the career move goes, I have no idea of what risk I could take. I have a small shop on etsy where I sell vintage, upcycled home decor and bohemian style decorative pillows. I’ve been working on some new designs of my own to create and sell. Maybe I could try that? I do fear that no one will buy my designs or they might come off as amateur or not well made. My worst case scenario is that I make these items and they won’t sell. The worst thing that could happen is that I lose money on the supplies and my labor to try these ideas out. My best case scenario is that people like them and they sell. I believe I should take this risk, I have nothing to lose in doing so, only embarrassment and time wasted if I fail.


    1. Kristina,

      Saying “yes” is a great default for generating more opportunities in life! Check out our post on Eric Schmidt’s recent commencement speech on why saying yes is starting point of most good things:

      1. Hi Ben,

        Great article. I’m replying to your post because I have posted three times, well within the 5 PST limit, but it seems to get erased. Other than a tad long, I don’t think is bannable. Here it is:

        Thought provoking article. 

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


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


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

        In essence, what The Startup of You suggests is that while taking a risk with one’s career will not eliminate risk itself (after all, it’s systemic), it might just be the best insurance from irrelevance, because deep down, we want our existence and our life product to matter. 

        The most fundamental question you can ask about anyone or anything under the Sun (be it an action, event, product, business, non-profit, person, idea or risk) is: does it (s/he) matter? The Startup of You helps so that you may answer that question for your own life with a resounding YES.


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


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

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

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


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

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


        What I am giving up?


        The two main risks we take seem to be either forced (surviving) or deliberate (thriving). One grows out of scarcity thinking and the necessity to meet our immediate needs – e.g. old company downsized so now one searches for a new job, even in a different industry. This type of risk is no risk at all because the alternative (the jobless status quo) sucks. 

        Thriving, deliberate risk is true risk, not born of necessity and as you note, innitially appearing as a worse alternative to the comfort of the current status quo. I’d like to think the risk I’m taking is a deliberate one. 

        I just graduated from law school and have a good law job lined up. In short, by taking the above proposed “risky” path, I risk forgoing and likely “will” forgo financial safety, prestige, giving up the savings I have accumulated, leaving behind the certainty and comfort of the environment and people I have known, or just looking foolish in general. 

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

        While, by living the comfort of law, I will risk a lot of external, safety oriented things, what I will not risk is what drew me to law in the first place, the ability to analyze problems and manage the risk in each. When I think of lawyers, I think of risk management machines, looking at the downside, costs and flaws, always analyzing them more than any potential benefits. Just as the sole function of a speed governor in a car is not to let you go past that speed of no return, it is the job of a lawyer to manage and calculate risk for a living. 

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

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

        * Sales

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


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


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

        * Advertising and Marketing

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

        * Law

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

        * Human Resources

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

        * Learning

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


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



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

  20. I’m going to be honest, I haven’t heard of the book you guys co-authored. I’ll probably be picking up a copy tomorrow morning..

    So, let’s see…

    These next two weeks I decided to take unpaid vacation, rented out my apartment on airbnb to cover the rent, and I find myself here re-evaluating the past four years of my life (I graduated college in 2008).

    The comment on ‘negativity bias’ is exactly right: I have been avoiding risks, with potentially long-term positive pay-offs, at the precise moment in my life where I should have the least worry to take (what I perceive to be) huge risks.

    1) I have been (re)-learning Python these past few months, and I just signed up for AngelHack NY. I have a few crazy ideas in mind, I know I can’t execute them on my own at this point, but maybe I can convince a few others who can? This isn’t really a risk I’m taking, but more of a step towards ‘doing’ rather than ‘talking about doing.’

    2) Last week I spoke with Shereef Bishay at devBootcamp. This post just pushed the likelihood of spending 10 weeks in SF during the Fall class. This feels like a big risk (changing cities and leaving the comfort of a steady paycheck), but is it really? I think I can say now that the bigger risk is spending the next twenty years unsatisfied. Right now all I risk is the short-term benefit of a paycheck.

    And what’s the payoff? It could be huge, not just from the things I will learn, but also the people I will meet and the experience in itself.


    1. @Alan – Great contribution, and I love your point that the payoff would include “not just from the things I will learn, but also the people I will meet….” Agreed that expanding your network is important upside.

      And enrolling in something like Dev Bootcamp, to me, represents the perfect kind of risk to take given your circumstances: it has the opportunity to rocket your career forward by helping you develop valuable skills and networks in a short period of time, all while having capped downside risk.

  21. I don’t think I need to reiterate what others will say about how this is a fantastic post, but I will: Thanks Ben and Reid! You guys definitely hit the nail on the head with this one in terms of risks.

    What you said has basically been my risk mindset for quite some time now, thanks to reading books and blogs from people like you two guys and Tim, and also Seth Godin, as he talks about the “lizard brain” all the time.

    Anyway, I am writing this comment from Seoul, South Korea. I took a risk 2 years ago coming here to teach English right out of college. I got lots of criticism from friends and family for coming here that it was risky, especially with tensions between the North and South and the language barrier.

    But I really didn’t see it as a big risk at all. Sure, it was uncomfortable to fly halfway across the world (I am originally from a suburb of Philadelphia) into a different culture with a completely different language and to be away from friends and family. But I knew this would be a tremendous learning opportunity and experience I would never forget. Besides, when I thought about the possibility of moving here, I was excited. Once I felt excited and slightly uncomfortable, I knew I had to do it. The downside was that I was out of my native environment and that I had a girlfriend in the States that I had to leave behind. The upside was that this was a great opportunity on many levels, and it was even higher paying than my job that I had to get immediately out of college while I filled out all of the paperwork and processing to get here to Seoul.

    This comment is dragging on, so long story short, 2 years later, I am here in Korea, I am learning the language, I got introduced to Jiu Jitsu, I’ve gotten to travel to 8 countries, and have been able to travel home a few times. I also have a new (Korean) girlfriend who is beautiful and treats me well. And I have time to work on new business ideas and think about new risks—I am launching my blog next week. My life has changed completely because I decided to pack on up and move to Seoul for a few years.

    Sometimes I wonder what I would be doing right now if I didn’t make that choice and “played it safe”…

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

    Lol. Make some money would be nice, otherwise applying for a job as a chemist again 🙁 I recorded some videos teaching people how to make their own cosmetics. I’ve been struggling to figure out the right formula to launch it. In the mean time I wrote a booklet about wedding planning and so far by exploring options for my little book, I’ve come up with a number of ways to market my classes and I’ve written another booklet about business planning mostly to document what I’ve learned in the past two years, but hopefully people will find it helpful enough to pay for it 🙂

    (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 don’t think there’s much risk involved. A few years ago I took a huge risk proving to myself that I could do things on my own. Now, how quickly I can turn a profit will determine whether or not I have to start looking for a full time job again. Part time I’m a holistic therapist which gets me by, though I have moved to cheaper accommodations and as much as I don’t want to, if things don’t turn around I’ll have to sell my car 🙁


  23. Hi guys,

    My name is Bennett Russell. I am finishing up my bachelor degree right now. I have a few classes left and then the next step of my life is somewhat in limbo. I have always desired to go an entrepreneurial route, but I have had some issues figuring out what levels of risk I should adopt in life to be able to make that a reality. I have an amazing wife who supports me in whatever career path I ultimately want to pursue, even if that is a ‘riskier’ path in general.

    I have real goals that I want to put into play. I read your entire book while at the bookstore and the idea of keeping my life in permanent beta is what I know I need to do to make my career goals a reality. I saw what you guys are looking at doing with one reader here and I want that opportunity to be able to hear from you and ask you some questions. It sounds like a truly once in a lifetime opportunity. When I read an opportunity like this, it reminds me of the Eminem song from from the movie ‘8 mile.’ Having one shot or one opportunity. Sometimes you only get one shot or one opportunity to make that initial push in a particular direction. If I don’t get picked, I will forge my own, but the opportunity would still be absolutely spectacular and could be one of the more influential moments of my life.

    Please consider me as a choice.

    Warmest regards,

    Bennett Russell

  24. Hey Reid, Tim and Ben,

    I’m a 22-yr old iBBA grad from the top business school in Canada (depending on which magazine/newspaper is reporting the rankings that year.. seriously.. soo flawed) and I just quit my job to pursue my dream of becoming an entrepreneur. When i say “just”, I literally mean JUST quit my job- it happened on June 13th, 2012 at 10:00AM EST.

    So I think i might be disqualified because I already took the biggest risk of my life (it’s a weird feeling of relief and extreme fear) but the timing of everything, right down to reading this blog post, freakishly all came together.

    I officially graduated from undergrad June 14th, 2011 (exactly one year ago) and unlike my other friends, I did not have a job lined up at an investment bank, accounting firm or CPG. For some reason, none of the information sessions or talk about salary/promotions at those companies info sessions particularly tickled any form of excitement in my body- not even in my pinky. Jobless and a complete disappointment to my 1st-generation parents, my sister and I picked up and went over to Thailand and Korea. Not so secretly the best decision of my life—got laser eye surgery while in Korea (better technology + half the price), tried all sorts of food, saw firsthand how behind North America is with technology.

    Fast forward 2 months later, and we were back in Canada…the second the plan landed I received a call from a budding fashion label that was under the Umbrella of one of the top CPG’s (Joe Fresh) for an interview. At the same time, my friend’s father who is the CEO of a medium sized company asked if I would come and work for him full-time. His industry does not attract business school s students and is not sexy AT ALL.

    Seriously, so so not sexy…I went from jobless to two job offers: fashion label vs. trucking/transportation/storage Company.

    Risk #2: I took the job with the Medium-Sized company working directly for the CEO because I had my heart set on becoming an entrepreneur; what better way than to learn from an entrepreneur and one of the most well-connected individuals in Toronto?

    “So so so not sexy” So not sexy to the point that my first battle was tactfully telling all of senior management ALL of their mktg materials were awful and using ‘moving’ language made no sense at all the everyday person. Taking on that position I was forced to innovate and create within smaller budgets; reach far far far out in my network to see if anyone out there could fulfill design specs, build websites (which we also eventually learned how to do), seek partnership opportunities/build relationships… that position literally forced me to become a “jack” or “Jill of all trades”.

    Along the way, I was asked to build a private health clinic from scratch and create all the marketing materials, web content, design, interior design etc… it was all a great learning experience. There were huge ups and downs, but let me walk you through the past 3 months…

    I started feeling restless and started wondering if I had made a mistake about not going to a CPG. Hearing my classmates talk about their jobs and all the fancy business jargon being used so fluidly in conversation made them sound so professional and accomplished. I couldn’t discuss what I had done during my days, picking out paint swatches for the interior of a clinic, guessing/taking a risk on a possible initiative without knowing if it’d be successful etc… I began to feel like I had fallen behind and started to seriously question everything. Everyone around me was saying successful entrepreneurs get their foundation + skill from working at a large company first. Did that mean I wasn’t going to become a successful entrepreneur?

    I had the great blessing of having a fellow school-mate and someone who had successfully started a few of his own businesses work alongside me at this medium sized company. I would talk about my concerns openly and one day he told me to read up on Tim Ferris. Hence, I began following you on twitter two days ago, and this blog post showed up on your twitter feed, TODAY. The Day after I quit my job which was the day I took Risk #3–the biggest risk of my life.

    My friend re-assured me that CPG wasn’t the end-all/be-all of successful people. At this point at work, I had fallen into a bit of a very comfortable routine. Soon after, another friend who had recently quit her job to join a start-up told me this over coffee: “you’re not square enough to be doing a square job.”

    That’s when it hit me: i had legitimately let my ‘risk’ analysis talk me out of pursuing entrepreneurship and to create excuses.

    At that coffee meeting, she also suggested I travel with her to Hong Kong in July. It was a quick comment in passing, but she followed up. and followed up. and texted. and facebooked.

    I took a step back, looked at my life, goals, career-desires; I could not get there by being where i was. At 22 years old, I could go to a CPG and get that ‘training’ but I’d have to stay there for a few years to climb high enough to gain real experience. Realistically, being an ABM, I’d be doing repetitive work day in and day out on a spread sheet…

    that idea immediately was axed.

    That left one thing: do my own thing or join a start-up.

    I still don’t know 100 % what it is I will be doing, but I quit my job to travel and force myself to take on this decision. I quit so I could learn more and become excited about life again.

    At 22 years old, I don’t have a mortgage, spouse, children or anyone depending on me; so NOW is the time to travel and see the world. I’m hoping this helps with creativity, direction and overall career fulfillment.

    I am a 22-year old new grad that has quit an excellent corporate job after a year to take a stab at something new. I don’t know if I made the right decision and I have no idea where I will be traveling to after HK; no idea where to go, how to get there, where to stay, what to do, but i’m taking a chance.

    My end goal is to make an impact on this world, and I’m hoping having taken this risk, a big leap in the right direction’s been made and that the risk analysis I made was correct.

    Everything discussed in this blog was so reassuring; Most of my life i read about all the cool stuff people were doing with their lives, but this is the first time I’m actually taking a shot at it…

    To sum up my risk analysis:

    – realized to go to a CPG/Multinational, i would have to stay years and years to gain ‘management’ material experience;

    – instead of Why Now? it’s Why Not now? 22 yrs old without anything holding me back… why not take a risk now? If i lose everything, that’s not so bad because I don’t have much to lose

    – doing this will force me to grow as a person and analyze my strengths/weaknesses and I hope to try something/anything to generate income on my own that’s not a salary…

    Everyone’s question after I say “I quit my job” is… “Do you have something lined up?” …my answer: No. But I’m ok with that for now… I just hope to meet and have the opportunity to talk to really successful people (not by measure of just money, but fulfilled with their life, happiness etc..) and different people.

    Apparently I use to be a good writer, so I started a blog last week with a few brain farts hoping to stir up controversy.. jking… its my way of trying to document my way of becoming ‘unsquare’ again…

    take a look 🙂

  25. I have lived by these rules for most of my life, taking opportunities to do things that excite me over ones that are risk-averse.

    While in high school, I went on two international exchange programs, to Japan for 6 months at age 15 and to the USA for the final year of my schooling. I then studied film at university, with my career choice beginning a series of major life changes, most of which occurred in the week of my graduation. Taking the gut feeling of relief that I got after missing out on a house contract, I made the decision not to tie myself down to a ‘normal,’ stable life of mortgage payments, and in the same week, graduated from uni, quit my job and took on a volunteer role as a camera assistant on my first feature film.

    Since then, I’ve worked solely in the film industry, riding the financial ups and downs while still saving for amazing travel experiences including extended trips to India and Sweden, both of which contributed to my personal and professional growth.

    For the past twelve months, I have been building a company alongside my freelance work, with the goal of creating projects based on audience demand, and building business models around their popularity. We are focusing on using social media, crowdfunding and viral views to draw attention to projects and plan to capitalise on that demand through paid high quality downloads, DVD and Blu-Ray sales and merchandise. It is a system that is well on its way in the US, but is incredibly risky here in the Australian industry, where filmmakers tend to rely on government grants rather than creating their own income. I want to break from this model and treat filmmaking as a business instead of an artform.

    At 28, having worked in the camera department for my career to date, producing is a new pathway for me, but I am hungry to learn and have spent a lot of unpaid time developing my skills and studying in these new areas. Our current project, Wastelander Panda, is proving that the ideas work, with our Prologue clocking over 100,000 views in its first 5 days online, and our audience building everyday. We are constantly using online statistics and audience feedback to develop the model for the next stage of the project, and plan to do this for all of our projects in future.

    I am keen to continue expanding both my skills and business knowledge, especially by developing my international networks and creating relationships with people who think in terms of business strategy. My goal is to treat each of our film projects as ‘start-ups’ and apply similar business models, from raising capital and creating products for niche markets that can then expand globally.

    As well as proving worthwhile for my current business, your post has made me realise that these new skills are an investment in my own future, and will enable me to adapt and change to new jobs and opportunities in the future. I look forward to reading ‘The Start-Up of You’ to transform my new-found business thinking to myself as a person.

    Thank you!

    Kirsty Stark


  26. Hey guys,

    Thank you so much for your thoughtful and motivational post.

    My name is Paul Dennis, and I currently work in an OK Corporate job with OK pay, and I’ve decided that life is too short for it to be OK. I want to live an amazing life, and I am committed to making that happen somehow.

    I want to quit my corporate job in the next 60 days and become a full-time Android and iOS app creator. I wrote the code for my first app and it’s been on the market for over 2 years now, and I just hired a freelancer to work on my second app. I’m so excited, but yet scared as hell on the other hand, since I used all my money I made on my first app to pay for this second app to be built in a shorter amount of time than I could have done it. I’ve always loved improving things, and thinking of ways to make life easier and more enjoyable for people, and I really feel like I could make a huge impact on the world through creative mobile apps that help people’s lives become just a little bit nicer, and hopefull a LOT nicer.

    I can’t express in words how thankful and grateful I would be to have two people like you give me advice and help me out, I’d have to make sure I wasn’t dreaming if it actually happened. I want to thank you from the bottom of my heart for your time and generosity for helping whoever is selected in this contest, you’re sure to make a big difference in someone’s life.

    Take care!


  27. Hi, Ben. Hi, Reid. Congrats on the great guest-post. I really enjoyed it!

    My name is John-Paul, but my friends call me JP. I want to completely change my career in the next 60 days. Specifically, I want to work for myself.

    Your post inspired me to respond because it identifies exactly what’s kept me from trying my hand in this new career – fear of risks and failure. I am 30yo, married, and the father of a bright and handsome, 3-month-old son. Since his birth on Saint Patrick’s Day, I have felt this burning need to abandon my current career path, and invest in a future more fulfilling, fitting and resilient. My current career has me working in the health insurance industry, providing client management and feeling unfulfilled, unrewarded, and seemingly defeated. I’m really good at what I do, and I am confident my drive and tenacity will always help me find success in anything I try. Unfortunately, I greatly fear that if I try the wrong thing, I will fail to successfully provide (even at the most basic level) for my wife and young baby boy. The risk of failing them and not having the cushion to recover is petrifying… so much so, it continues to keep me from taking a step, let alonge “the plunge”.

    If you feel inclined, please help me to find direction.



  28. The British SAS have a great motto that really summarizes this post – Who Dares Wins.

    I’m thinking of quitting my job at a profitable startup to work fulltime on a non-profit I’ve founded on the side and which I am more passionate about.

    I’m analyzing the risks from every standard angle:

    1. financial,

    2. what it will do to my social life,

    3. psychological since its a great unknown and what impact will that have on my health/stress levels

    However, the one area of risk most people don’t think about that I spend most of my time focused on is Karma Risk (i.e. the risk of not focusing on a “For Good” endever full time) . I feel like if I build this company that is focused on alleviating one of the large issues in this world I will have done my good deed on Earth. It will be something I will be proud to point to on my death bed. The question ultimately that I would like help on is does Karma risk outweigh the more mundane risk?

  29. My name is Kendall and I’ve actually already made 1/2 the career change, but have yet to make the second half. I’ve recently left my tenure-track university faculty position in order to temporarily help out with a family health emergency. But I need to make the transition to something that is relatively location independent and for which I can ideally use my writing, technology, and teaching skills.

    The late Ray Bradbury said something like, “You’ve got to jump off cliffs all the time and build your wings on the way down.” Well, against all advice, I’ve jumped off the cliff, and could use some help building those wings. I’ve worked up a rough plan and have started developing several ideas to make things work in my new environment, including interning at a literary agency in New York, but having the chance for feedback and course corrections would be greatly appreciated.

  30. Wow,

    Did this post come at the right time or what? There is obviously no such thing as coincidence.

    I am one of those “freelancers” and as I am sure most of us who don’t have the steady paycheck – I am occasionally thinking if getting a “real job” would be a good option.

    Well, it wouldn’t. And I know that just like the last (and the only) time I did “the 9-5 thing”- despite a good salary and a respected position – I was MISERABLE!

    So we basically pay for having the freedom of our own schedule and control of our lives with the uncertainty and no guaranteed income. I will take that any day over being miserable, thank you very much, corporate world.

    So here is what I want to change in the next 60 days:

    I have been running my own fitness consulting business for almost two years now and most of my income comes from working with clients one-on-one providing training and nutrition consulting services.

    But my greatest passion in life is teaching and being a speaker, conducting seminars on health and fitness is my dream and my ideal life. I would do that for free any day. By teaching seminars, I would be able to reach and improve the health and lives of many more people than is possible individually one-on-one.

    I do some life coaching and enjoy it very much, but speaking in front of a large group of people energizes and excites me. I have done it once so far and it is surely what I was born to do. I loved it!

    My audience loved it too!

    So I want to make the transition from what I am doing now to teaching seminars full-time. That would be a complete career change. I would gladly do it for free in the beginning to gain some more experience and because I love it so much.

    I spend hours every day reading, listening to audio books and seminars so I have a lot to share with the world. I just need a platform that will allow me to share it. (This is why I am starting a new blog that will also offer my book on it).

    The risks are obvious: no income in the beginning and it is also going to be difficult to get into the field. Both of these I can handle since having ups and downs in my income is something I am used to and – “difficult” is what I eat for breakfast.

    While I am sure there will be many other people with worthy goals, here is why I think you should grant me this mentoring opportunity:

    1. I am 28 years old, HUNGRY for success and highly coachable

    2. As an endurance athlete, persistence is my middle name (literally, since in my home country (Bosnia) we don’t have middle names 🙂

    3. You would significantly contribute to my goal of becoming financially independent before I turn 30- and the universe would pay you back multifold

    4. I guarantee you that it is next-to-impossible to find a better mentee than me (I will do an extra, extra step to achieve what we plan and not stop until it is completed)

    Thank you!

    Amir Pozderac

  31. I read this post earlier in the day but I was 2 hours too late. Womp womp. I still want to give my 2 cents anyways. I’m 22 with half a business degree. for the past 5.5 months I was in Nigeria having an international living experience (amazing). Before that I left my hometown to move to a bigger city for work experience and broadening my horizons. I did all this because I wanted to see what else was out there and learn and grow. Of course, my family is pressuring me to finish school and most of my friends graduated this year but I don’t really let that phase me.

    I’m back in my home city and now I am looking for a job that starts with equal or higher pay than what I was making when I was living in a bigger city. It’s a challenge because this requires me to apply for jobs that on paper might say I’m not qualified for but I know I am capable of doing these jobs so I just keep applying. I’ve had some good interviews and I’m confident that I will get what I’m looking for because it’s not just about the money, it’s about having a job that stimulates growth and is challenging. I have to work harder to sell myself in the interviews and beef up my resume a bit but I really have nothing to lose. Most people won’t even bother applying for jobs they don’t think they’re qualified for but I just don’t buy a lot of the recruiting BS that’s out there these days.

  32. Fantastic post.

    Bennett, I love the term ‘permanent beta’. That provides a very valuable perspective and a quick and dirty way to describe our motivations for living the way we do.

    This post could not have come at a better time. I recently graduated with my Bachelor’s degree in business administration, and I’m deciding which direction to go. I’m very open to taking calculated risks, especially in working ‘learning jobs’ vs. steady / high paying jobs. In fact, my goal has been to move to a foreign country and work ‘learning’ jobs for a few years. I think that this point in my life is the best time to learn as much as I can about myself and to develop as a person.

    In the last year, I’ve really come to realize the incredible value in experience vs. formal classroom education. Saying, “Yes” was one of the best habits I’ve ever developed. I would love to spread inspiration and motivation to people who need a shift in perspective and a little push to get them going. Helping people realize their potential is the best form of service I believe I can offer, and I have seen success with those around me, so far. This is my catch-22, as I am finding it difficult to add legitimacy to my cause when I am so young and many people struggle to listen to someone who is not a published author, professional speaker, etc.

    The Internet and social media has really changed the way we live our lives, and I’m looking for a way to use this shift to help people help themselves. I believe that living and working with a purpose vs. for monetary gain is the best path to success.

    If given the opportunity, I would use the time and e-mail interaction to target the up-and-coming opportunities in the tech world that could help me create a community of like-minded people who want to help others. I would also love to build great relationships with the suggested contacts, and to learn from them in the coming years (and offer them something in return).

    Congrats to whoever is chosen! Seize this opportunity and be the person you envision!

    Best Regards,


    1. Allan, glad to hear you like the idea of “permanent beta.” It’s a term from Silicon Valley that we think ought to be a life/career idea for all of us — we must always be improving, iterating, fixing bugs, growing. We go more in-depth on what permanent beta means in chapter 1 of The Start-Up of You.

  33. hi guys,

    hope I’m not too late to share some of the stuff I have tried for the past year and the challenges I am pushing on to overcome.

    What I had tried:

    Recently help built a new joint venture startup but didn’t turn out well in the co-vision we are inspiring to built in the long run and really felt the pain knowing that the business had failed to realize and to move on.

    Now working on freelance work just to fund my own on-going tests of ideas:

    + In the midst of building a ecommerce marketplace for small & medium business (to realize my earlier vision which doesn’t came through as shared above)

    Other areas of testing done concurrently and earlier (without much capital spent less my time & commitment)

    + a meme site (tested no of ways to drive new traffic – started to see a little growth after a year)

    + a competitive spying site for landing pages (just started – testing out the ways to drive new traffic and testing of product ideas to drive return visitors)

    + a automotive site (failed but still trying – even though its ranking well in search engines – lack of repeat engaged visitors)

    + a q&a community site (failed – lack of on-going community engagement and members)

    + a technology site (co-founded) – failed – lack of commitment which is essential for a team effort to succeed.

    Challenge Facing now:

    Facing a dilemma now of should I still carry on pushing on as a single co-founder (tried getting earlier co-founders to join in but got burned) especially with my mortgage coming very soon in about a year+ period. Given the fact that I know how much more my run rate is going to be as a solo bootstrapper and not to mention the super lows during this period.

  34. Thank you Tim, Ben, and Reid for this,

    I think this type of thinking is a plague to so many people. Using our foresight to create so many worse case scenarios that we can’t focus on amazing opportunities that are truly attainable. I’m the only one in our design and photography firm that works solely in a marketing and sales capacity. The rest provide a creative skill along with constantly building awareness about what we do. When sales are soft, and the higher revenue clients are fewer and far between, I feel more responsible. I’m more comfortable reaching out to gate keepers at more comfortable times, that are not even the decision makers, and lower revenue companies that “seem” like they would be easier to close than a major client. Am I crazy? Our team produces amazing work and I need to be the BIG MOUTH letting the BIG BOYS know that we are here, ready, and capable of producing the visuals that they need. Why do we take being told “no” so personally? That and the terrible fear that we are going to interrupt something important at the exact time that we are reaching out to the individual. Madness. I’m determined in the next 60 days to banish this cowardly fear and become more confident in connecting with individuals that have the ability to help propel our firm onto the radar of huge clients where it belongs. I know Tim is right when he said that the competition is most fierce for “realistic” goals. 95% of people not believing that they can accomplish greatness. My biggest fear needs to be not becoming one of them.

  35. 2 1/2 years ago I left my steady, secure job and regular paycheck to go out on my own and use my passion for business and marketing to start a digital marketing consultancy helping small business owners increase clients, sales, search ranking. Although it’s been a challenge (to say the least), I wouldn’t change it for the world.

    Every day I ask myself, what can I do differently to help more clients, and how can I get out of my comfort zone today?

    No matter what you do in life, there will always be an element of risk. The question to ask yourself is how much risk can you handle, and what will it take to for you to succeed?

  36. Is this open to people outside of the US? If so I’ll share with you my comment about the change I’d like to make. Thanks for the great article, Tim, Ben and Reid.

  37. The first step is the hardest part, getting over that fear, that rustling noise in the bushes that your own mind makes or hears from others who fear. Once you get to love the rustling noise, it gets a whole lot easier.

    Its highly unlikely that you are about to be eaten by an imaginary furry monster. That imaginary monster may just turn out to be a fantastic dinner for the tribe.

  38. After settling in to the family life, it became more and more difficult to nurture my entreprenuer wings. I have had plenty of ups and downs but still feel far from prepared. I love music so much and have spent years of time and effort engaged in it and wish I could figure out a way to make it my career.

    I decided to get a graduate degree in accounting to give me some stability and hopefully get me the push I need to create a solid foundation that my family and I can financially build on. I’ve worked my ass off in construction through the recession and look forward to entering a new arena in the business world.

    I hope one day I can somehow merge music and accounting, two themes distinctly different and apart (I did actually write some comedic accounting rock songs for a professor that got me some extra credit). I also have some creative ideas for marketing commercials to promote my CPA firm.

    My goal is to be indispensable at wherever I work or to start the best damn accounting firm out there. Wish me luck and look for me either on MTV or building my firm.

  39. My name is Max and I just finished my Bachelors Degree in Liberal Arts & Sciences in the Netherlands. Looking back, and forward, some of my choices could be called risky.

    Doing a Liberal Arts & Sciences degree in the Netherlands is regarded by most people in my country as very strange; “so what will you be working as?” is a question I always get when I try to explain my study. Nonetheless, getting out of my comfort zone in Amsterdam and going to an international college has been put me through a growth I couldn’t have imagined ever.

    Now I am done with my undergraduate studies. Everyone is doing a graduate study. But I am not an academic; so not for me. Next year I’m interning at Sjaak Hullekes (, a young and upcoming Dutch designer I have met during one of my unstable income jobs (modeling). The company is small, there is not a lot of money, but I feel that in such a small idea I can be right on the ball and learn tons.

    However, right now I am typing this up in New York, where me and some fellow students are for my final Geography course; a field trip. And this city is so damn inspiring. One of my traits, being that I have at least one new venture idea a day, is on steroids here. Executing any of it seems like the only logical step. How, where and what seems like a matter of little time to be answered. All I know now is that the more I’ll take on stuff that I fear, or at least are not completely comfortable with, the more I’ll be ready for anything that comes up to my path.

    This mentorship and this contact with you guys will bring me in touch with people that are doing something I am not doing and in a place where non of the people around me are. Something new and something that will make me grow.

  40. What’s something that you believe in that almost no one else believes is true?

    My answer used to be: start ups are less risky than corporations. You invest in three things when you join a startup: the chance to learn at an exponential rate, an elite special ops caliber group of co workers (who are all driving to the same goal, be successful or die) and groundbreaking technology. The flip side? Being a name in an org chart.

    I did it once (starting in 2009) with and now we are fortunate enough to utilize the reach and firepower of a corporation to save lives.

    I was employee 50. My goal is to enter a company earlier and earlier.

    Let’s do it guys.

  41. Hi – I’m Clarissa. I’d first like to thank you for the valuable insight provided in this post and the opportunity to receive mentorship. I have to be honest and say that I almost didn’t leave a response, because I thought about how many people would respond and the likelihood that my entry would be chosen would be slim to none. But then I thought about it and realized that’s the type of thinking we’re trying to combat here. It really does apply to even the smallest situations in life.

    On to my answer.

    I’ll actually be making a very big change in my career in the next 30-60 days. I’ll be leaving the “stability” of my full time job (and the comfort of the south and the southern hospitality) and moving clear across the country (Cali) to return to school full time and pursue a Masters degree for my passion in producing (theatre management).

    What are a few of the perceived risks associated with this move? (I’ll keep it short and just list off a few.) The cost of living is WAY more expensive in California than in the south (Georgia to be specific). Graduate school is extremely expensive, and it’s even more expensive because I’m attending a private school. My research is proving that scholarship opportunities are few and far between for graduate school, so I haven’t fully worked out how to pay for this program I’ve committed to for 3 years. I’ve already been warned that I will not have the time to hold a full time job because the program is intense. I’m taking my current car, that I’ve had since high school, but I can’t guarantee it will be along for the entire ride. Are you starting to see the picture here? Let me also throw in that I have no family, no connections, and a few ideas for side hustles to possibly help bring me income. I’m literally going to start from scratch.

    Even with all of those things stated, I’m completely sure that my biggest risk would be NOT going. I’ve lived my life long enough in the “safety zone” to know that I’m not really living at all, and that the “good stuff” will start soon.

    So how am I thinking about all of this? I plan and prepare for as much as I can (my current profession is as a planner), and I’m leaving the rest in the hands of the Universe, knowing that I will be caught should I fall. I’ve also concluded that IF somehow things just did not work out – I could go home and sleep on my parents couch until I figured out another plan…or found another job. I have a very good feeling that that won’t be necessary.

    Thanks again for this opportunity.

    1. @Clarissa – It’s great to hear you’re thinking about your Plan Z (as we call it): “I’ve also concluded that IF somehow things just did not work out – I could go home and sleep on my parents couch until I figured out another plan…or found another job.”

      Thinking through Plan Z very concretely is helping you take the risk you know you ought to take — way to go!

  42. Hello my names is Dominic and I am currently going through a career change. I left the army after 7 years and have gone back to university to help me achieve my goals in life.

    It would be a great honor if I was picked and I believe your help would greatly accelerate my career change and success.

    Thank you for your time

    Kind regards


  43. Ben & Reid,

    I really appreciate the insight that you guys provided in this piece. I’m currently at a crossroads in my career (at the age of 27). I furiously pursued my MBA following an undergraduate degree in marketing, and have spent the past 2 years establishing myself in the financial services industry. I’ve experienced success to this point, and am beginning to take a larger role in our firm’s management team. The business is primarily commission based, so I know how the freelance writer must feel (and am marginally confident that I won’t “starve” if I develop the courage necessary to take a risk like this article outlines).

    I would absolutely LOVE the opportunity to be mentored by the two of you, and reading this article seems serendipitous with it’s timing. I was in a meeting this morning with one of our senior financial advisers, and realized then and there that I had no desire for my career path to mirror that of his. I need a change, and more than anything need the courage, or push, to make that change. I love learning new things, and pride myself in my ability to embrace the absurd and think outside of the box. These are not exactly the things that my office values, and leads me to believe that the right FIT exists elsewhere (either that or I need to create it).

    If given the opportunity to learn from you, I will not let you down.

    Thank you for your consideration.

  44. Hi I’m jadon, I’m a honours year industrial design student,

    I have been offered a safe and well paying job in New Zealand but I am

    passionate about working in developing countries focussing on

    Social corporate responsibility but have no idea where to start.

    It would be nice to have the cash but money can’t buy the dream.

    Looking forward to hopefully having both.

  45. Amazing post Tim.

    My Background. I’m originally from Bolivia, I am a rising senior at Duke University, and I started ShelfRelief while in college (Google my name and you’ll see some entrepreneurial articles).

    In the next 60 days I am convincing my parents to let me take a year off of college to start an offshored Sales team in Bolivia for ShareFile (recently acquired by Citrix). The project has been approved by the CEO, Jes Lipson (who’s also a Dukie and I met last November). We are starting on August 1st and running until December, then reevaluating (either growing the team here, expanding to Costa Rica or shutting down)

    I see no risk, if everything fails I go back to college and get my degree, if it works I can make $50,000 by december and make over $30,000/month starting February 2013. My parents are afraid I will never go back to college, and they see it as a long term risk.

    I would love to have the chance to talk to Reid and Ben. I admire Reid a lot, I even remember taking some ideas from the letter he wrote to his early adopters at LinkedIn thanking them for joining early, and drafting a similar letter to my users at ShelfRelief. I’d love to hear Ben and Reid’s thought on what to say to my dad to allow me to take this opportunity.


    Tito Bohrt

  46. Hey guys,

    Great post – Just what I needed. I first read Tim’s 4HWW about 2 years ago. I completely abandoned my uber-stable playboy lifestyle as a golf pro / bartender in a ritzy ski town and moved to Seattle to pick up a hard core sales job and see if I could hack it working from home.

    18 months later I’m crushing the sales position, but that’s not the best part. I’ve also picked up 2 freelance writing jobs doing copywriting for golf companies in my spare time which have effectively doubled my monthly income. It’s a huge risk doing the writing deal because if my boss at the sales job finds out I’m finished, but it’s totally worth it.

    My next step is to leverage the freedom my freelance writing jobs provide and take this show on the road for a long term globe-trotting expedition. I’ve never been more scared of anything in my entire life, but I know in my heart it’s the only way.



  47. As a future pastor, it has been really exciting to see how well ideas about entrepreneurship translate to full-time vocational Christian ministry.

    Regardless of one’s personal beliefs, it is hard to argue that being a pastor is a strenuous line of work. Most I know work 6-day weeks and are generally on call 24-7. Even causal outings with friends can turn into impromtu theological discusisons and “real quick” counseling sessions.

    And there are certainly no fewer “risky” opportunities. The pastorate is HIGHLY driven by networking and relationships. A degree may or may not get you into the door of a church, but a recommendation from a well-respected pastor certainly will. Risky situation #1 above is particularly relevant.

    I am looking forward to using truth from anywhere in advancing my career, working toward being a highly skilled, well connecting, loving shepherd.

  48. I have a very comfortable BD role at a tech company in Silicon Valley; I’ve been there for the last four years. I’m originally from Asia, graduated from an Ivy League college with degrees in business and engineering, and am currently in the US on an H1-B visa.

    The change I plan to make is to leave the safety of the nest with my technical co-founder and launch my start-up. Within two years, I hope to raise my series A and thus qualify for an EB-5 visa that puts me on a path toward a green card.

    There are several risks that I’m considering:

    1. I’m giving up a comfortable job and lifestyle

    2. My startup may fail

    3. I may not raise enough money to qualify for an EB-5 visa

    These risks are mitigated by the following factors:

    1. I have enough savings to last me for several years, with some adjustment to my standard of living

    2. I will learn a lot more by actually launching my own effort than by continuing in my current role; this experience will be useful if I need to find a more “stable” career in the future

    3. My startup idea is based on my field of experience but also incorporates a field that I’m passionate about; I believe that passion is half the battle for success

    4. I believe that same-sex marriage will be legal within five years, thus qualifying me for a “fiancée visa”; this reduces the risk of my never being able to work in the US

  49. Hey guys… My name’s Dan, I’m 26 years old, and I live in Austin, TX. I’m a software engineer at a very large corporation and just transferred departments about 4 months ago where I felt more opportunities would be available.

    A couple of days ago they announced a new position would be created to help an under staffed area of our department. I’ve only worked for my company for two years, and would be considered by most to be under qualified for this management type position (although no exact job specifications have been created yet). I do know that a number of the projected duties are already being handled by me though. So in the next 30-60 days, I plan on writing up a strategy on what I’d like to bring to the table, and then sitting down with my potential new manager and making my proposal.

    The biggest risk I see is the fact that I’m so new to this department, and this could come across as cocky or arrogant. I don’t want it to seem like I’m unsatisfied with my current position, but at the same time this has the opportunity to launch my career into a whole new level, and drastically increase my role in the organization.

    When I break it down in my head, there’s not much I would be losing by just going for it, but the nerves still exist. Luckily this article being posted just two days after this opportunity popped up, does give me confidence, and makes me feel like this is an even more “meant to be” opportunity. Thank you guys for the great advice!

    – Dan

  50. Last month, I switched industries and my functional area by taking a new job in a geographical area that’s 4x more expensive than my previous location.

    Have I left a lot of life’s little comforts behind? Yes. Was it risky? Yes. Do I regret my decision? No, not for a second. It’s the best career decision I’ve ever made.

    I had stopped learning new things in my previous job. At my new job, everyday is like drinking from a fire hose. I’ve rejuvenated my career by moving outside my comfort zone.

    Don’t let yourself get so comfortable in your career that you’re not willing to try new things or do something different when things go stale. When things go sour, take it as a cue to find the next mountain to climb.

    Good luck!

  51. At the ‘risk’ of what Japanese call ?????? (an “unwelcome service” – ask Tim how to read it), I think this concept of intelligent risk could be greatly be improved, and more widely marketed, if the concept itself were given a taste of it’s own medicine.

    For example, What are the risks, positive and negative, of not just your generously personalized offer for the most thoughtful comment, but also one’s acceptance of the challenge?

    I’m willing to risk it.

    I’m two weeks away from starting an International MBA in the US. I want to study management consulting and entrepreneurship in emerging economies, but I am struggling to decide which geographical region in which to spend the next couple years. I have consulted with friends, family, and professionals, and I have narrowed the choice down to China and the Middle East.

    My risk assessment? After spending the last four years in Japan, I am familiar with China, both in language and culture, and will likely learn quickly; the Middle East, however, I know almost nothing about and am sure to struggle (that’s okay). But in terms of business opportunities, China is an eclectic bandwagon, the Middle East, a desert caravan. To use your scenario, going to China is traversing the river for some venison, while going to the Middle East is peeking with instinctive hunger into the rustling brush behind me.

    Your advice would be of great value. While pale in comparison to the unacceleratable experience of Mr. Hoffman, I am sure that I, like Tim Ferriss and Ben Casnocha, am a lifelong learner with no less passionate curiosity and drive.

  52. I really think you should give Kendall a call. I think it would be a pivotal moment for him.

    This article really resonated with me when you started talking about knowing how to roll with the punches. I spent the last few years freelancing and not knowing when my next paycheck would come in. I’d go for a month or longer before landing another website, but the payoff was always better than any 9-5.

    I got tired of the feast and famine cycle, so I’ve been going from company to company, putting out fires and moving to the next. I’m much more willing to take risks because I know that I can support myself in the lean times. I’ve asked for a promotion within a month of entering every job I’ve had because I know I have so much more to gain than to lose.

    I never realized I had this much mobility. While I’m gaining confidence and momentum, I’m having trouble seeing beyond the horizon. I know I’m never going to leave the legacy I’m striving for on an hourly wage, even a high one. If you’ve got 15 minutes after you talk to Ken, I’d love to hear from you.

  53. Has anyone successfully demoted or reassigned themselves to mitigate risk and still participated in growing the company?

    I started a CrossFit training facility while finishing a Master’s Degree in Public Administration after a 7-year military stint.

    Three years in, we are now profitable and I have realized I’m not the right person to run the company. I enjoy and am good at our marketing and attracting new clients. I am horrible at running the business on a daily basis.

    Has anyone successfully stepped down from a President/Owner role while still being involved in the business?

    I see several major sources of risk.

    Lost opportunity:

    1) If I continue to lead, the business will suffer from inefficiencies.

    2) Running the business when it isn’t my strong point will keep me from doing what I’m really good at.

    Avoided Threat by maintaining the status quo:

    1) Nobody loves my business the way I do. Giving someone else power who might screw it up scares me. This industry is littered with failed companies.

    2) Starting this was really hard work and I don’t want to lose everything I’ve put into it.

    The answer is finding the perfect person who will care MORE about the business than I do, be strong enough to stand up to me, and drive it into breathtaking levels of success.

    Since I don’t know that person, how should I proceed to balance the risk of lost opportunity with avoided threats?

  54. HI, I was a Realtor who did very well during the boom. However, I always read about online companies and wanted to start and own my own. In 2010 I moved to Goa, India because it was a cheap place to live, I loved it and thought it would be a good place to start my own online business adventure.

    2 years later i am doing freelance work for other US real estate companies and earning an ok learning.

    in the next 60 days I want to start marketing a product(s) to India online. I have been studying how their culture works and think I have an idea on how to market to them.

    The risk involved will be that I have to come up with the money needed to make this happen out of pocket. I have a small amount and am willing to take the risk.

    My dream and why is very strong in my heart and I am willing to risk it all for it.

    The great thing about India is that I can live on $600 a month here. So if what I try does not work then I can do some freelance work, save up and try again. I am not giving up folks. Living over here is challenging and lonely sometimes. But I am finding ways to stay positive and happy, since both are a choice.

    I would love some feedback, tips and help to make this company really work!


  55. I know it might seem cliche this far down the page, but thanks guys.

    This post couldn’t have come at a better time, I’m just finishing up a 3 month contract at a start-up, it’s my first job out of college that i ever been excited about, and I’ve learned more in three months then the last year and a half of working stable “pay the bills” jobs. It has an amazing team with great ideas, and every day I come to work wondering how I manged to get hired by a bunch of people that by all measures should have been smart enough not to hire me.

    My buddy and I were eating burgers yesterday, and he asked me about my job, I mentioned that I my contract was up soon and I had no idea if it would be renewed, he looked at me in shock.

    ” How are you so calm?”, he asked. I didn’t have an answer, and I’ve been wondering, why I haven’t been worried . reading this, it dawned on me, If I keep my job, I get to keep learning from people I admire and growing. If I don’t, I still have those contacts and experiences, and I get to find another risk to take, and even if I learn half as much as I did at this job, I’m still that much closer…

  56. This is a post that I think I haven’t known I’ve needed for a while. I’m browsing HackerNews when I see “How to Take Intelligent Career Risks.” As a 21-year-old college student, I figure I didn’t know enough about the world that I could say I should pass the article by. So I read.

    And when I get to the end, I have a couple of reactions. First, there was a knee-jerk response: “but it’s better to be safe than sorry.” Possibly far more than evolution, this had been programmed into my psyche at a young age by my parents, who are both very cautious (and, I should add, pretty successful) people. So naturally, instinct took over and I discredited the article – after all, there *are* plenty of dangers in the world, and if being cautious avoids one, that’s one potentially crippling or lethal pitfall avoided.

    On the cusp of hitting the “Back” button though, a second thought took over: “What if, by simply letting this roll off me, I’m doing exactly what the author said? I’m too blinded by living in my comfort zone of casual Internet perusal that I can’t even dare to be daring.” Thus, here I am, posting now. I am so very often a wallfly in the great spaces of the Internet – quickly checking in, browsing around a site or article, and checking out – but for a brief moment, a what-if moment struck me. If I passed up this opportunity to take a small risk in the most head-on discussion about the very thing itself, who’s to say that I could ever break the cycle in my life?

    Indeed, I would be lying if I said I weren’t a little anxious typing. What if I DID end up receiving a call? What would I do? Hell, I don’t really even have much of a career to improve. But I think a part of me realizes that it isn’t about getting my post chosen for a career improvement session; it’s about actually going out to write the thing. That’s the sneaky wisdom of this article.

    And I can’t pretend that having the courage to step outside of my comfort zone and write a comment response on a website is anything but a tiny step step towards bold confidence. But it is a step. And one step proves that more can be taken, and that cements something in my mind.

    So let this post be a testament to all who read it that I took that step. Proof to you, and infinitely more importantly, proof to myself.


  57. What risks am I thinking about taking in the next 60 days?

    I own my own retail, service based business with 5 part time employees. We’ve been in business 4 years, barely scraping by. A year ago, we changed locations, and we have increased our client base 500%. We are awash in cash. Cash in my bank account that I’ve only seen on a spreadsheet in my ‘business plan’ telling me what would happen 9 months into business.

    I have an opportunity to open a second location, 20 minutes away, in a different market.

    Do I take these retained earnings, double down, and go multi-location? Or do I focus on my cash cow, shore up my finances, invest in what I have and try to make my one shop as great as I can?

    Risk Assessment:

    Staying with one: Anyone can open up a competing business in my trade area at any time. I have no franchise rights, and barriers to entry are low. That said, I am one of the most experienced operators in town, and could probably maintain current levels of profitability for a year even in a worst case scenario. In one year, I could be debt free and have six figures cash in the bank in worst case scenario while staying put.

    After 4 years, my learning curve has flattened, and I am more or less “minding the shop”. My job is great, but getting boring on a day to day basis. If the worst does happen and my business goes under some day, what skills will I be able to take to my next business and/or job other than “operator of FAILED such and such business”?

    Expansion risk:

    Role change: My role would change from operator to much more of a manager/CEO role, as I would have to grow my team to include GM positions for each location, and would have to invest more of my time in my team rather than my clients, as I have done so far. Do I have the skills to be successful in a new role? Or will my lack of experience cause me to sink my entire business?

    Financial risk: The rent on the second location is more than on my current location, but my business as it stands now could pay it with current profits even if new location had zero revenue.

    Launching second location would cost into low six figures, but majority, if not all, could be cashflowed from first location.

    Time Risk: Have told my wife that we have just got to buckle down for ‘this season’ to make it with our business… For 4 years. Now that we have ‘made it’, I’m preparing to buckle down again in hopes of….bigger payday? 2 young children under 3 and one on the way means time with my family is precious.

    Current thinking: My wife is very excited about the second location, and told me years ago, “We will never have piles of money. As soon as you get some, you’ll invest it in your next idea.” She knows me only too well.

    I believe that a second location would enable a MUCH more dynamic marketing and branding opportunity which could serve to create a defensive moat around my existing business, as well as create a source of potential employees and lifetime customers (my first location is in a very affluent area, and the proposed second location is at the local HUGE state university)

    There would be the opportunity to tap students who are studying my area of business as well as marketing, design, video production, etc as low cost labor for branding, marketing, and employees.

    Many of these students will graduate and move to the neighborhood where my primary location is, and we can retain those clients as they transition into their careers.

    The fear of mismanaging my new role of CEO/manager is also excitement over getting the opportunity to steepen my learning curve and gain those skills, skills that will transfer to any future businesses or jobs, making me much more valuable, to myself or others.

    Even a modestly successful second store will enhance the business of my first, and pay for overhead payroll costs of additional admin and marketing personnel, strengthening my organization.

    Multiple locations meaning multiple teams with interchangeable parts diversifies my reliance on a small number of key employees, allowing me to lose those who are currently key without suffering too much of a hiccup, while allowing me and my family to go on vacation on a reasonable schedule, previously unheard of.

    In a best case scenario, we will reach all of the same financial goals that we have personally within the same timeframe of six months, but would have 2 profitable locations instead of one, creating a more stable foundation.

    Negotiation on rent on second space is ongoing, but the opportunity for 5-9 months of free rent is a real possibility, giving us plenty of runway to build our business and screw it up without screwing up fatally, as operating costs prior to rent will be under 50% of profits of location 1.

    I tend to take on the risks I can identify, and thus manage. In this scenario, there are the risks of the LT liability of the rent, the organizational risk that comes from doubling the size of my organization, and the risk of running myself into the ground by not creating the systems and structure needed to make this jump.

    By standing pat, I can save and conserve cash, which is seemingly the wise choice, but I feel like I’m standing outside in the cold naked. I’m vulnerable to entry into the market by an unknown competitor with large resources that would change the value proposition of my business. I would not have any idea until it was done, and pivot time would be short.

    What would you do? Remember. This isn’t fake money. This is more money than your parents EVER made. The only constant is change.

  58. Hey there, this is Bruce Wang and I manufacture and market US-made table saw safety equipment that is distributed in 200 retail locations worldwide. For the last three years I’ve been working dedicatedly at growing my family business and creating a wealth plan for my family and myself. At 26 years old, it a blessing and interesting position to be in to become the breadwinner for the family and the business growing our revenue and profits over 100% in the last few years. I’ve certainly met with many struggles internally to grow our operations from a work culture/family dynamic standpoint but also from an opportunity cost standpoint.

    Being young, talented, and ambitious presents someone with many opportunities to potentially make a larger impact on the community, new ventures, and the world other than a woodworking business. However, whenever “shiny things” tempted me I always would think back to the story of “acres of diamonds” and stayed focused and harvested…so essentially taking career risks and business risks within my business and industry as opposed to jumping ship into unknown territories.

    But it has reached a point (even though we’re positioned for continued growth) where the internal dynamics and culture of the business and family are hurting. So in many ways it felt like I failed. Failed to make it work. Failed to find the resolution. Failed to change myself to be the right person to champion our team. However, it ultimately set me up to learn the biggest lesson I needed to learn that could have only been learned this way: humility.

    Over the last three years it has no doubt been an unmatched learning experience. The opportunity to become the linchpin in my organization, champion product launches and marketing campaigns, build an infrastructure for our sales force, forge stronger relationships with all our clients with little experience out of college has been the best time of my life.

    So enter the transition, and how to make an intelligent career risk…essentially moving from a business I had a deep domain knowledge of to one I know very little about, fast-moving, and with ever-growing market potential: mobile app development (thanks to Chad’s post). Armed with confidence, salesmanship, and an idea…I’m taking my newfound skill–humility–into new territory. It already “feels” risky baring this much on this post but hopefully many will gain new perspective from my post (I certainly am). And to be honest, it doesn’t feel too intelligent but it feels right.

    So there’s the risky part…going into a new industry that will challenge me, completely change my lifestyle, and convince myself this is an act of inspiration and not hubris. And leaving a business that is profitable and work I love in the name of preserving my family. The intelligent part…taking the skills, the network, the mentors, the drive, the vision, and a plan coupled with a no matter what attitude to win at a new game. So I can be like MJ coming back wearing the 45 or Steve starting Pixar. Both ways, new lessons need to be learned and new habits need to be formed. Thank you Tim, Ben, and Reid for the opportunity to share.

    60 day timeline: smooth transition out, no loose ends, connect with influencers in the app/media community, launch profitable apps.

  59. Hello, I have been obsessed with the 4 Hour Workweek since my husband brought the book home about two years ago. Prior to that I have been a stay at home Mom for 8 years. Two kids, two dogs, and an Air Force husband has kept me from taking any personal risks regarding what I want for myself.

    I have spent most that time of course raising the kids but also fantasizing about all the things I am going to do to change the world.

    Over the past year I have been working on my muse but have yet to bring it to the market. I feel like I have tried to get my leg over the fence many times and each time I try, my foot gets stuck in the chain link.

    My goal is to have my product ready by September 1, 2012 to be sold to the public. My biggest fear is that I am not an expert in marketing and that I will fail to get my product into the children’s hands that so need it. This is my biggest fence yet. Because now it is not about me it is about them.

    I would love the opportunity to speak to both of you and get some insight and advice. And if I win I will bake you both some kick ass biscotti! And Tim too, of course. (Baking is another passion of mine besides reading Tim’s Blog) .

    Thanks for listening


  60. Thank you Ben and Reid for a great post. The resiliency concept reminds me of something I discussed in a term paper on defining “sustainability” in environmental issues and public policy. I argued that a system must be allowed to temporarily operate under unsustainable patterns in order to adapt and grow in response to environmental stresses. I can email you the paper if you like.

    I’m currently 6 months away from graduating with my MS in Environmental Engineering at UC Berkeley. For four years in undergrad, I followed the path of an engineer in training. I majored in civil engineering, and pursued internships in civil and environmental engineering.

    But last summer, I got involved in a software startup with a professor and a fellow student. I failed to get a civil engineering internship, so when my friend offered me a chance to get involved with mobile app development, I jumped on it. It sounded fun, and it was different from anything I had ever done.

    I discovered that I had a knack for business development, product development, and coordinating people. I felt alive –even though the startup has never been quite profitable, getting involved woke up a part of me I never knew existed. At a UC Berkeley Entrepreneurship Association event, one of my friends introduced me to the founder of Noah’s Bagels as an “entrepreneur.” I thought, “Do I really have what it takes to be an entrepreneur?” And just this May, I pitched a business idea to Randy Komisar (one of my life inspirations), and he said KP&C would be interested in investing if I could build up traction.

    I’m stuck between two appealing choices: My planned career goal of going into environmental engineering (I’ve invested years into this) vs. pivoting and running into the world of tech startups. I love working with programmers to develop software (I learned project management from my engineering work) , but I fear most companies will not hire me because I am not a rockstar programmer (it’s a risk for them). Furthermore, my software startup still hasn’t gotten off the ground and I see huge risk in sticking around rather than finding a “real” job.

    I still enjoy environmental engineering work. Right now, however, the excitement of startups and the uncertainties of entrepreneurship excite and enliven me. I’m worried that if I venture into the startup scene, future employers in environmental engineering might treat me as a pariah. They might ask me, “Why did you go into software for 5 years, then decide to return?” Furthermore, they might not hire me because of my years out of college; I would possess the experience of an entry level engineer, but I would be older than an entry level worker (companies generally correlate pay and age). If I go into startups, I would be taking a huge risk (and possibly going broke), and potentially damn my future prospects in environmental engineering!

    Not sure what I’ll do –but it’s a lot for me to think about.

  61. My risk management programme. It’s easy to learn and all too easy to forget so needs looking at or listening to every couple of days or so but it works.

    Step 1

    Risk is as much a part of change as oxygen is part of water.

    Step 2

    Death arrives on its time scale not mine.

    Step 3

    He who needs the least has the most.

  62. Hi, wei here. 24, living in : everywhere i can find a job, currently Springfield,OH.

    I’m a Habachi chef(a year), was a waiter(3 years), own and closed a chinese togo place(9 months ), came to U.S. 5 years ago, stuck in restaurant mainly because of 100,000 debt( to immigrant here), I been working my ass off since.

    Feb 2012, I started learn code @Codecademy,now I’m on Udacity,finished CS101,and CS253, web application development, Hope to become a web developer, run my company and live with freedom . #4HW

    What I want to make in my career in the next 30-60 days ?

    1. I’m moving to SF on july 20th— get out of comfort zone, make uncomfortable decisions .

    2. keeping my job as a Chef, learn code,build project.

    Risk : 1. don’t know if someone would hire me, no experience ,no degree.

    Risk 2. takes time to build a new career,but i need money –I got a 30 years monthly mortgage 1000USD back in china,I try to persuade my dad to sell,but failed)

    Risk 3. If I don’t move, I will likely doing this job for another couple months

    My planed solution :

    1.keep learning, build stuff , do some free works for people,build network and show my works to potential employers.

    2. Less is more, live frugal, earn 1800 a month ,I’ll be fine as long as i becoming good at coding.

    3. Convince Tim : this is the most thoughtful comment and win the mentoring (it will rock my life !) I think i will make a nice 4HW case study : )

    Conclusion : There are Risks involved in everything,the riskiest thing is to take no risks.

    1. Tim, this is the most thoughtful comment :

      After seeing all these comments,I figure I need a simple version,I know what I been through is nothing but if I got the mentor from Ben and Reid

      Here are what I would do:

      1. Update my LinkedIn profile, list Ben and Reid as my mentor

      2. Persuade Reid re-read 4HB, try slow-carb-diet .

      2. Through their network, get in Hacker School NY or Fly to SF right away, meet the people suggested by them,work for them if possible,learn as much as I can.

      3. Build a blog, update: what risk am I taking, what the result of taking it , what am I improving, learning, who got me hire, how much I earning ,hopefully inspire more people to do the same

      4.Give two signed copies of The Start-Up of You to Your reader(I got kindle version already)

  63. Hey, I’m Bobby. I’m a 26 year old awesome fellow. I quit my job over 2 years ago now, and have been travelling the world since working on making my business produce tons of value and products.

    In the next 30 days, I’m actually applying to a few companies where I am now, which is Vietnam, for positions I know I can create huge boosts of change and revenue in.

    One company I’m applying to is a school to teach business topics in. I went a little crazy in my cover letter, and structured a whole new revenue stream for them in the way of online membership site that students can use to extend education or take courses on.

    The membership can be used to create hybrid classes online+in class, and even online classes delivered to students in their busy lives at home. Which is done by a ton of schools, but personally, I think it’s done badly in my experience with these courses.

    I never imagined myself applying to work with a company again, yet, I want to make contacts and transform businesses here.

    The other opportunity in my own company I’m taking is helping entrepreneurs launch their products and services. I’m working very closely with some folks and helping them get their websites and membership websites going so they can start producing income from their great products.

    “What Risk?”

    I’ve taken so many actions that were deemed crazy and risky by people, that I’m really excited with my chosen path.

    I quit my $67,000 job with great benefits (6-7 figure benefits in the future), when I didn’t really have any true plan of what I wanted to do other than travel the world.

    I know I wanted to help people, so I worked on learning and creating products to help people in many different ways in life.

    If I stayed in my job, I know in a decade or so I would probably die from stupid reasons.

    The risk I’m viewing here, is as opportunity. I really want to help businesses succeed and improve, and a lot of the time I’m doing it for free, like you guys, just to learn more and more.

    I personally don’t know exactly what will come out of these choices to say yes, yet I know my life will always be better because I put the effort to helping other people.

    This article was great by the way, I really hope more folks afraid of “risk” read it.

    Thanks Ben and Reid!

    With respect,


  64. I am still getting my head around the fact that I can be brand me, and I don’t need to be the next “big thing” so now that I have done that, what is my 5 year plan ? How do I get to the next step of me?

  65. I am starting a job with Citibank doing commercial banking in about a little over a week. I just graduated college without a degree in business and am feeling like I am being thrown into the fire. I am being sent across the country to NYC for training, and I literally have no idea what I am getting into. My risk is going to be learning all the skills needed and to make as many contacts while I am there, both within Citibank and influential people living in NYC.

    I can be a bit of an introvert at times, but I know that there will be a tremendous wealth of knowledge at my disposal while I am there. I know that I want to be an entrepreneur at sometime in my life (or a second job after hours), hence me wanting to meet other influential people. I am a bit scared though; I would love to get in contact with people who are much wiser than me and try to gain from their experience, and eventually find a way to pay them back, but I always get nervous to seek these people out. I don’t know why, in reality I have nothing to lose, but the mind is a funny thing. I guess that is why I am writing this post–I have never commented on a blog before, but I am hoping that there is some small shot I can get in contact with Ben and Reid and learn from them.


  66. This is really great – love the comparisons to our ancient ancestors and how natural human behavior is involved in our actions even today!

    For me it’s not about just taking risks for the sake of taking risks. I enjoy risk taking, however it has to be EDUCATED risk taking.


  67. Four years ago found me sitting in my big office, doing my big job, but feeling miserable. I was an art dealer, a job, I was constantly reminded, many would kill to have. But after accomplishing all of my goals in the art world, I yearned to express and support my own creativity.

    An off-hand remark by a friend, “Its days like these that make me want to sell it all and move to the south of France,” led to a radical response. I did. Quit the job, sold everything I owned, got down to a few suitcases and moved to the french countryside by myself. Oh, I don’t speak french.

    This self imposed exile was terrifying and then exhilarating. Eventually, reality came a’knockin and I had to find a way to survive, I missed my peeps, artists, but resisted all offers to sell art again. Instead, I created a workshop for artists, teaching the business of art. As I continued to travel, I taught artists how to take control of their careers, navigate the art world, and sell their work.

    It’s been a simple life these past four years but now I’m ready for more. I want to share what I’ve learned in a larger way. I want to offer my workshops for artists online, to sell a comprehensive downloadable program that will help anyone who wants to understand the art business and undertake the real responsibilities of being an artist.

    Because I took a great risk in forfeiting a career, it should be easy to risk starting a new one. But the obstacles are huge. There is the learning curve as to how online businesses work. There are financial risks, I’ve never had to raise money before and am using my last few pennies to get this off the ground. If it doesn’t work, I’m unsure what I will do. All around me people complain,”You’ve had your fun, it’s time to get a real job.” But after four years, a real job won’t hold me. It’s got to be on my terms. I’ve gone feral. I need to summon the courage to hunt the resources I need to make this career move, to start again, so that I can help others who want to do the same.

    1. Awesome story! What you have done is really inspiring, thank you.

      As a hobbyist artist and a web nerd, if there’s help I can give with navigating the wild web, do reach out (this isn’t a pitch, but an honest offer to help. 🙂 )

      Best of luck to you! You are doing great things.

  68. After being forced to study a degree I do not like ( in Pakistan you often dont get to choose what you want to study) , me and a friend of mine are thinking of taking a year off of college and starting our own business. We plan on creating a student companion sort of tablet pc and digitizing every aspect of classroom application.

  69. Last year I needed a change. So I told my boss “I intend to move to Paris or Madrid next year”.

    His initial reaction was surprise-normal response I think. Then he said, “Okay, Julia. So where are you moving and when?”

    This was the hard part – I got freedom. Another, more senior manager, even tried to make it more difficult by asking me why I wasn’t moving to Milan… At the end of the day I flipped a coin, and now I’ve lived in Paris just over a year. I figured if I wanted to flip the coin again and say best out of three after the first time, I’d have to go with the other option (Madrid). If I was happy with the outcome, then I should just get organized and move.

    Now it’s time for a new change/challenge-change and challenge are synonyms to me. For one thing, I already kind of have a new job lined up at the company I’m working for. Yes, I changed position/team when I moved to Paris, which was completely unrelated to the relocation. But since then, I’ve realized what stimulates me, and I’ve been telling people what I want to do. 4 weeks ago they announced that a position, basically what I’ve been saying I want to do, will be created. It will be open for applications, but the profile seems tailored to me. I don’t have the biggest ego in the world – a handful of people in the office said to me “But Julia, this is for you.”

    The thing is, I also want to start my own company on the side. The aim is not to diversify my risks, although after reading this blog I realized I should have thought about that. The aim for me is to grow as a person, and perhaps even to fail. Life is too easy, and I definitely need to start setting the bar higher for myself.

    Risk? To me the risk is that my mother is disappointed or disapprove. Aside from that, there is none. I don’t care much for things, so losing things won’t shatter my life. And no matter what happens I’ll still be me, which is a pretty cool starting point.

    What my company will do? Well, in my view France hasn’t really entered the 21st century yet when it comes to IT, payment services, banking, etc. That is great – that leaves all the more room for me to improve things. I’ve started registering domain names, I know exactly what my first venture will be and have gotten in touch with some guys that have a similar business in another country. That’s all I’m saying for now!

  70. Coffee, Tim. Really AMAZING coffee!

    We drink copious amounts of it. My dream is to rid the world of the freeze dried bland and start a fresh gourmet coffee revolution across the globe.

    Think, for coffee. Freshly hand-roasted coffee, delivered to your door every month.

    I have an amazing coffee roaster in Glasgow in the UK ready to go, the geek skills to build the site, the contacts and experience to raise awareness and grow the sales (I think).

    Here’s the kicker – I work full time. For all intents and purposes it is a good steady job. I’m not sure I like good and steady. I would love to be a truly successful entrepreneur though this will mean risking my steady job and steady income.


  71. Introduction:

    I worked as a consultant and risk manager at a bank for in total 6 years. Decided to take a sabbatical to travel through South America end of last year, which gave me a lot of time to think and be inspired.

    The plan:

    Go (back) to Peru (flight:18th of July) and set up a life there. I have some savings, but at some point I’m going to need money to survive. I would love to try out different things: Freelance risk management work, freelance consulting, teaching, doing workshops, writing (finish the book I’m working on, blogging, other writing opportunities). Perhaps other things that cross my path. -Anything- but get a 9-5 job.

    The risks:

    Not being able to fit in with the culture. Not being able to build a network. Lack of focus (trying to do too many things at the same time). Procrastinating. Stopping myself because I’m afraid I’m not good enough.

    The rewards:

    Doing something completely new. Learning loads of new skills. Finding out which things I truly enjoy. inspire.

  72. I love words! The word ‘Career’, for example, is an interesting one! I think in relation to my own experience ‘careering’ is more apt – The Verb can mean: “To move swiftly and in an uncontrolled way in a specified direction”.

    The Specified Direction? Well, having worked relentlessly at developing a small business, I suppose I’m still hoping to see the following signs along the ‘the specified direction’ of my life’s path:

    -happiness and well being,

    -fulfilment and positivity,

    -healthy challenge and renewal

    To the chase (and challenge!), 4 years ago I wrote 30,000 words of an EPIC story – it’s an ancient Irish myth which I’d been retelling, full of gladiatorial battles, giant adventures and phenomenal cultural insight (hope I’m not overselling it here but think ‘Ben Hur meets Braveheart with real irish accents!’).

    The problem I have is since then I have lost nerve, belief and focus in my writing (It’s sad, given the feedback I’d gotten back then!). I suppose with a beautiful son, a fantastic lady (wife) in my life and a ‘roller coaster’ small business which I’ve been ‘taming’ for seven years now, I can’t seem to get in the zone to finish the book.. (or indeed properly taming the beast of managing the small business – it’s small and yet SO time consuming at present!)

    In regard to the challenge, I genuinely believe this could be one of the greatest stories ever told but only if I can get my focus. I am worried sick that I will upset the apple cart in the process (Tim – your insights on writing have got my juices flowing again!). I really want to make wine and not ‘hooch’ on this one so I must find clarity and focus!).

    I’m teetering around saying ‘Yes’ to my inner guide and to commiting to delivering a draft by Summer’s end (60 days). My challenge is to manage my busiest period of the year at work with possibly the only opportunity I may get to complete this writing project (Long story but re-structuring our home life means papa bear may be foraging for more food out in the forest come September!).

    I would love to share this experience, this journey and this story more with you as it unfolds – I hope at the very least someone else out there in the blogosphere gets a little kick out of seeing someone else with a similar predicament – I’m so close to jumping into the river and striding for that far shore because I’m hungry enough to do it – I’m just hopeful that it’s the right decision! Thanks for the opportunity to share :O)

    John B, Co. Antrim – Half Mystic, Half Wrestler – So my good lady tells me :o)

  73. I’m a freshly minted academic and recently began running training groups for the public. What I am currently offering is very ‘samesy’ and doesn’t do my skills level, or my creative side, justice. In the next 2 months I’m going to ‘style’ my training so that I’m using my skills and targeting my specific audience (university students).

    The key risk I’m taking regards my academic reputation. I want to find the balance where I research, teach, and provide training in an honest, authentic way. There is a risk that my colleagues may perceive this as ‘selling out’. However, working with people is the most rewarding part of all these years of training and research, teaching and training all support one another.

    I think developing my own style and creating a highly personal career is filled with risk. To be flexible and creative there is always the chance that certain things won’t work the first time.

  74. Great article!

    Introduction: Freedom Fighter & Micropreneur. Canadian hanging out in Singapore.

    Career: I want to quit my day job completely in 60 days and support myself purely on my micro-businesses.

    Risks/Perceived Risks:

    – Lack of medical insurance

    – Not enough income to support myself

    – Lack of experience in running my own business


  75. At 20, I’ve just recently taken the biggest risk of my career / life by moving out to California to pursue a career in the music industry as a producer. I had no plan coming out here but found myself enrolled in the LA Recording School as it didn’t make sense to drive 3000 miles to deliver pizzas. My father is sick, and I’m on the brink of leaving.. one of my 4 roommates almost got into a fist fight with me the first week I moved in (he’s drunk off vodka on a nightly basis), our apartment constantly smells of rotting food and dirty dishes, so I’m forced to clean up after people nearly a decade older than me just to maintain a semi-normal lifestyle. What’s worse is the blunt realization that the industry I’m getting in to has next to no “good paying” work. I’m currently being instructed by one of Dr. Dre’s previous mix engineers who picked up the teaching gig because there wasn’t enough money in the music industry to support his family. I’m bleeding money and getting less than 10% of the work done here in Cali than I did in Wisconsin, but am trying to stay positive, maintaining a 3.992 in my current classes. This was a hell of a risk for me, searching hard to find a way to make it pay off.

  76. This year I will reach the position in my job that was always my goal. I will be the General Manager of the cinema in my hometown. I started working there seven years ago, when I was 18. Now 25, being lined up to take the job I always aimed for doesn’t feel the way it should. But I have a two year old boy, and I love the town I live in. It seems right, safe, stable. There are perks. I love the staff, and the benefits (free popcorn and movies!), and an ever-changing atmosphere that changes with the titles. It’s like my family there, and our small coastal town holds no other big opportunities. But I want to raise my family there, and I can picture my boy Archie having a great childhood with his mumma the boss of the cinema…

    However, about 18 months ago I read the 4HWW. It changed everything I thought about how I was supposed to live my life. I had always felt in the back of my mind there was more to life than the 9-5, but I never had the impetus to change. After reading the book I started up a business. It was very profitable, very quickly and soon after starting it we were able to automate it and buy one way tickets to Thailand. We stayed away for 4 months but in the end, the niggling idea that I had to come back and “re-claim” my job at the cinema won over. My business was trend based and so after a great run of over a year it is really winding down. And at the same time, the cinema job looms ahead as bright, shiny headlights that I’m frozen in. “It’ll look great on your resume” they say. “It’s the best job in town” they say. “You’re only 25, it’s a great achievement” they say.

    But all I want to do is create. Right now I have two new projects I’m working on, one which involves a lot of overseas travel (win!) if it comes off, and another that I’m in very foreign territory with so I’m learning tons. And I just want to keep going with them. In my heart I know I don’t want to work the 9-5, stuck in one place job, where my decisions and creativity are kept on a leash by Head Office. But my lizard brain is having trouble letting go. I’m really passionate about both of my new projects, but I just don’t know how I’m going to get the customers I need to make them successful, and therefore can’t feel confident to leave the “secure” job.

    My main thought that I come back to is this: If my two projects do not come off and I turn down the secure job, how long can I keep hoping to “make it” on my own, with rent to pay and a family to support?

  77. This was a wonderful post; great read. I’m taking a risk just by posting this comment because as I’ve skimmed through everyone else’s comments and I didn’t see any story similar to mine & quite frankly, maybe mine won’t be interesting to anyone else but I always look back at my life and try to keep myself inspired by it. I’m currently typing this up on my iPhone because I cannot afford Internet at the moment, however, I have a strong sense that things will change for me soon.

    I am a single mother of four who, until last week, was working in clinical research & going to school for nursing. After reading Tim’s four hour work week I allowed myself to accept the fact that I was completely miserable at my job and unsure about my degree choice. I knew that becoming a nurse would be a sound career choice & would help me excel in clinical research but other than for those reasons I had to stop and ask myself, “Is this what I really want for my life?” Well then, here comes one of th riskiest choices I’ve ever made. I quit my job (as gracefully as possible because I really wanted to tell my boss how much her presence makes me think of Satan and his minions but I kept my cool) and I switched my major. I don’t really have some wonderful plan set in place & haven’t stopped thinking about how I’m going to support my family however I didn’t let that get me down or stop me.

    Just for a little background maybe I’ll share a little bit of my story and how I’ve inoculated myself & mentally prepared myself for this kind of shock because honestly, just about everyone I know is freaking out asking me, “what are you gonna do? What are you gonna do?”


    – Pregnant at 14, mother strongly suggested I have an abortion: done.

    – Pregnant at 15, mother strongly suggested I have an abortion: not done.

    – Dropped out of high school. Struggled to take care of my son alone, abandoned by father (son’s & my own)

    – Got tired of the B.S. got back in high school, while working & taking care of my son alone. Graduated on time.

    – Pregnant at 19, moved from NJ to FL to live closer to my mother. Had daughter, went to school to become medical assistant while working 2 jobs then when my daughter was 9 months old, got pregnant again.

    – Ended up having to go into a homeless shelter with my son, daughter and “belly”

    – Nearly miscarried my son causing me to be on bed rest, forcing me to quit both jobs & take a medical leave from school. (I nearly lost mind then.)

    – Had son, finished school, started working in clinical research office, gained a wealth of knowledge & developed a love for research.

    – Met someone, got out of shelter & got married for the 1st time.

    – Pregnant at 25 (this one was planned). Had my son.

    – Husband turns out to be a child abuser & pedophile. Husband goes to jail.

    – Within a month, I quit my wonderful job, move to central Florida with me, my 4 kids, my best friend, her daughter, my mother, her 2 dogs, our cat & NO JOB.

    – Even with 5 years experience & certification in clinical research, couldn’t find a position in my area. Took on a job at call center.

    – Finally found a position in clinical research. Also, found out who I was working for (please see reference above)

    – Mother gets diagnosed with MS, have to take a temporary leave from work, sell all of our belongings & move to NJ with kids, mom, 3 dogs & our cat, not knowing where we were going to live or how I was going to make any money. We moved in hopes of having a better chance of getting mom some health benefits. After three, very difficult months, moved back down to FL but still currently, taking care of mom financially.

    – Read 4 hour work week, quit my job, switched my major to liberal arts, with a desire to become an interpreter for the deaf.

    So sorry if that was too elaborate for this kind of post but I wanted to get the picture across about the difficulties I’ve encountered and why I think I’m not completely freaking out right now. Here I am, a week later and don’t have one wonderful idea that I’m working hard on & hoping that it works, I have several thoughts that aren’t well put together & would greatly appreciate some mentoring.

    – I’m currently writing some fiction stories (my fav, although I have been told that I should write an autobiography, eh maybe one day)

    – I’m selling a few knick knacks on eBay

    – Started selling AVON products

    – Thinking about opening a shopify account

    – Searching for an affordable programmer to get some mobile apps going

    – Hoping that some other muse will strike

    – Trying to teach my children that material things are of less importance & that when you take the “what’s-the-worst-that-could-happen?” view of life, wonderful things can be achieved.

    So there it is, in a very large nutshell and regardless of whether or not I win the mentoring or the book (which I would love to have), I can see the great benefits of even posting this message, it was very cathartic. I wish everyone, including myself, lots of luck in all of their endeavors!

    (P.S. Please forgive any typos, I’m a great speller but typing on the iPhone can get a little tricky at times!)

  78. This makes me think of the Black Swan principles and how to cope with them.

    As long as you ensure you limit your downside (stability) you can expose yourself to unlimited upside (start your own company in your own time). When one of your own companies take off, that is your new limited downside. In that way you get to consolidate your “safe” environment as well as venture into the world of entrepreneurship!

    Great post, really hits home!

  79. “What doesn´t kill you only makes you stronger.” Right? Jim Collins has an interesting take on risk in his new book – Greatness by choice – he talks about the -ROL – return on luck and the importance of getting a good return on “lucky” opportunities. Anyway, I´ve been working at a company that has fairly low pay but great opportunities of learning and networking. HSM is an executive education and management knowledge leader in Brazil, we organize many conferences a year ( some speakers this year: Joi Ito, Kurzweil, Michael Porter, among others), have a magazine, publishing company and business school. I work directly with the Chief Knowledge Officer creating the conference´s program, selecting articles for the magazine, books to publish, etc. I started a company in the healthcare space – HealthCO – taking advantage of HSM´s work with this industry. Brazil has a 15 year demographic bonus (young population) and still don´t face major issues with health but changes are coming to the whole sector and with such a big population (200 million +) we are finding ways to help companies better manage their employees´s health. Have been growing 3 digits for the last 3 years. We are a 4 people company (me and CIO have a 5-9 job).

    Nonrelated: I´ve been trying to reach Reid about a professional speaking engagement in Brazil at ExpoManagement (end of 2013). It would be great to get a direct channel. We already have some major names confirmed.

    Tim – I am a great fan.

  80. – 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 45-60 days I want to have a part-time position lined up teaching for the Fall semester at the college level, consulting small to medium sized businesses at the C-level, or be running my own business; any of these options must be generating at least $500 in additional net income for me within 6 months. (I have student loans to pay!) Some quick background on me: I am 35, have worked full-time for the past 12 years in large businesses – mostly financial services and now a top 3 pharmaceutical distribution company, and just graduated from The Ohio State University with my MBA – a lifetime achievement in my book. I know I could teach at the community college level with my degree, but don’t have any direct teaching background. I know I could consult business owners on how to strategically position their businesses for success, but don’t have any direct consulting experience. And I could run my own business successfully, but don’t have any ground-breaking ideas for what that business should be.

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

    The risk is both non-existent to me, and a very real fear. By this I mean that I know I could set out to accomplish any one of these things and really work hard to pursue it; however, I fear that it might not “work out” meaning that it won’t fulfill the goals I set out to accomplish – namely finding my muse and a solid additional income stream for my family and I. I know I would learn from the experience no matter what. I know that I could make of the experience something successful in my life (I always have with anything I’ve set out to do), but yet I am a perfectionist and dislike starting something that I am too worried won’t be just the right thing for me.

    Help me make this world a better place than the sum of our fears of success!

    1. Ironically, it was the speech at Harvard in 2000 by Conan O’brian that came to mind when I read your comment. I never liked his show but that speech was great. “Your biggest liability is your need to succeed, You need to always find yourself on the sweet side of the bell curve.”

      You have work experience, currently employed and have an MBA. Most people will ask “what do you have to be afraid of?” They might even look at you funny when mention you want to earn $500 extra a month, because the assumption is that you are getting paid well and you shouldn’t need it. I understand there are plenty of reason you might need extra income.

      Teaching can be a rewarding option. However, it does depend on other people to make it work.(the college has to hire you) Also I think if you don’t have a real passion for teaching, it might not be a good fit because of the time and energy it will require.

      Consulting is an interesting choice of both independence and contractual employment. It is you that makes it happen. It could more financially rewarding per the time you put in than Teaching at a college. There are no worries of losing money unlike business.

      Owning a business is similar to Consulting. Only difference is that you own a business which can be sold vs owning a job which you can’t sell. It is a completely black canvas. You don’t need any ground breaking ideas to start. The ones that make the money are the ones who bring things to market anyway. Less stability, your time commitment might vary, and profits/losses are uncertain.

      I would suggest that your fear is one of inaction. You could try all three options and see which one sticks. It might also help to think ahead and consider what you would do if your choice didn’t net you $500 dollars, but put you in the hole? As an academic, I think it is easy to see things in steps. GED, AA, BS, MBA, PhD, law degree and such. So it maybe easier to think if you layout the steps you will take and the changes you will make per outcome. Hope this helped.

  81. I have been a contractor for 3 years and I have been running a side business for the last 6 months. From the 1st of next month the side business is going to be full time, that means giving up the rather easy freelance money I have been getting (£2000 – £4000 a week).

    On top of this I am not going to renew the lease on my flat and plan to live for (at least) with no fixed abode. This is an experiment I have been wanting to preform for a long time.

    So to sum up, no large income, no where to live. Sounds like it’s going to be a fun rest of the year 🙂

  82. I want to turn unresolved New Year resolutions into life changing outcomes.

    I’m 35, live in Scotland, and have 12 years’ experience of launching cultural projects and events. I have a concept for a new business, which I have been carrying around in my head for the past 15 months, which I want to turn into reality.

    The idea: a project which allows people who say ‘I’ve always wanted to…’ to saying ‘I did …!’. Those who have a dream would be paired with those who have already made it happen. In learning sessions, from intimate 1:1s – such as a CEO wanting to pivot to a new sector, to the more public – a group writing the first chapter of their novel together. We would turn unresolved New Year resolutions into real, and potentially, life changing outcomes.

    I know from personal experience the difference this business could have on me and the wider world. The company would help people make the first move. For example, I’ve read many business start-up books, and have collected piles of cuttings that relate to the concept, but I need to actually do something. The initiative would get people off the blocks. For myself, creating a company that helps people move from being passive consumers of content about what they really want to do; to actually doing it is hugely appealing.

    Since October 2011 I have been trying to develop my career with a new challenge. Due to the recession, I have been competing against candidates with more than a decades experience than me. For 60 days, I want to change tactics and create my own job. I would like your help turning my concept into reality.

    In terms of risk, my main worry is that I may not succeed. I also need to make quick wins (such as money in the bank!) to convert the person closest to me who is sceptical about creating a job vs. getting a regular one.

    I hope to hear from you soon, James.

  83. I work as a Drilling Engineer and I’ll make two changes in my life. First, I’m taking two international projects back to back. the first one will be in Cameroon and it will last at least a couple of months and after that, I’ll work in the Peruvian jungle for 6 months. I have never been in any of these places and I’ll be working with people that I have never met before. Also, I’m on stage 2 in starting my third company. the first one failed and the second one is growing slow, but I’m still convinced that I have everything inside me to fulfill my dream.

    The risks associated with these projects are very relevant in my life, because I don’t have experience enough and I’ll be taking a lot of responsibility in an industry where mistakes are not forgiven. Also, been far from home for so long will bring the risk that I might come back and find out that someone else is doing my job and I’m no longer needed here.

    However, I believe that the actual risks are no way near to the growing opportunities that I’ll encounter. I’ll be able to meet new people that have a different culture and live experiences than me, so I’m sure I’ll learn a lot from them to grow as a person, as an engineer and as an entrepreneur, by getting a more global perspective of what people’s interests and needs are.

    Thanks for this opportunity,


    PS: I’m not including the biggest risk of all in terms of my mind stability. Been far from my wife..

  84. I learned about the nature of risk in Cairo, Egypt.

    I moved to Egypt a few years ago with no job, few friends and absolutely no idea what I was getting into. Despite a short study abroad experience there in the past, this was real, post-college life: suddenly I had to live in this place, interact with neighbors, buy groceries and rent an apartment for the first time in my life.

    But the risks paid off. I got a well-paying magazine job, had countless priceless experiences and even met the girl of my dreams. Yet, just when I felt like I was on top, Egypt had other plans–namely, the Egyptian revolution of early 2011.

    I lived through two weeks of anarchy before flying home. Tanks were outside my apartment, thugs roamed the streets and jets screamed over the city. I even stumbled into some of the revolution’s biggest protests, where I was heavily tear-gassed for hours on end, shot at with rubber bullets and nearly trampled on a couple of occasions.

    Now, I’m back in the States and freelance writing full-time. In the next 30 to 60 days, I want to start my own mobile app company. It’s a scary, risky prospect–especially with my limited funds and small (but growing) network.

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

    I remember the crack of rubber bullets, the unmistakable stink of tear gas, the fear and chaos of those two weeks in January. I remember a few times where it really did seem like I might be seriously hurt or even killed, like hundreds of others during those days. I remember the first few nights of the revolution, when the police fled and the whole city went to hell. I stayed awake all night praying I wouldn’t have to defend my home and loved ones, all while the younger men from my building patrolled our block with sticks to keep the thugs out.

    Life is short. Things are (generally) not as scary as you think. I’ve got a lot of fears, but the fear of not doing it all in my limited stint on the planet is what keeps most of them at bay. In the words of a very wise man: “Stay thirsty, my friends.”

  85. Thinking about pivoting a large part of my focus from current 2 year old company to a spin-off that resulted from it. It appears that myself and a very good client stumbled into a sweet little niche with an entirely new market behind it. It’s a huge risk because: 1) why is no one in this little space already? 2) definitely jumping off the beaten path that has stability and better than average promise.

    I’m thinking about the risk as a fun way to solve a bad-ass problem in my space (that will definitely help you at some point in your lifetime) and at the same time do something original, challenging and risky. Whether it flies or flops I’m appreciative of the breath of fresh air it has provided.

  86. Thanks for the great post, guys,, and here’s my crack at this tantalizing contest you’ve devised.

    The biggest risk I’m taking in the next 30 days is to continue on the course that I’ve been on for the past eight months, which have been among the most adventurous I’ve ever lived. Since October, I’ve been learning everything I can about business, web design, programming, and entrepreneurship, and have put the knowledge towards developing several blogs, Twitter feeds, and my own startup. The risky part is that I took some time off work to do this, but now it’s getting to the point where I may have to go back to Plan Z for a bit and regroup. In the next 30, before I start considering mo traditional options again, I want to attend as any relevant MeetUps as I can, promote my ventures through as many media venues as I can, and if possible try to find a truly spectacular mentor. I’ve found this last one to be th hardest, as my network isn’t really geared towards entrepreneurship, but I’m working on it.

    It’s interesting that you ask about how we’ve been thinking of risk. I first came across he word in the context of stock markets, where risk means (roughly) degree of possible failure. It’s useful to think of it that way, but I think it lacks the positive dimension required for successful businesses. People like Reid don’t just want to not fail; they want to have a big impact as quickly as possible. As a result, I’ve come to think of risk in business as something more akin to willingness to face upset in the pursuit of a vision.

    Unless you’re dealing with investor money, the risks in entrepreneurship usually seem to be personal ones, and have a lot to do with comfort zones and scope of vision. While you want to hear the input people are giving you on your venture, you also have to be willing to look like an oddball to your friends and family and coworkers if they haven’t seen your particular brand of awesomeness the past. I think the best thing you can do to moderate risk in entrepreneurial ventures is to gain the good graces of trusted but brutally honest allies, who can give you realistic feedback on your actions (which is exactly what I’m looking for a top-notch mentor).

  87. Wrong. You should not only weigh gains and losses, but also their probabilities. You say that “a risk is good when the possible upside outweighs the possible downside” and your writing echoes this attitude. Does this mean you would accept a bet where there is a 10% chance that you win $100 and a 90% chance that you loose $50? Even though “the upside outweighs the downside,” taking this bet is a pretty bad idea.

    Similarly, just because an engineer has less short-term risk in his/her career than a salesperson, it does not mean that she/he will have more long-term risk. I guess by long term risk you mean an event that has a little likelihood of occurrence, but if it happens, it will have devastating consequences (if not, please define long-term risk). Let us ask ourselves: assuming a “disaster” happens, and both the engineer and the salesperson gets fired (or equivalently, loose all their commissions), what is more likely, that the engineer finds a job more easily or that the salesperson does? I would say that the engineer has an easier time recovering after a blow.

    Mistakes of this sort are hiding throughout the writing. Just to give another example: how do you know that Saudi Arabia has a higher chance to “explode” (whatever that means) than Italy? Events like this have a rare occurrence and it is extremely difficult to assign probabilities to them (and judge which is more likely). Think of the Roman empire, which was struck by blows for centuries, which endured much “volatility” and “short-term risk” (emperors killing each other, Germanic tribes invading the border, rebellions in some provinces, pirates, etc.) and yet, it collapsed anyway.

    All I want to say is that it is highly questionable whether accepting short term volatility does indeed lead to more resilience.

    1. We fully define risk in the book itself and account for the probability point. You’re right that potential consequences is not the only thing to evaluate — you need to think about likelihood, too. The problem is that assessing the likelihood of something is really hard in most situations — despite all the fancy predictive models designed on Wall Street and elsewhere.

      In terms of the short run vs. long run point, it’s impossible to generalize too much, of course. But in general, yes, we’d argue that Saudi Arabia is more fragile than Italy, and that if there were a major disruption of some sort, it has a greater likelihood of experiencing harsher change.

  88. My name is Neal Konesky and I am currently creating the most value-packed personalized nutrition program for business professionals, CEO’s and entrepreneurs. In the next 30-60 days: I will test my system by helping these individuals for free to collect incredible testimonials, input and most importantly happy & healthy people. Businesses run the world. If I can transition to do this full-time and move from my current job I can improve the lives’ of the people that live to run these businesses. In turn the businesses run more efficiently and with better purpose (in theory). Also, in the next 30 days I would like to build up my blog to over 1,000 followers (my goal) so it will be worthwhile to create an online magazine with my blog (differentiation+art).

    The risk involved: battling that throw-up feeling before I public speak to network, substituting countless hours consulting rather than improving relationships with family/friends, potential for leaving stead paying career for a career consulting, writing and helping the people that run the world.

    Just like said above: higher upside is always worth it when it better than the downside. Improving the lives of the people that do so much good for the world – worth it.

  89. Hi, I am Thomas, a 30 year old married man with 3 young kids. This post really hit close to home as I am having a real hard time figuring out if I am willing to take the risk.

    I currently work full time as a purchasing manager/Web Designer for the same company 6 years now. My salary is decent and I provide for my family. But I have always wanted more. I am not someone who could work the same job forever, I love to learn and try new things, pushing myself to improve my skills. I have a huge entrepreneurial spirit. Which has lead me to start a new business last year. This side business has grown every month to where the last 3 months it has made equal to what I make in my day job. My wife, brother, and brother-in-law all have helped me pick up the slack to keep the business moving forward. It has been an amazing experience and my passion is in this business. I want to desperately give it my full attention and see what I can do when I focus on it full time instead of having to split my focus between two jobs. If I was single I would have made the jump and left my current employment to go full time entrepreneur. I have no doubt about this. If I was married I am sure I would have as well. Here is where the risk has me in a standstill and feeling desperate. I have 3 amazing children that rely on me to feed them, clothe them, and overall take care of their needs. When they come into focus all the things that could go wrong seem to be more important than ever. What if I stop growing? What if the business fails? What if a lawsuit happens wiping me out? Then I have to find another job in a market that is difficult to find one. I feel like I will be judged for pursuing my dream and risking my kids health and well being. The fear of being considered an idiot when things go bad is a real fear. But the fear of failing my kids is enough to keep me feeling chained up and working 80-90 hour weeks to make things work. I keep telling myself that once I get more cash saved up, or profits get to a certain point then I will make the jump. But I can’t really be sure I will be able to do that when the time comes. I am torn, and would love any help that you can muster to throw my way.

  90. Critical thinking suggests that a few of the things mentioned in your post are insufficient. So I’ll like to point them out for the benefit of you and the other readers.

    *note: I suggest choosing the winner at random. So many people are vying for guidance, and yet only one person will get it. After reading their long comments, it is a bit sad that the rest would have wasted their time pouring out their circumstances.

    Weighing Benefits vs Risk is a hard concept and you were brave to tackle it. Possibilities by its definition are almost infinite, and it is usually the individual’s perception that dictates which possibilities are included in the analysis. For instance, in your post you included examples of your risktaking paying off and none of your risktaking crippling you. I thought that was lacking of your post, not because it would have made a better story, but it missed a critical aspect of risk which is (crippling) failure.

    Also I disagree in some level that a continuous appetite for risk can medicate future failures. It surely might prepare you better, but risk means no guarantees. You can fail at a part-time job, then at a contractual job, then at a governmental job and finally fail at entrepreneurship as well to be no more. I thought the post implied that early, frequent or continues risk taking is a guaranteed way to success, and needed to be clarified.

    When you mentioned saying “Yes”, I thought of the movie “Yes man” staring Jim Carrey and chuckled a bit. On a more serious note, Tim’s work clashes with your post because saying No to unprofitable clients, constant emails/meetings, large employees, and so on is at the core of what he preaches. It was slightly disorienting.

    Lastly, I thought your examples of being at apple and being on the board of paypal was impressive but un-relatable to the readers. Most people will not get the chance to work at a innovative company such as apple or be on the board of any company let alone paypal. It sounds a bit like chest-pounding. Something to keep in mind.

    If you have read this far, I would like to leave a few titillating thoughts.

    1. What are the benefits of not being on LinkedIn? It was Mark Twain that said “when you find yourself in the majority, it’s time to reconsider your position.” By now so many people are vying for online presence, linkedin and so on that the benefit of not doing those things should have risen. But by how much and what are those things?

    2. Lets say you are not picked for this “prize”. (99% of those who entered won’t) What would be your next move?

    Thank you.

  91. Thanks for the opportunity to learn through this post, and the contest! I live what you describe – defining risk in relation to life threat and valuing nimbleness and resiliency as my most precious career-building assets. I appreciate your mirroring in words what goes on in my psyche.

    My target audience is creative owners intent on having a business that supports their ideal quality of life doing work that gives them energy. Through one of my current face-to-face products, a roundtable model called the Circle of Trust (yes, as from Meet the Fockers), I’ve found how important peer support is to business owners’ success, and how brilliant business owners can be when learning together. Essentially, I’m moving the Circle online.

    Informed by 4HWW, my career goal is to shift from a business model that requires my constant presence for income generation – small business consulting in Kansas City – to one that doesn’t – products sold online using digital marketing to reach and build my market. (My clients call Tim my Author Crush; I’ve sold at least 100 copies of 4HWW and another 25 of 4HB. Thanks Tim!)

    I recently completed Phase I toward my goal with the objective of increasing revenue from my consulting practice to invest in the cost of my plan. Phase I: launched the initial web platform ( your basic blogsite for now, poised for rebranding as market feedback suggests); indexed my archives of content to prepare for commercialization; developed my launch marketing plan; and began digital marketing tactics’ implementation.

    I’m now am at the front end of Phase II to begin generating revenue from online products: 1) package and test market initial info product; 2) implement second phase of digital marketing program to continue to build fan base; 3) test initial version of online Circle of Trust; and 4) begin production on video series. (No talking head, or just another site visit, for this program! I’ll share details about this format with contest judges by email when asked, but I’m not yet ready to publicize.)

    LinkedIn is an integral part of my plan. (No lie. You can check my account activity to confirm I’m not a smoke blower!) I funnel business owner Connections into my digital marketing machine. Each week I send all new Connections an individual message to sign up for my enews with the reward of my free how-to article, “Fees or Famine.” Which drives to my blog. Which leads to the mouse with a cookie…

    LinkedIn also on the shortlist of platforms I’m considering to test my online version of the Circle of Trust. It is obvious too that LinkedIn would be a fitting sponsor for my video series since my audience is one of yours.

    Inspired by 4HWW and nurtured with LinkedIN, this career plan is a poster child for our shared philosophies and visions. While you all already accomplished impact at the level I envision, I’ve proven meaningful impact for hundreds of business owners myself. Our collaborative success offers residual impact for infinitely more. My next career move is not a pipe dream, but a pipeline of demonstrated progress, atop a career of dreams delivered despite humbling missteps. It’s truly the perfect time in my plan, with the perfect combination of allies, to leverage the gift of your prize.

  92. I resigned from my job on June 1 to work full time on a company I started in November. After working for a wealth management firm for 5 years, becoming a partner and helping manage over 300M in individual and corporate assets, I had had enough. Where did the joy in life go? When did things get so boring and why we’re they so complicated? What happened to the 8 year old who started his own shoe shinning company? What happened to the middle schooler who started his own pressure washing business? What happened to the YMCA camp counselor?  Being a doctors son and a brother of an orthodontist, banker and marine this was a big shock. You can’t quit a promising career. It’s too risky my conservative parent’s said. A week later I had moved from a house of 2000 sq ft feet to less than 800 with my cofounder and sold most of my items on craigslist. That’s when reality sank in. WTF did I do? I had been in sort of a depressed gaze for about a week until my brother forwarded on your article. At 27, your article opened my eyes and made me realize I am doing what I love. Taking a risk is engrained in me.  If this doesn’t work, something else will. The corporate life was just helping me die inside.The risk keeps us young and living. I started an equity-based crowdfunding platform that will allow people to help bring companies they want in their community to their community. What could be better than helping others help others and everyone benefiting from it? 

    I realize I may not qualify due to resigning already but thanks for the article. I look forward to the challenges and risks of starting my company.


  93. Hi Tim, Ben and Reid. This post really resonated with me as I was recently given notice that I am going to be made redundant. I had one of those “safe” government jobs and over the past few years a huge shake up has resulted in a cost cutting exercise that has resulted in job losses and out sourcing. I agree that these jobs don’t prepare you for the times when you have to dig deep and do whatever you can to get your next pay check but blogs like this and Ramit’s IWTYTBR have really helped me find the drive to pursue a brighter future. Although I have been forced to make a change I’m viewing this as the kick I needed to take action and start a new career where I look forward to going to work.

    I have no doubt that the next couple of months will be hard work, I plan to network with as many talented people as possible and learn from them even if it means working for free to get my foot in the door. For a long time I feel like I have been just another cog in the machine churning out the same thing everyday but I want to feel like I am making a real difference to the future of a company or project. I know what my weaknesses are and I am facing them head on which has sometimes been scary but I just keep thinking what’s the worst that can happen?

    The biggest risk I face is running out of money before I get a sustainable income, but in the short term I can afford to take higher risk opportunities such as short term contracts or working for un-established startups. I don’t really know what the future will bring but it’s going to be fun finding out.

    Thanks for this great post.


  94. If you can enjoy life as a journey, a process and a set of experiences then interesting things will happen to you before your time’s up.

    If you just looking for an end result, a job title or strong sense of security then you’re just going to be paralyzed with fear.

    The modern world is a playground for those with the first attitude I mentioned and a prison for those who believe in the latter. Have fun, lighten up and get your hands dirty!

  95. I learned about risk the hard way – I spent 3 years at a startup, as their sole software developer, trying to make things work. When the funding ran out I was made redundant, and left hunting for an alternative. I grabbed the first decent job I could find, and was made redundant again for the second time in 5 months.

    This was 8 weeks before I was due to be married.

    As the guys say – That stable career really isn’t ever that stable.

    It was after this that I decided to get more friendly with risk…

    Risk Management move – I took a decent corporate software dev job at a great local company that I knew offerred good prospects, in an exciting industry.

    Risk 1) Started proactively networking inside the company, to find like-minded people to work with inside, and on outside projects.

    Risk 2) Started pitching my boss with ideas to develop innovation strategy inside the company, and managed to get my ideas to board level.

    Risk 3) Developed a startup idea with a colleague, wrote an initial business plan, and pitched it directly to the CEO. He didn’t bite.

    Risk 4) Through my network, I was headhunted to be the Techie Lead at another startup, so I took the job. Risk management move – Took the job as an employee not a contractor so I had stable full-time income to help buy a house.

    Risk 5) Put reputation on the line to approach ex-CEO again, with better business plan – Secured £50K funding without breaking a sweat.

    By becoming risk-agile, I went from 2 redundancies in 6 months to being the top techie with 2 startups – One provides me with a stable income, the other is my baby and is due to hit the market in the next month. I

    Also I’ve nearly tripled my salary, and I absolutely love what I do 🙂

    If I can do it, you can.

    My advice for the risk-ambivalent:

    1) Take risks for love, not money – Take risks to do something you love to do, or something you think will really benefits others – Don’t just go for the big payday.

    2) To steal from Tim: “Beg for forgiveness, don’t ask for permission” Never ask people if you can take risks. This is critical both in and out of work – Don’t ask your family for permission, discuss things but the risk should be your choice. Also don’t ask people diffidently if you can talk to them – Just go for it. By doing this and following Tims advice, I’ve secured investment in my company from a CEO I used to work for, and had a face-to-face chat with my idol, Chris Anderson from TED (in the middle of the Qatar desert).

    3) Don’t hold yourself back for a bull***t reason. It’s easy to justify dodging risk in the name of family, or financial solvency. Unless YOUR risk puts THEM at risk, then be all you can be and go for it.

    4) Own and share your f***-ups. No-one succeeds all the time. Not every risk pays off. Take responsibility for when things go belly-up. Learn from it, and most importantly help others learn from it.

    My next BIG RISK, and what I’d love to work with Ben and Reid on :

    How can I balance the development of my current startups with pursuing other ideas, as I have other businesses concepts I’d like to investigate, validate and hopefully build. How can I go from a singular focus on one business, to multiple, without people feeling like I’m not committed to the original project?

  96. Great article guys, really thought provoking and inspiring.

    My big risk is moving into a completely new area of work. I am 26, worked two years in publishing and last year I decided to take up a position at Hyper Island to learn more about digital technology and methodologies. I graduated in January and have been working freelance and doing placements. This has given me an opportunity to do further training, as well as to give myself time to think about what I want to be doing. As someone passionate about where the world is going, I have taken an interest in food production acknowledging its significance in seeing us become a more sustainable society. My plan is to move into this area, I am just trying work out how I want to be doing this.

    I have been thinking about the risk a lot. What I have been trying to work out is how I am filtering that risk. I realise a lot of my mental prejudice toward this area is associated with my upbringing and what I have deemed an appropriate career path for myself. This past month has been a case of breaking down my ego, understanding myself and trying to understand what I truly want. Having reached some clear insights in the past week, I feel capable of making this jump with a more clear view. In looking forward, the risks involved are a hugely competitive marketplace, dominated by big players whose reach in both distribution and marketing I could never compete with in my lifetime; an increasingly uncertain environmental outlook; and a growing population pushing up food prices. Not to mention that I intend to do this in London (I am from Melbourne, Australia), so I am out of my comfort zone with a very small support network surrounding me. With all of this said, I am excited by these risks as I feel like I am moving in the right direction and moving towards a future I want to live in.

  97. From my experience, risk begets risk. My first real “risk” was choosing to not pursue a career in engineering like all the other engineering majors around me in school. Instead of doing the typical internship for a large corporation, I chose to volunteer my time helping my local church launch a thrift store that benefits the less fortunate and provide on-the-job occupational trainin (okay, they paid me, but it was so little that I felt like a volunteer).

    As a result of taking that risk, I ended up getting the opportunity to help launch a coffee shop that provides for orphan care through coffee development and the privilege of starting my own tutoring company that funds educational development for at-risk youth.

    Though I still provide some tutoring, I am currently employed as a business analyst at a greeting card company. It’s funny how everyone around me is applauding me for finally getting a “stable” job. To be honest, I see it more as a transitional job that pays the bills until my next “risk” takes off (which I am already working on — more to come later).

    Anyways, the whole point is that your first risk may seem huge, but in reality it’s probably not as big as you think. Once you take that first step, you begin to realize the infinite number of possibilities ahead of you. That first risk will almost inevitably lead to bigger and better risks in the future. I know mine did!

  98. Hi guys, my name is Rachael and I am an IP litigator. (Hello? where did you go?)

    In the next 30-60 days, I would like to finish the first mock up of my side project: a website that collects and posts performance metrics for IP litigators. It’s a risky venture for many reasons. First, I love being a litigator and don’t plan on leaving my current job. As such, to the extent “free” time exists now, it will cease. Second, a lot of lawyers are going to hate the site and i am likely to receive heat from my community. But I believe it to be a vital service and will help much more than harm. And the list of concerns goes on….

    Your second question is very interesting. “Thinking about” implies some sort of method. I am not sure I am thinking about the risks at all, as opposed to listening to fears and concerns. Which is uncharacteristic, i would have thought, but your post suggests otherwise. Regardless, I will take the cue implied in “thinking about” risks and develop a method for assessing and working through the fears. And I’d sure love some help with that (pick me, pick me).

    Good luck in your endeavors,