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!:”

Posted on: June 14, 2012.

Watch The Tim Ferriss Experiment, the new #1-rated TV show with "the world's best human guinea pig" (Newsweek), Tim Ferriss. It's Mythbusters meets Jackass. Shot and edited by the Emmy-award winning team behind Anthony Bourdain's No Reservations and Parts Unknown. Here's the trailer.

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572 comments on “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.


    • 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


    • 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.


    • 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


    • 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…


    • @ 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.


      • @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!



    • 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.


    • @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.


      • @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.



    • 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.


      • @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.



      • 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.



    • @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.