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. Great Post!

    I am Vidya, 25 working for a financial advisory firm as an associate advisor. I returned from my first solo backpacking in Vietnam 2 months ago and was made redundant in my previous upon returning to work. I just started this job 2 weeks ago which is a 6 month maternity contract.

    I am loving this job because not only I am working with smart people, i am also earning approximately 20k more than my previous job given that I have only 6 months experience. Although it has only been 2 weeks, I am being pushed well beyond my comfort zone. The epiphany I had after starting this job was, realizing the fact that getting a job after Uni is not the ultimate destination, in fact the journey only starts now for doing amazing things and achieving overall success.

    1) 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)?

    Although it is not quite a change in the next 30-60 days, the change I would like to make is to convince/impress them to hire me on a full time basis after the 6 months – on my terms. My ultimate goal would be to work for 6-9 months in BA, Argentina while travelling South America. Working remotely in the finance industry which is highly regulated is a challenge in itself. But I want to convince them that this can be done.

    So far I have demonstrated my commitment to learning by creating a blog and blogging on the things I am learning every day. I am also in the process of convincing a couple of other advisers to outsource some of their work to me. This will give me an chance to test and see if this could really work and with the results, I can convince my current boss.

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

    The 1st worst case scenario is that they dont offer me a full time role after my 6 months.

    The 2nd worst case scenario is they offer me a position but do not agree with the working remotely option.

    Either way, I think the next 6 months is going to be one hell of an adventure in starting the side project and working full time and making contacts through this new job and make my dream a reality.

    1. If you end up in Chile, let me know. I think we have some interesting brain pickings to do. What’s your blog?

  2. We’re all Phileas Foggs. Will you stay in your cosy London house or go for a little trip outside? Fill your life with new experiences now. I don’t see how you can regret it.

  3. Wow, so many comments here of people trying to figure out their ways in life & business.

    I think that instead of picking just one comment and help them why not propose this help under a paid service for all those people.

    I know that you time is limited but helping all the commenters here will benefit everybody.

    After all this blog is all about giving hope and different view office and business.

    I usually read only this blog because it gives the real deal for the readers.

    I will be happy to pay for the service the post authors offered for just one person, please think about it for the sake of all.


    Sam Goldfarb

  4. Hi. I am that staff editor at an Australian newspaper. Print is dying rapidly. My risk is to move into digital within the company, an area that is yet to make any money, and use it to springboard into the humanitarian aid field, an area that would pay less money, yet which I am passionate about.

    The risk is maintaining an income and work hours to support my three-year-old daughter and my new mortgage (acquired in a falling housing market). The greater risk is not acting – redundancies are expected to be announced on Monday.

  5. Hi,

    Tim: Thanks for continuing to inspire and bring great advise to us. Keep up the great work, my friend.

    Ben and Reid: Thanks for a wonderful message. Here’s my story –

    I am a 26 year old guy. I came to the US in 2006 to complete my BS in Aerospace Engineering and then went on to get my MBA. I felt that I was on the right path. An MBA in my hand? I felt almost invincible. I couldn’t be more wrong.

    Cut to 2012 – I have been searching for a job for about 4 months now. I am an international student in the US so, any company that hires me will have to sponsor my H1B visa. If I don’t find a job by August, I get kicked out of the country. I do not know if it is my qualifications, the economy or my international status that is hindering my job prospects, but I know that I will not let it take me down.

    Last month, I felt helpless. I almost felt betrayed by the USA, which I have called home for the last 6 years. I felt that I was robbed of my “American Dream” and the least the government could do was give me a permanent residency (like almost all other countries – Canada, Australia, NZ, etc) and not just kick me out of the country in August after such a long romance.

    However through all this crisis, I developed a sense of adventure. I questioned my ambitions. I asked myself, “Is this the only way to accomplish my dreams and career ambitions? Is this the only country?”. I was not raised ‘normally’. I traveled a lot as a kid, I have lived and studied in over 5 countries and my graduate school was my 12th school overall. Knowing my not-so-normal background, I was stunned at my persistence, now, to lead a very normal life. I wanted what everyone out there wanted. I was, as Tim says, eager to choose unhappiness over uncertainty. And that was unacceptable.

    So, last month I applied to English Opens Doors program in Chile. It is an initiative to volunteer as an English Teacher. I was shocked when I read about you too spending 9-months in Chile – if there’s such a thing as a sign from above then there it is! I was accepted into the program yesterday and I plan to move to Chile next month and teach English there for 6 months. At the end of the program, I plan to apply for Start-Up Chile ’13. I had applied last year but got rejected for not having enough ties and network in Chile. Now, after volunteering and connecting there for 6 months, I sure don’t think that would be a problem.

    Also, I have already got a job offer in Chile (after the volunteer work) as a language consultant for a startup company that was recently selected for StartUp Chile. I, unknowingly, made a friend with the CEO while Couchsurfing for a place to crash at when I land in Santiago next month. Now she offered me a job after a Skype interview, has promised to introduce me to some of her entrepreneur friends in Santiago and some mentoring.

    I feel the risk of leaving a sure-thing in the US and heading into the uncertainty has definitely been the right move. I haven’t even step on the plane yet and opportunities are already coming my way. It’s a small risk at the moment and my biggest concern is deferring my student-loan payments, but I know this is a once in a lifetime opportunity. If it works out, then I’ll have an interesting story to tell. If it doesn’t, then I’ll still have an interesting story to tell about my adventures in Chile. So, when I read this article I could very much relate to it and had to reach out.

    It would be nice to win this contest and get to chat and gain some important insights from you, but at the moment, I am just happy to share my story with the world.



  6. A big “thank you” to all three of you for this post and for the inspiration and comfort you ‘ve given me. I live in Greece, a country that up until (very) recently valued the stability of a “secure” (see: civil servant) career most than anything -and now is looking in disbelief as thousands of jobs are lost everyday and stability (in all senses) becomes an obsolete word. I will print out this post and read it again and again as I go about building my business, without knowing if my back-up job will be there for me tomorrow or if I will need to work in a field that I have never contemplated, in order to provide for my family and/or learn new things and stay on top of this game. I will share it too -because there are millions out there, in this country, who need this kind of boost more than even before in their lives.

  7. Mate, this post couldn’t have come at a more important point in my life, helping me think that I am indeed sane in what I’m doing.

    It can be tough for people trying to take a leap when it seems the world is against them. A post like this can change all that, a massive kudos to you to planting the seed.

    Hey Ben, Tim, Reid and everyone else playing at home.

    I’m Chris, I’m a Melbourne based guy and have been working with the web since school and have dont nothing but. I’ve always had a burning desire to make something that will fundamentally change the way people [INSERT VERB HERE].

    The first IT job I had, I wanted so bad I lived in a friends shed in the middle of summer since my home town was 2 hours away and I couldn’t afford the rent near the office. An experience I look back on both with humility and pride.

    While working full time, on the side I created my first startup, twithawk, which had moderate success and got some good attention in the US, and it was enough to wet the appetite. It’s still running, and evolving, and was a playing factor in the decision to leave work to pursue working full time on my own startup.

    The last 6 months has been all about risk, and so are the next few.

    I’m currently bootstrapping, but with the fallback knowledge that this experience in attempting to turn an industry on its head (an industry that 6 months ago I had zero knowledge about), has been the biggest growth of my career, and will give me the upper hand should this not work out and I need to find work.

    Added to that, the risks actually bring with them excitement, and as scary as it can be at times, it’s something I’d easily recommend, but do yourself a favour and build yourself up in risk levels rather than biting off too much too early, or you might scare yourself away from taking risks.

    For me, the next couple of months will involve pivoting a website that I just took over, changing it’s direction and and turning into a company. It’s my entire focus, and it’s completely new to me. I’m a web developer, not a CEO, not a marketer, but I’m going to go balls deep and give it a red hot go.

    I’m only 6 months into a 3 year payment plan which scares the crap out of me, but the potential upside has changed from my initial goal of financial independence to actually having a long lasting and nationwide effect on an entire industry.

    That excites me enough to take on the risk of potentially putting me into massive debt by ruining something yes contractually having to continue to pay off for another 30 months from now.

    Like I said before, I’m hoping that this experience will help me land a job should all fail, which over time will get me back into the black, but the thought of having a lasting effect on an entire industry is just too tasty not to chase.

    And all for an industry that my friends laugh at me for, a web developer trying to take on the hair and beauty industry, so not only am I risking my financial future, but putting up with the “hilarious” banter they come up with, it seems I’m in this alone, but the light at the end of the tunnel beckons.

    I wish the absolute best to everyone who’s left a comment, there’s some super inspiring stories in there. Too many to feel I have a chance at securing the invaluable prize, but it was something I simply had to chance at.

    Also, as an FYI, last year I created an app that does exactly what Alex Kourkoulas’s idea was to win the last competition, letting people use their own photo and add meme-like text and share with their friends. It’s called memefy, in the app store.

    For those that spared the time to read, thanks. Ben, Reid, Tim… good luck in finding a standout

  8. Thank you first and foremost for this opportunity to be able to spend a little time with the both of you. It will truly be an exceptional learning experience.

    I am currently working as a full-time police officer and to make ends meet, I work a lot of off-duty jobs. My wife is a stay-a-at-home mom for our one daughter, which I wouldn’t change for anything in the world. The benefits my daughter receives from having my wife with her far exceed any paying job my wife could have. In the next 30-60 days, I would like to take the risk of not working the off-duty jobs so that I may laser-focus my attention on what I would love to get more involved with which is product licensing.

    In February of 2013, I’ll be fully vested with my department, which means that starting at age 50, I’ll be able to draw the minimal amount from my pension or I could draw my full pension if I stayed another 15 years. No thank you! Being a police officer wears on you in unimaginable ways. A police officer, on the average, lives just five years after he or she retires. Not me! I have so much more to offer my family, my friends, and the world. There is way too much to do and way too much to see to be checking out that soon.

    The risks that I am evaluating affect my whole family as I am currently the sole money provider. I’ve also discovered that the risks I’m willing to take are not the risks my wife is willing to take. She see’s I’m in a secure government job with a nice pension awaiting at the end of the rainbow like your article speaks about above. I see that pension getting converted to a 401k and me trying to choke out everyone above the rank of lieutenant!

    I admit I’m an adrenaline junky but now that I’m in my early 40’s I am shifting my attention from chasing bad guys to capturing wealth. I want to be able to give back and to be able to pay it forward. With great mentors available such as yourselves, Tim Ferriss and Stephen Key, I know these risks are worth taking. The risks I take everyday as a police officer are so much greater than a lot of financial risks associated with my early retirement. I think that I’m just familiar with those everyday risks and I’m trained to react accordingly.

    It’s time for me to get trained up on how to take the unfamiliar risks that are sure to propel myself, my family, and my friends forward.

    A sincere thank you for your time and I look forward to hearing from you soon.

    Ron Dixon

  9. The risk of not taking risk throughout a lifetime of working for others can result in soul drain. As I have grown in my career, I have become increasingly fatigued. I’m finally doing something about it. Thank you Tim, Ben, and Reid for the inspiration and support.

  10. Fascinating post. Very timely as the Guardian just published this:

    My thoughtful comment (2 mins):

    Last year I prototyped a property design and development concept after a couple of years’ research.

    Although I’m an engineer I was really scared about the prospect of purchasing property in today’s economic climate, the design and developing, finding and dealing with trades-people, materials and products suppliers, council officials and national legislation, the financial commitments, and the potential end results.

    So I kept researching to try find answers that would make the fear go away. That data doesn’t exist. My fear did reduce as I learnt an amazing amount about relevant industries, but it never disappeared.

    I realised fear would never go away, so I started. I purchased a property.

    I designed my ‘worst-case’ scenario to be something I was okay with, part of which required finding the most affordable, best deal I could find, which happened to be a 3-year-vacant bedsit that had been repossessed, with needles in the overgrown garden, wet rot and woodworm on the inside, and I told myself that if things didn’t work out then I would at least have a home.

    I was involved in every single aspect of the project, often physically doing/assisting the work with my own hands.

    I rarely socialised last year as if I wasn’t doing hard labour in the property I was researching products and materials or project managing in the evenings. Friends would ask how I was getting on. I’d always say ‘I’m still really scared but I’m making progress’. When they’d ask me how I knew what to do and how, I’d reply ‘All I can do is approach everything with a learning attitude and the willingness to improvise’.

    The project went well, actually hitting my ‘best-case’ scenario model, and I learnt so much that I’ve had professionals who worked on it asking me for advice!

    On reflection, I think I can summarise the approach which worked for me within this risky environment:

    “Always scared, always learning, always pushing forward, always designing an acceptable worst-case.”

    And I now realise, regardless of how things could have turned out in the end, I can always be proud of my approach.

    Simon Scott

  11. I want to surround myself with successful people, and put myself in an uncomfortable place in the short term to get there.

    I’m thinking this risk will involve networking more, on top of the work I’m doing, and potentially risk anything I need to in the short term to get there (health, money, security, etc). I think this opportunity is a start, but it’s also going to involve traveling more and spending concentrated time and effort to make it happen.

  12. I have already taken big risks in my career:

    – I gave up my 9-5 Marketing/Sales salaried job to move to Panama with two kids under 4yrs old… from the US and become a freelance commercial writer and consultant for my previous employer.

    – It’s Time to take the next step in my career: Harness Amazon, Kindle, iBooks and other eReader/online book stores to self publish children’s books that I wrote for my kids.

    Plans are being made now so a 60 day roll out is not unreasonable with the proper input by you guys.

    Thanks for reading.

    Jesse Lee

    1. …Also, I began creating iPhone apps with no experience about a year and half ago. Currently, 1/3 of my income now comes from Apple… This experience shows you that I have the ‘scrapper’ mentality to hustle, learn quickly and produce ideas that make money.

  13. I’ve read the book–twice–like you might do with a good movie so I could superimpose the truth that was revealed within more than once on my constantly evolving menagerie of thoughts.

    Here’s a thought: In North America we’re rich by any world standard. Many of us do not vie for fulfilling basic needs. Often a roadblock to taking a career risk is relative comfort. We rationalize why we shouldn’t take a risk because of worry about potentially losing our creature comforts if we did.

    Example: My brother and I are both 8th grade teachers. He’s in public education (traditional). I’m in private education (Montessori). He’s feeling the dissatisfaction that comes with toiling in what amounts to a basically top-down management operation that restricts much of anyone’s creativity. He makes 40K more than I do and I’ve been in education two years longer than he has…I still wouldn’t trade with him. I get up every day (okay, more like 80% of the time) and say: “Great, another day where I get to go ‘play’ and get paid for it.” He’s not feeling that way. He’d like to take a career risk. He’d like to switch careers and become a personal trainer. He’s fit, in the gym religiously, a bachelor…he’s set UP to make this switch–and do it easily. But I’m 95% sure that he won’t. Why?

    He’s plagued by the potential ‘loss’ or ‘risking’ of his creature comforts. He fears not being able to pay his mortgage. He fears not making enough money compared to the 90+K he makes now (yes, he’s a teacher…I know!) which in turn, inspires fear that he won’t be able to feed himself, that he’ll struggle, that it won’t be as EASY as it is now, that he’ll lose what little autonomy his salary DOES grant him outside of his job.

    So, I guess my observation is that what holds us back is fear (duh) BUT, if we didn’t have it so good in North America…if we had less to lose by taking risk, there might be more people willing to take them.

  14. Dear Ben and Reid,

    I have taken significant risks in the past: Left a 10-year career with a large multi-national for the opportunity to grow a newer category with a smaller, more aggressive company. Grew the category from $12 mil to $110 mil in three years and gave notice when I was not rewarded. Took the very big risk of accepting the counter offer. Was assigned a $460 mil category and am on target to grow it to $920 mil this year.

    However, now I am faced with a situation that most people tell me is fantastic and I am seeing as practically a death warrant.

    You see I was promoted to Director, and am being asked to sign a non-compete agreement. Most people are saying, “hey you’re now at the executive level in a multi-billion dollar international company. Congratulations! Enjoy it”. But my head is screaming things like, “sign the paper and seal you coffin”; “sign and resign yourself to a life of mediocrity”, and “don’t let them own your ideas.”

    Trouble is, the agreement would limit my ability to pursue entrepreneurial activities. I’ve just launched a website to market an ebook I’ve written (10-minute Guitar Chords: the fastest, easiest way to learn. Guaranteed.). A primary purpose of the ebook is to build a mailing list to be used to market a line of unique guitar accessories that are prototyped and production-ready.

    Yes, I’ve just been promoted and have increased my income 34% in three years. But I am not willing to sign up to be a wage slave for the rest of my life. It is far too risky.

    Surely you, like me, know it is far safer in the long run to downshift on the corporate career track, and put the pedal down on the entrepreneurial circuit.

    Looking forward to having you select me for the 30-minute phone call with you. I have read The Start Up of You and 4 Hour Workweek more than once, and am striving to continuously improve my implementation of the principles (over 800 LinkedIn contacts, selectively growing and nurturing them). Clearly you can see I take action and get excellent results. After you spend 30 minutes with me, you will feel it was well worth your time.

    Thanks for the opportunity.

  15. Hi Ben and Reid,

    Wow. It is never too late to try again. After over 30 years in finance, accounting and technology, here I go again. Now involved in marketing Cloud hosting technology in Canada.

    I have dealt with working in the U.S and Canada, 4 children, two marriages and two strokes and still kicking. (health is much better now).

    I believe that you are never too old to keep learning and we are on the brink of another technological explosion.

    Any advice and direction you both can provide would be truly appreciated.

    Enjoy the weekend.


  16. Forget about Ben Casnocha, Reid Hoffman. or Tim Ferriss.(stickiness established)

    I know a lot of people have put up their ideas, dreams, and life story (some in great detail) on this blog for the contest. This is good. But as participants we have to consider the 99% certain possibility that you will not win. A contest is a sensation generating tool to create certain effects for the contest holder’s benefit, after all. So Let’s forget Ben Casnocha, Reid Hoffman, the contest and even Tim Ferriss. Yeah, Tim Ferriss is a cool guy, but he can’t help you with your idea/muse/project/career decisions. It won’t happen.(99.5% sure) Since you are the one taking risk and only one who can help yourself, it’s time to brainstorm what your next move is if you don’t win this contest.

    1. This is exactly what I meant to provoke with my own comments : a real risk of accepting this contest’s challenge is that of exposing, albeit thoughtfully, our career insecurities and wishfully thinking that a free book and an interview will resolve things for us.

      And the risk to the ones offering the reward, well, will be how the participants – winner and all the losers – choose to view them from now on.

      I’m willing to bet, though, that many of us have already been rewarded by the spurt of inspiration and moments of self-reflection needed to just participate. But you’re right, this is only where the fun really begins.

      1. Thank you , Tom, for reading my comment. Not many people read comments at all. It’s especially difficult when there is a contest which results in numerous and very long comments.

        I sort of like this contest. Put your name in a hat and you might win something. Sure why not? If people don’t put more emphasis than that, there won’t be any miscommunication or a mismatch in expectations.

        I strongly recommend caution when inspiration seems to hit you. This is because inspiration is usually fabricated and it is not real. Inspiring people isn’t really that hard because, through storytelling, it is the audience who is inspiring themselves. And let’s face it, people get inspired by almost anything.

        When we see a video, hear a pod cast, or read blog posts, we think that we are in the inner circle and given secrets of whatever topic. Of course, this is not true. Yes, we are here to listen to master storytellers, marketers, entrepreneurs and learn. But it is a very naive notion to think that those same storytellers, marketers, and entrepreneurs are not using those skills on us, the readers. Of course they are selling us, marketing us, and telling us stories with profit in mind. They get prestige, your email address(future marketing), your admiration and your money. You get to be inspired. Fair trade?

        So be careful.

  17. Some of the best advice I ever received was, “It doesn’t matter how much it costs to get into business with the right people. Just make it happen.”

    Those were the words of wisdom from my former boss when I was launching a new business in a market where I had just moved, didn’t know anybody, and had to succeed at a high level (or find another job). Eight months later, the business had grown to a headcount of 42 and was on its way to consistent profitability.

    How did that happen? I was focused on attracting the right people and helping them succeed. Everything else that went into building that business was a distant second place in my mind. Until I had built an amazing team, nothing else mattered.

    This is coming from a guy who took a 75% pay cut (!) last month in order to get into business with the right people, in an industry where I have to start at the beginning. I’m 33 years old and currently making less than I was making as a new college graduate 11 years ago. Why? Because I took an entry-level job at an exciting tech startup. And I did it with my eyes wide open.

    I don’t know where this job will lead, but I DO know I’m making new connections, learning new things, and exposing myself to ways of thinking that didn’t exist in my world before working there. How could I put a dollar amount on that kind of exposure? The distance between where I am now and where I want to go is a matter of relationships, and I’m willing to do whatever it takes to get the right people into my life. The short-term discomfort is insignificant when you consider the long-term potential.

    In the next 30-60 days, I plan to move into a larger role at my current company. The beauty of working with startups is you can often carve your own niche if your plan fits with the company’s vision. The risk I see is in approaching that conversation with the CEO. If my plan doesn’t fit with his vision for the future of the company, it could create an awkward situation or lead to my termination. It’s a necessary risk, but a risk nonetheless.

  18. Back in 2006 I was a common, manual labor construction worker. In 2007 I realized bosses/jobs will never get me what I truly wanted (money and time) and limited my creativity. I got a great PLOC, quit my job, started my own woodworking company and gambled way too much borrowed money into an investment that eventually failed. I plugged away with self-employment blindly. I educated myself by reading a lot, taking an Entrepreneur/Business course, networking and learned as I went. First hand, I realized that my self-employment was really just another job (actually jobs plural, that paid bad).

    I also have been dabbling with E-commerce/ Internet business, as I know this is the future.

    To keep afloat financially, I’ve worked a couple jobs since. But, I haven’t looked at the “wage” only. For the 17 months I have been working in Sales and learning more business and marketing techniques. Although, They’re nothing to write home about yet, I’ve created a Personal Brand/Blog, have joined a Toastmasters Club to become a better speaker and communicator. In my spare time (after family), I continue to keep stepping forward, outside my comfort zone, watching and waiting for an opportunity that will pay off.

    My real setback was risking a significant amount of cash and losing it. Though, I’ve had a tough time financially (barely keeping ownership of our house) for the last 3 years, the last words of Steve McQueen as “Papillon” ring in my ears…

    “Hey, you Bastards! I’m still here.”

    Thanks for the great post.

    Clint Moar

  19. I think the past few years has taught Americans and the entire world a lesson in that there is no such thing as safety and security when it comes to your job. Taking smart risks is essential in today’s world because you learn to adapt and handle things that come your way. Unfortunately, there have been so many displaced workers with jobs that could be outsourced and done cheaper elsewhere. Nowadays, the world is becoming flatter and we must all figure out ways to adapt. Here are some ways to acquire new skills:

    Start a business! Put yourself in an uncomfortable situation, but take smart risks. Start a business on the side but maintain your day job until you can afford to cut loose. Oh yeah, and do something you’re passionate about.

    Move to a foreign country! If you’ve always wanted to go abroad but never had the guts to do it, now is the time! Find a way to volunteer or teach English and build skills while you’re enjoying yourself in a foreign land.

    Take classes! We live in an exciting time where we have access to so much information at little or no cost. I always regretted not learning better computing skills. Guess what? Now I can take programming classes taught by the best in the country for free online.

    We only have one life to live, may as well go out and live it to the fullest. No one wants to live their life as a cubicle slave. Do what you love, take chances, and life will reward you.

  20. There’s going to be a career change coming my way. I’m not sure when, but I know there are huge risks involved. I’d be leaving a secure job where the top of the food chain is in my reach within the next year. My new venture leaves me a freelance writer, scouring the global stage for business and environmental capstones and conflict.

    There are plenty of risks, however only one can provide unlimited payoff.

    Current Risks- Staying in a career where learning opportunities are limited, and seclusion is the norm. While it comes with high pay and plenty of time off, the day to day tasks don’t ignite passion or play to my strengths.

    Future Risks- Embarking on a volatile freelance writing career. Meeting sources internationally and in fields where I have no prior contacts. Language barriers. Low Pay. Fierce competition on a local and global level.

    The Pay Off- Having an international network that spans several industries. Adventure of a life time. Using my strengths and passion to be a contender in a difficult vocation. Unparalleled learning opportunities. Overall growth.

    The true risk is never being able to live the life you desire and settling for mediocrity.

    Establishing myself on the local level will be a tangible success and will keep me inspired. Risking multiple trips a year to cover interesting opportunities will keep me focused on the outcome I desire and give me experience and connections where I need it most.

    I’ll be covering local entrepreneurs to start, joining a local entrepreneur club to network. I’ll seek international stories which affect local life. And I’ll seek to bridge the gap between what is possible here, and what may seem impossible.

    Time to use Tim’s language posts to get my Portuguese down, and I’ll be planning for a trip to Brazil this year where I can further learn the language and report on the business sector.

  21. I love this idea. Thank you so much for allowing me to explore my thoughts and feelings on such an impressive platform.

    For me, I have spent the last 11 years focusing on growing micro and small business. It has been very rewarding but my true, generally undisclosed passion since 1983 has been to understand life and our relationship as human beings to this experience.

    So in the next 30 to 60 days, I’d like to redefine myself and be seen more as someone who makes the contribution of empowering the consciousness of people vs. being yet another business growth agent.

    I’m bored, the market is bored and people are so overwhelmed with the business growth conversation they’re numb, along with being bored.

    As far as how I’m thinking about the risk, honestly, I’m scared sh_ _less. How do I make a living empowering others through the direction and re-direction of their human subtle energy (the BIG reason why I haven’t lived my true passion in life, leaning instead to the path I’ve always followed for making money).

    But, historically, emotionally, physically, spiritually and energetically, the time is here to make a move like this. The question is, will I have the courage to go from comfort of familiar to the realm of the unknown. What will that look like and how can I make it all happen now?!

    Big questions, big vision, big fears … but with discomfort comes powerful growth.

    Thank you for allowing me the space to send this out there in such a meaningful way.

  22. I am embarking on a complete life change as of TODAY. I actually just put my two weeks in at an Ad Network company in Los Angeles and had my last hard day of work yesterday! I quit my extremely stable, decently-paying job as a Product Manager with a rockin start up company so that I can head to Costa Rica for a month, earn my Yoga Teaching Certification, come back and get my Nutrition Certification- to open a health and wellness counseling business. I am planning on incorporating what I learned in my last job and in my yoga nutrition and diet training, to run a business that works by training and coaching individual clients and small groups, particularly in the corporate arena, on the topics of physical mental and nutritional health. Many of these clients are people who work hard, play hard, and also do some major damage on their bodies (I should know, I have been experiencing it firsthand). And beyond that, so many of these young hustlers are dying for a bit of balance. Because of my connections, I am hoping to build up a clientele shortly after I get back, but saving up enough money to actually open my own business location (complete with yoga studio, office and conference area) will be a LONG and difficult path. I not only hope to build a clientele amongst many of these blue, white or no-collar workers, but also want to open a kids summer yoga and wellness camp and teaching center, in which I would teach children and teens the factors of maintaining a healthy body and mind, meditation practices, and insightful food choices. My ultimate goal with this endeavor is to build a team of health and wellness experts and yoga instructors underneath me, run a studio center, and build out a lifestyle model that would be accessible to many who do not have an opportunity to spend tons of money on health coaches or personal trainers. I live in Santa Monica, CA and while this demographic is very tuned in to a more health conscious way of living, there are too many cities and regions that have absolutely no knowledge on this style of living. I have concerns for the future of children- who will soon be coping with high obesity rates, the issues of heart problems and cardiovascular diseases as a result of stress, and the impact that over-working has on one’s health. Hopefully I can be a part of the influence on America in making smarter health decisions and learning how to nurture your body. Unfortunately the path to opening a business as far spread and stacked with resources as the one I mentioned above will take some major time and savings. I would like to write my own books, do a road show and visit schools and businesses in order to reach a wider audience. Ben, I hope I hear from you, I have truly just risked it ALL to embark on this path because I feel like it is not only a risk, but a DESTINY that I need to fulfill. Thanks for your contest, and your interest in helping others make it happen. Appreciate your blog!

  23. Hi everyone, it always feels great when i read about how other people made it and became big entrepreneurs no matter what are the challenges!

    I am Moad from Libya, 26 years old, i did electronic commerce bachelor degree and worked in more than 10 different types of jobs on the past 8 years of my life, currently i work as an exams assistant at the British Council teaching centre, i learned English with a pen and a paper at my house then i went to learn Italian, i have learned self development materials throughout legendary masters such as; Jim Rohn, Brian Tracy and Zig Ziglar, i chased all start up companies and read about their experiences, now when this may sound just normal for many of you it is actually unusual to happen where i live, in Libya! i learned web development and now i set up my own website which i look forward to engage every single retail to start selling on it just like what happens on Ebay and Amazon! i think in a county where houses do not have address and delivery service companies are hard to find its a big challenge to even think about starting an ecommerce site. today i am only two weeks away from lunching the site on the internet and i can promise everyone in here that will be the next Amazone in north Africa.

    Moad Rgeyi.

  24. Hi,

    I’m John O’Leary and I am the only Mexican O’Leary you’ll ever meet (most likely). First, thank you Tim for all the years of inspiration. Your work really means a lot to me, and, especially, your willingness to share so many of your failures, since most don’t. Also, thank you Ben and Reid for being so kind to share your time and insight.

    Here is my post to be considered for the competition (under 500 words):

    It’s a beautiful city full of warmth and culture in the eastern arm of Mexico. It’s Merida, Yucatan, Mexico, and I was born there. My parents are both scientist-artists, so education is very important to them. My father is an American photographer-anthropologist, which of course explains why I have a very not-Mexican name. And my mother is a Mexican concert pianist with an MD.

    When they split up for good my mother had this giant dream and took what seemed like a giant risk at the time. We decided to leave everything we had, our family, and friends to move to this great country. She was smart, and turned our dream into a 3-month summer experiment. The goal was to get a job, and find a community of support. If she failed, we would come back at the end of the summer and resume like normal. But if she succeeded we would have a chance to pursue the American dream, and for her (and my dad) that meant that I could have an American education.

    She succeeded! I am finishing my PhD in the neurobiology of stress (serendipitously with this post it’s on resilience, and how it can help prevent and treat stress-induced psychiatric diseases). And my mother has had a wonderful career inspiring children as a spanish, music and biology teacher.

    Now, it’s time for me to pursue my dream. I want to be an entrepreneur, and a professional jazz pianist, and find a way to incorporate science into them. I already play jazz piano professionally in my area, and so the change that I want to make in the next 60 days is to start my first business. This is something that I have been very passionate about for the past 3 years since I first read Tim’s 4-Hour Workweek, but I have failed to put something for sale, over and over. Every time I tried to start I found a way to “overestimate threats, and underestimate opportunity and resources,” and quit.

    Except this time it’s personal! Thanks to this post (thank you Tim, Ben and Reid!), and to the desperation induced by three years of complete failure, I think about risk differently: I take little bets (like this one), I purposely try to stick out in little ways to help me deal with the fear of public ridicule and criticism (like driving the speed limit, and quitting a perfectly good and safe career in science), and I consciously manage my anxiety by meditating on overestimating myself and the opportunity, and on underestimating the risks, since I am very gifted at doing the opposite! Also, I realize that the reason my mother succeeded was because she tried. She performed the experiment.

    I have 1-2 years left in graduate school, and the same amount of time to make a living from music and business. This is my experiment and I believe in it! Thank you for your time.



  25. Hello all, my name is Brendan Ronan. I’m a motivated, passionate renaissance dude with a primary career goal of traveling and exploring the world while working remotely. In the past 6 months, i’ve begun the process of self actualization (left my worthless and stifling retail job, re-tooled my skill set and working tirelessly to found a legitimate and interesting tech education business) and am laying the groundwork for a new life.

    In the last 90 days, i finally left a job that was highly time intensive, highly stressful, and thankless (think: TPS reports from Office Space), and have found a legitimate employment working 3 days a week as an entry level Web Developer (My qualifications? A few online classes taken for free at the local JC). One paycheck pays the bills, a luxury which has lowered my stress level and provided me legitimate time off to be productive at home, and the best part is i’m ingesting truckloads of information daily. In the next 30 days, i hope to have a venue secured for my business concept and in the next 60 days i intend to be marketing our first session to the world. At the time of this writing, i have no idea how to do either.

    I have worked extremely hard to minimize my risk in this situation, but i am also an amateur with no prior experience. At times i feel as if i’m shouldering too much of a burden; Other times i wonder if i’m aiming high enough. I guess these are the kind of questions an ambitious 26 year old asks himself when he’s fighting in the trenches to create a better life.

  26. I had an opportunity to start a company with a friend, but it was in a foreign country. He was going to do it with our without me, so it was simply a matter of if I was going to be a part of the experience. I had a nice management position at an aerospace company making good pay, so I had quite a tough decision to make! But not really. When I looked at the situation critically, I saw that I had but one option. There were four possible general outcomes–four futures:

    A. Don’t go and they fail (whew–missed a bullet!).

    B. Don’t go and they strike it rich (bummer).

    C. Go and we fail (another bummer).

    D. Go and WE strike it rich (Yeah!!).

    In option A, although I might feel vindicated in my “wise” decision, I would be constantly plagued that things might have been different with me pulling my weight–some possible (probable) regret. In option B, there would be much regret for having missed out on the opportunity. In option C, at least I would know that we went down fighting and doing the best we could–who knows? It might even be fun regardless. Option D, of course, is the desired outcome.

    Given that one of these scenarios was the inevitable futures, I saw that I really had no self-respecting choice but to go. I now live and work at the company in Medellin, Colombia. How did it turn out? Well, it’s still in process (2 years now). But I have absolutely not regrets and it has been (and continues to be) a blast.

    If I had focused on ANY of the risks, I would not be here today. The risks (and there were many from severed income to foreign-country issues) clearly would have overwhelmed any “cost/benefit analysis” I could have done. Instead, I focused on the outcomes–on the POSSIBILITIES–not on the risks nor on the opportunities, and saw I really had but one thing to do if I was to be at peace with myself thereafter–I had to go for it!

  27. I was born and raised in a small town in Azerbaijan (you may not have heard of the country). At the time when I was graduation from high school I knew I wanted to be different from everyone else who surrounded me, I knew I wanted to do something extraordinary but I was not sure how to get there.

    Not knowing much about the rest of the world or the opportunities available (well, there was no internet in my town until after I graduated from high school) I headed to Turkey to work on my English language skills and to see more of the world.

    It was here that I learned that there was such place called MIT and one can apply and get full scholarship. I decided give it a try and managed to get in the top 3% of MIT undergrad applicants who were offered admissions. Who knew?

    When I was graduating in 2009 it happened to be difficult time to look for a job especially if you were an international student on student visa requiring H1-B sponsorship and otherwise had to leave the US. The economy was not doing well at all and companies were going out of business.

    Nonetheless, I decided to go for a startup called AdMob (turning down my two other offers) because that is what I wanted to do, a startup. It turned out to be a really good move – AdMob was really awesome place to grow and we were later acquired by Google. After almost 2 years at Google (and getting my green card) I am out to start a company of my own. Now, I imagine the next 30 days are going to be amazingly adventurous and I will do amazing things.

    I believe risk is a way of life. It is the way you think, the way you breathe, the way you talk, it is the way you live. I have learned this throughout my life and this thinking has not let me down.

  28. I thought for a while about this and came to the conclusion that I’m not sure how you could help change my career in 30-60 days. But it’s free so what the hell.

    I’ve felt stuck in the same job now for almost 6 years. I tell myself I hate it and want to get out, but have never followed through. After I read 4HWW I decided I needed a job I could do remotely (I’m a meat cutter/manager). For some reason I clung to programming with the idea that I could practice by making a website for my boss for free. I completed a free tutorial on html online, but never made the website.

    That was a year or two ago. Now I’m feeling the itch again. I recently read Jane Goodall’s In the Shadow of Man. I was blown away by the observations she was able to make studying chimpanzees in the wild. And I was drawn to the idea of roughing it out in the wilderness, carrying everything you need on your back, watching animals in their natural habitat. It’s become my dream job. But I have no idea how to go about getting a job like this. I contacted the Jane Goodall Institute, but never heard back. So I thought I might get a job as a zookeeper to get some experience. I applied to a couple places already knowing that I’m underqualified for the most basic entry level position. Apparently you need a B.A. to shovel shit. So I decided to volunteer at my local zoo. I’ve only had an interview so far, but was pleased to hear that a volunteer went on to study animals in the African wild on a temporary basis. Being seasonally employed to safari in Africa is a risk I would definitely take.

    The risk in volunteering is minimal. I lose a little free time I would’ve otherwise wasted with distractions that kept me from doing something about my discontent. I don’t have a lot to risk right now, because I’m already poor. Not foodstamps poor, but free health insurance poor. I don’t even own a car (I’m not complaining, I actually like not buying gas.) But the one risk that I have been dodging is going back to school. I only have about 15 credits left for a B.A. in psychology. I finally got all my loans paid off and the idea of accruing more is not appealing. Maybe if my degree was in biology, or something related to zoology, it would be of use. I don’t know if my grades would be good enough for a Masters program. And I don’t know what I can do with a BA in psych, except be a counselor, and that isn’t appealing either.

    Then I had the idea of going to a 2 year technical school to learn programming so I could do contract work in my free time. I still would like to achieve the level of freedom that 4HWW outlined, but I’m not sure if I can divide my time between two new ventures and still work full time.

    But I have to do something, because the biggest risk I face is doing nothing and staying in the same job for the rest of my life.


  29. I think one thing I would like to do is quit all together. Focus on starting something that I love and have it work for me. Use the increased free time and flexibility to travel the globe and work from anywhere in the world.

    I would love to have a portion of my sales go to charities as well and free myself to travel globally helping various people in a multitude of nations do whatever it may be that they struggle to do daily that people aren’t aware of here.

    Being rich isn’t my goal. Being free to experience this life and help others do the same is. A goal of escape.

    More specifically a startup I’m trying to initiate is in regards to shipping monthly boxes of healthy food to people, of which a small percentage goes directly to feeding people in need.

    Thanks for such an inspiring and enlightening post!

  30. Well I have been involved in contract/freelance programming works for some time now giving up the temptations of full-time, high paying job in IT companies. I intend to excel in this kind of work. I need motivations, mentoring to prosper.

  31. After Living the spontaneous life for three months across Europe, studying full-time and working part-time didn’t give me the fast-paced run I craved for. I wanted challenges and I wanted them now.

    After working part-time for 2.5 years in the current company I was working in, I applied for a leadership position.The catch? It meant I had to work full time, and I was studying full time. Furthermore, the day I got the job was the day they announced that they will be looking to offshore that department overseas and testing would be taking place.

    I used Tim’s approach, “What’s the worst that could happen?”

    The risk:

    – Failing subjects at Uni ( AKA- College) due to pressure to work both roles.

    – I was entering a role that could not offer job security in the long run, this meant I could lose my job.

    The opportunities:

    – I have obtained a leadership role within a major bank at the age of 21.

    – I have great examples for interviews for change management/environments.

    – I have the freedom to create my own challenges, push myself to another level from both a personal and professional perspective.


    Taking that risk actually allowed me to perform better in my full-time studies at Uni. I had no time to procrastinate, and I achieved the best results since I started my Commerce degree. It improved my time-management skills and I still had time to have a life!

    I gained experience in mentoring, public speaking, reporting and analysing data, presenting in front of upper management and I built many relationships in the company.In less than a year of being a Senior Associate, I have gained more experience than I would have ever gotten working part-time and procrastinating at Uni.

    I applied for another Senior Associate role, which is eventually being sent abroad overseas as well. However, once again the benefits outweigh the costs. The experience I’ve gained by the time I’m 23 will hopefully put me ahead when applying for graduate roles in investment banking industry. Which will present me with my next challenge – Quitting my job to obtain a lower income, internship role.

    “What’s the worst that could happen?” is one line I live by when weighing up the risk vs. opportunities in any aspect of life because when you actually say the risks out loud compared to the opportunities, it isn’t as bad as you think!

  32. I think the post does a good job re-defining the word risk as a feeling inside of us. I think the biggest message to get out of this is that it’s GOOD to be uncomfortable and become accustomed to hustling in life a little bit. I felt I could really relate to the post because I recently quit my job. I decided I couldn’t keep working like a slave and I finally slapped myself for saying ‘should’. I’ll never say the word ‘should’ again – it instantly disqualifies most the opportunity I have at the moment. You either do it or you PLAN and DEFINE How, Where, When, and with who you’re going to do it.

    I don’t know what it is about us but I think our lazy tendencies mixed with our ‘I can predict the future’ powers tossed in with our ‘I wonder what they’ll think of me’ function makes us our own fun police – and my work was simply not fun.

    Be true to yourself and ask yourself whether you’re actually doing what you want to be doing with your life. Think about all of the things you grew up wanting to do – have you experienced them? Don’t blame it on anyone else if you haven’t – blame it on your unwillingness to take risk. Then slap yourself and start taking some risks so you don’t have to do this again 5 years later when you realize that hoping something will happen won’t make it happen

  33. Hi, Chase Doran here.

    I own a company called WolfDisc LLC that sells the first ultimate discs with a rim grip.

    Sales on the field are going alright, but sales online are lacking. Selling exclusively at tournaments doesn’t scale very well as a student at the University of Florida trying to maintain a 4.0 GPA.

    To fix this and seize the next opportunity, I’m going to:

    -Take a play out of Tim’s book (turns out if you take his advice, its generally pretty good. Imagine that!) and start using actual metrics to differentiate my disc from other discs (turnovers per game, # of accurate tosses through a hoop 30ft away after 50 tries, etc).

    -Take a play out of Chase Jarvis’ book (also very good) and make sure to include on the site the story of what went into actually making the product that they will hold in their hands and give people an appreciation for it.

    Even further down the road, I’m planning on using video from the trials and research along with testimonials to create a really kick ass, well done video.

    The risks of losing money (and time) are great, and the company still may not achieve our goals. At the very least, I’ll have that much more knowledge of how to run a successful company.

    I figure that if I can fail faster, then I’ll learn faster, and be where I want to be with a company I’ve created at some point in the near future.

    Thanks for your time and the great read!

  34. Wow, that is a ton of comments – how to stand out…?


    Great post. I think it’s important supplement this message to make sure people dont go risk-overboard and miss the underlying point: to make better and more fruitful decisions.

    The point of the article is to recognize the brain’s natural tendency to over value the downside of risk and assign it more weight in the decision making process. The article urges you identify this shortcoming and recalibrate your decision making algorithm based on this knowledge – it DOES NOT give you a free pass to choose the riskiest option available in the decision set and claim that Ben and Reid said its OK.

    The ultimate goal of understanding true risk is to be able to make the optimal decision – Ben and Reid have illuminated the path to true risk, it is still up to you to decide what the best decision is now that you have a more clear view of the variables.


    As a background, I’m a risk taker. In Feb of 2012 my wife and I quit our stable, high paying jobs (me as a software solution account exec for local governments and my wife as a public finance attorney working for a firm in Chicago) to travel the world. We’re currently in Panama about to sail across the Darien Gap to Colombia. I started my first company in late 2011 and broke the $1M mark in revenue the first year giving us enough cash to do some geo-arbitrage per Tim’s preachings.


    I have always wanted to be an entrepreneur, but until my recent success, I was a wantrapreneur (to use an AppSumo-ism). Now, following the success, I’m confident that I have the skillset and drive to make it happen again. The difficult choice came last week. Until last week I had been planning to travel for a year with my wife and come back in Feb 2013 and start my 2nd company. That decision became a bit harder when I was recruited on LinkedIn by an interesting technology startup. I’ve recently been given a great offer to work and learn from people much smarter then me, sharpen my selling skills, and work for a company who’s technology does global and social good.


    Identifying the riskier option is easy: go with uncertainty and start a company in 2013 and overlook the guaranteed paycheck. But this post isn’t about picking the riskiest option and disregarding all other criteria – that would be a pretty awful career heuristic to follow. I want to make the best decision here, not the riskiest. Knowing which to pick is the difficult part. That is my ultimate question and the reason I could benefit greatly from the 30 min session. I’ll be listening to the audio book anyway (assuming its on Audible) so maybe that will point me in the right direction…

  35. Well, I’m two for two on working in non-volatile careers: I have been working in the education field in school boards and provincial (state) government for the past decade.

    However, that doesn’t mean that I’ve sat back and chilled out – I can’t.

    In an bureaucracy loaded with PhD and Masters program graduates, I can’t lay claim to an undergraduate degree – not even an associates degree. I have to work harder, be more creative and hustle more than my counterparts. I’m grateful for this.

    Now that I’ve worked in government for a little over three years, the blinding flash of the obvious has happened: government does not innovate and does not take risks. I finally realized this two months ago (I didn’t say that I was a fast learner – LOL!). I recognized that this is an environment that will drive me crazy.

    I’m not the type to sit around and moan about the politics, the lack of innovation, and the leadership issues. There are those who have been doing this for years.

    If I don’t like a situation, I try to change the conditions, and if that can’t happen, I change my situation.

    So…I’m packing my bags, moving to another city and taking up a position with the most innovative school board in the province. They are creating a job tailor-made for my skills, attributes, and interests.

    When I get there, I’ll need to plug into the community and start making connections. I’ll also need to learn the politics of the province’s largest school board and build relationships there very quickly. And in the meantime, I’ll need to handle a million details stemming from my old life.

    I don’t know what it would take to “win” this contest (such as it is). I do know that I can handle this change on my own. I also know that it would be easier to manage the change with a bit of advice.

    Thank you so much for the article. I’m planning to morph this into something to help school jurisdiction leaders think about accepting greater risk when it comes to innovation. We keep framing the issue rationally, but there’s an emotional frame that we’ve been missing…

  36. Hi!

    My name is Morgan. I’m a Canadian that’s always looking for my next adventure.

    I’ve started my career change a bit already. I had a stable 9-5 interactive development job that I left 3 months ago. I am now working as a nanny on a farm in the Northern Territory of Australia. I love to travel and experience other culture. The goal of quitting my job was to travel and start my own business. I want to become a travel blogger and entrepreneur. I’ve gotten some really positive feedback from people so I’m starting to think making a living at it is a real possibility.

    The biggest risk for me is not making enough money to pay my student loans ($1500/month). I make just enough with my nanny wage. I now make in a week what I used to make in a day. I’m surviving, but not having any income could be detrimental.

    Another risk is that I don’t have the connections that I need. I am in need of a great mentor. I feel like I have enough knowledge to do really well, but guidance from someone that’s already been there is essential.

    I’m not worried about landing on my feet. I always find a job when I want one. I’m keen, adaptable, and a fast learner.

    Thanks for the great post Tim!

    Kind regards,


  37. What have I risked? After 12 years of being a decorated public school teacher, I’ve had enough with fighting against this mediocre, socially-engineered school system and its guardians, and have decided to intentionally create the condition whereby I was laid off from my job last week- nine days after the birth of my daughter- so that I can devote this year to launching, marketing, and selling a new kind of vodka to a particular type of consumer. I’ve been discussing and planning with a contract distiller and bottler for the past 12 months and we have been working with the ttb on our formula; we expect formula approval in the next 30 days, then label approval 30 days after that, then our first batch will hopefully be bottled and ready for market about 30 days after that.

    As this vodka is intended for a particular audience that isn’t really being marketed to by spirits producers, I’m hoping the uniqueness of it will garner public/press attention and bring in positive initial sales, in order to afford continued production.

    I’m risking a hell of a lot here- potentially ruining my “safe” teaching career (which has quite a colorful backstory) has me teetering between terror and excitement. I have no working experience whatsoever in the spirits industry (though I’ve learned quite a bit over the past 12 months), which business philosophies like the E-Myth say can actually be a very good thing (yes, I’m holding on to whatever hope I can get here).

    I’m writing this at midnight with my wife and newborn sleeping right next to me, to say, I would absolutely, positively appreciate your help to make this thing work.

    Does this sound risky enough to you?


  38. Dear Tim

    another useful and interesting train of thought that I am sure will set many of your subscribers off on adventures in thoughts and deeds they might never have started had they not been exposed to it.

    Over the past few years I have given considerable thought to the issues raised by Messrs. Casnocha and Hoffman and on the premise of my having little to lose by trying, a year ago I left the US law firm in Hong Kong, where I was a partner and set up an “eat what you kill” firm with two like minded partners.

    For the past 32 years I have practised law in London and Hong Kong in what is arguably the most specialised legal field in existence – maritime casualties or as we call it “bumps and scrapes”

    for 3 decades this has been a challenging, interesting,remunerative and fun business which has taken me to ships and ports all over the world, sometimes at considerable personal risk. There are only a handful of lawyers doing this sort of work in the world and most of us are known either personally or by reputation, to one another. All in all, an enjoyable first career.

    However, shipping is an up and down business and the downs in the market tend to last longer than the ups. That has made me look out beyond my comfort horizon for other things I can do which can fill the gaps when casualties don’t happen (or I don’t get a piece of them).

    The legal market in Hong Kong is primarily divided between the large international firms servicing large multinational companies and local firms concentrating mainly on private client work. That leaves a yawning gap in the market for the fairly under-serviced Small & Medium Enterprises which are not targets of interest for either the local or international firms.

    The SME’s are not large enough to have in-house lawyers, cannot afford the fees charged by the big international firms and have needs that are not readily serviced by the local firms. They also require a degree of certainty in their overhead costs which is not usually available when instructing Hong Kong lawyers.

    To service this need, I have started offering a basic, general legal service at a fixed monthly subscription fee which is entirely transparent and enables my clients to have short telephone or email advice on matters that are concerning them, letters of demand to persons owing them money, responses to letters of demand addressed to them, review of contractual and transactional documents, employment advice etc.

    Having spent most of my career “fee earning”, I am a little short on the marketing skills I require to make this business fly. To this extent I am taking a risk in being able to attract the right kind of client but I am sure these skills will materialise as I get on with it.

    Thanks for making me aware of Ben and Reid’s book which I will try to get hold of this week.

    With kind regards

    Peter Mills

  39. I’m a 30 year old lawyer, and I just moved to China a few weeks ago for my wife’s job. The move required me to leave my job with a law firm in the US, so now I am essentially unemployed and looking for my next opportunity.

    In the next 30-60 days, I hope to start a new chapter in my career, one that may take me away from simply practicing law. I hope to use what I have learned in law school and legal practice to provide a fresh and valuable perspective in the business world in a new country. I am learning that making this transition may be difficult because lawyers typically only have (or think they only have) the skills and knowledge needed to act as lawyers. Convincing myself and others that I have the skills and experience to make significant contributions to a business will be the main challenge for the next few months.

    As for the risk, I have already made the big leap and have left the safety of regular employment. The primary risk I see right now is the risk of wasting time and resources. I am anxious to start something (anything, really) so that I don’t feel that I am wasting time, but I think I have to balance that desire to get started now with the need to make a good decision on where to focus my energy. I need to determine a direction and a focus for my learning and working, and I have to do that without knowing everything I would like about each of the myriad of options. I have an amazing opportunity to start fresh, an opportunity that may not come again, and I want to make the most of it.

    Ben and Reid, I would love to have your thoughts on where to go from here!

  40. I started Hunter & Bard a year ago. We’re an marketing and design agency located in Israel that works with start-ups, small companies and intrepreneurs. Our business model is taking a small bit of equity in addition to cash – and we only work with start-ups that we think will make it. One more thing – we’re all women from North America (American & Canadian).

    I took a risk 15 years ago moving to Israel. I took a risk a year ago opening the agency. Now I want to grow it and have several branches (Far East and SF to start). We have a good solid base here in Israel now. I mentor at The Founder Institute (in Israel), The Junction (local accelerator), Microsoft’s Accelerator, and have given lectures at several local colleges and universities in various entrepreneur programs. I want Hunter & Bard to grow internationally. To be THE marketing and design agency that start-ups use to grow. Having Ben and Reid as connections would be nothing short of amazing.

    Thank you for this opportunity,


  41. #1: In alignment with my goal of launching my own nutritional supplement company I want to work on a voluntary basis with one of the worlds leading companies in this field (Gaspari Nutrition) as they are a perfect role model and would be my version of Ben’s product design experience with Apple. I will contact them right now and get the wheels in motion.

    #2: There are multiple risks involved such as time management, conflict of interest as my retail nutrition store is a customer of this company among many other similar competitors, I live in Australia and this move may involve moving to the USA for a period of time (which I’m super keen to do anyway, I want to shop at Wholefoods!), all in all I love change, uncertainty and/or chaos and am determined to make this happen with or without Ben and Reid! (That being said, I’m meditating on winning this and look forward to the call and email session)

    Brilliant blog post!


    Christian Baker

  42. Dear Tim & Co,

    very great post, exactly what I am living up to so far.

    I have a background in strategy consulting and I am also writing thrillers for the German and European market. My latest thriller, Final Cut, about a serial killer who approaches his victims via the internet, made it into the German bestseller list.

    For a quick summary in English, have a look here:

    I am also advising companies on corporate storytelling, which is, how to tell the story of your company in a convincing and sticky way. As I know the world of business and storytelling, I am able to tell companies more than some guy, who just knows one of these worlds.

    While being successful of doing corporate storytelling consulting in Germany, I would like to take this to a global scale. I could imagine, companies in China would need a good story to more differentiate themselves as premium providers.

    For any advise, which risk to take to take this global, I would be very grateful.

    best wishes


  43. I quit my job to start my second company (I already started an automated niche lifestyle business as a learning experience). Realising that the success of a company is greatly tied to the strength of the team you surround yourself with, the mentors you have and the amount of energy you can devote to the project, I knew that quitting my 9-6 job was vital.

    But like most people with new business ideas, the requirement for income to satisfy the monthly bills often takes priority. So my business partner and I worked intensively for 10 days to establish and launch our startup that will fund our actual startup. We launched a creative agency and within the first 3 days had secured our first project which was plenty to sustain us both for a month. We set one rule for our ‘startup to fund our real startup.’ It couldn’t take up more than 2 days a week of our time. So within 10 days of quitting my job, I was earning more than I was in my full time job even though I was working only 25% of the time.

    With the income from this comes freedom of time to work on our real startup. I’ve always found Tim’s principle from 4HWW of “What’s the worst that can happen?” to be a great guide for life. Every great opportunity that life has presented to me has stemmed from an inherently ‘risky’ situation that pushes the realms of normal comfort.

    When you think about it, it’s not surprising really. Much like human muscles respond to increased stress by growing, we develop as people by placing ourselves in stressful situations of uncertainty and risk.

    If you think something is risky then there’s a great likelihood that the general population agrees with you. This presents a fantastic opportunity – less people will tackle that risk and there will be greater reward for the person who tackles and conquers it. Treat risks as opportunities and life becomes a lot more fun.

  44. I have one dream in this world: get paid to be me.

    I’m tired of being a cog in the gear of a large company that gives two shits about who I am; as long as I keep raking in the money. I want to be a part of something bigger than myself; which is why I write.

    I am diligently working to infuse a simple principle into my life: enjoy the journey. Not in a hedonistic fashion, but one of true and genuine appreciation for all that we currently have in our lives. I’ve found that one of the fastest ways to get somewhere you want to be is to appreciate where you already are.

    The catalyst for this life principle was a similar experience to yours in Chile (though mine was more along the lines of a travel experience than living). I sold everything I owned (literally on Craigslist), packed up a 40 pound backpack and bought a one-way ticket to London in 2010. Three months, 13 countries, and 28 European cities later I finally landed back in the U.S.

    My life changed forever.

    Ever since, I’ve been struggling to find my place, my purpose, my mission. Through much trial and error, highs and lows, and failures and triumphs I’m beginning to see the big picture. Like Santiago in The Alchemist, I’ve finally discovered my personal legend: share with the world what it means to enjoy the journey.

    If I had 30 to 60 days left to live I would stop at nothing to get my message out to as many people as possible. The blog I write,, would be known worldwide. Offers to publicly speak would be pouring in and my inbox (which I don’t like checking often) would be blowing up with questions, comments, and thoughts from all those who read my writing and listen to my speaking. Book deals would emerge and I would be one step closer to my goal of having a New York Times bestseller. I would no longer be working dead end jobs whose only purpose is to pay the bills while I pursue my dream. Now, I would be living my dream and working for myself.

    Is this impossible in 30-60 days? Not at all – but it’s definitely not easy. I’ve seen it happen to far less qualified individuals. The main difference between myself and the indiscriminate masses who stumble upon success: I’ve been preparing my entire life for this moment. It’s not arrogance, just confidence.

    So, what am I doing to make this happen? Constantly writing new content for my blog and doing my best to see that I do one thing each day that scares me (makes for great stories). I’m writing guest posts, making sincere comments on other blogs, and telling everyone I meet about my blog to increase exposure. I’m working on a free ebook for new email subscribers – a manifesto. I frequent Toastmasters and attend improv class to fine tune my speaking skills and feel comfortable in front of an audience. I know what has to be done, I just need to consistently do it. I’ll continue to do what I do – improving, growing, challenging myself – knowing that each small step I take will eventually culminate into something huge. But I am always looking for that big break; the homerun.

    There is one concern.

    I would be lying if I said I wasn’t scared shitless of being put in the spotlight. But the fear is a distant second to the excitement and shear joy I receive from being in front of an audience – whether they are reading my work or listening to me speak. The butterflies always subside, but the high I get from delivering a genuine, heartfelt message that I truly believe will help people enjoy their life is unforgettable.

    I want to get paid to be me. No more mindless time consuming jobs. I am going to be a respected author and speaker with the freedom I dream about… it’s only a matter of when.

    I want to sincerely thank you for taking the time to read this comment. Best of luck with your contest!

  45. Tim, Ben, and Reid,

    Thank you for the wonderful post and the continued inspiration you all bring to me on such a regular basis.

    I am a 32 year old investment professional working in Finance, Asset Management to be specific. I am in charge of identifying talent (such as Portfolio managers, analysts, and traders) and bringing them onto a platform where the firm invests its own/client capital. I’ve been in this role since graduating from college and currently have achieved a high amount of success at a relatively young age. I mention this with fear of sounding arrogant, but it factors into the challenges of objectively evaluating risks and opportunity costs, two points which I will address below.

    One of the challenges in being entrepreneurial in the finance industry is that often (but not always) one of the key traits of success is experience (i.e. age or “gray hairs”). If you compare it to the tech industry, a programmer could study/program intensively for, say 5 years, and take this experience to launch a new company. While this is definitely possible in Asset Management, that same individual would likely hear criticisms such as “haven’t invested through different cycles,” “haven’t had to make enough individual decisions,” or “strong performance can be attributed to good luck.” More on this point too.

    My ultimate goal is to build an incubator of investment talent, providing them with the infrastructure, relationships, advice, and capital to harness all of the collective talent and investment ideas. While this would initially start in securities, the concept could be expanded to include any form of investing including private equity, venture, real estate, etc.

    My 30-60 day goal is to introduce the concept to potential partners in a more direct manner with the ultimate goal of building something by next year. To achieve this goal I have used one element from your book, which involves strengthening my weak ties. I’ve made a commitment to spend the entire year meeting 3 new people a day (bkfast, lunch, and coffee/drinks/dinner) and testing the idea with them. I get to kill two birds with one stone, because as an identifier/evaluator of talent, this type of networking also helps lead me to the “raw materials” for my craft. After each meeting, I map out patterns, common threads, and of course, criticisms to my idea. I’ve been pretty disciplined in systematizing and logging all of the comments… (it has been hard, I work 12 hours a day as well!) I do feel that I am missing a key sounding board for a few reasons: finance-types tend to be less entrepreneurial, confidentiality concerns, and age constraints (my peer group seems to be right in family-starting mode). Given this void, I have tried to make the best of this opportunity to learn from Ben and Reid.

    How do I think about risk? This is interesting, because as an investor (in capital markets) it is a question we think about all the time. We think that we can understand and more importantly QUANTIFY risk, which has arguably lead us to the recent Global Credit Crisis and makes it harder for me to avoid the negativity bias you so clearly describe.

    Finance generally quantifies risk using the volatility metric, which is the typical movement of a stock over some pre-determined time period (if I were explaining the concept to a child, I would use the metaphor of waves in the ocean, with turbulent waters being higher volatility). All things being equal, if two stocks have the same projected return, an investor should pick the one with the highest volatility. Finally, the common (AND FLAWED) assumption is that stock returns are normally distributed, that is, have an equal chance of winning/losing.

    This is where your advice has really been key to the continued development of my concept. While I have to be honest with myself and my ideas, you have very well illustrated that the downside risk can be both OVERSTATED and CONTROLLED, which will help me to better frame the appropriate risk to take on the upside. You have also helped me see that upside is not just success of the venture but the EXPERIENCE gained in the process. I always hear that some of the best start up experiences were the ones that failed, and that should not be discounted in this calculation.

    The one area I wish your article would’ve spent more time is OPPORTUNITY COSTS and where I struggle personally. I see two primary opportunity costs: TIME and INCOME. As I mentioned above, my “day job” requires 10-12 hours a day so all the “building” takes place pre- and post- work. Furthermore, given my title, income, and desire to start a family soon, the direct opportunity costs become harder. This is a common struggle and I don’t think I am in any unique position relative to other aspiring entrepreneurs.

    Your post, particularly the advice on “defaulting to yes” assumes that one’s time is an infinite resource. In reality, it is our most scarce resource and it makes the process of sizing up the risk/reward math even more CRITICAL. I’ve gotten myself in trouble from saying yes too much (YES, I’ll read this article; YES, I’ll take on the consulting assignment, YES I’ll comment on this article). If you were to select my comment, understanding how you each deal with this would be one of my first questions to you.

    Finally, I wanted to touch on behavioral biases. Again, putting on my finance hat, the one bias we are always highly attuned to is Overconfidence. It’s interesting to contrast overconfidence (overplaying your strengths) versus negativity bias (overplaying your weaknesses). I’ll save that one for another posting. I do keep a very defined list of biases on a small piece of paper, and test myself, every time I need to make a decision. They include:

    – anchoring

    – confirmation

    – overconfidence

    – recency

    and I will be adding negativity to the list!

    Thank you


  46. Hi My name is Khaliah Ferguson,

    In the next 30-60 days I would like to have my Personal Shopper/Life improvement website and business running. Being raised in a lower income househould and environment there was a lot of social resources I lacked. As an adult it took a lot of reading and researching to find the opportunities I have found for myself and I’m still searching for more. I’ve always felt intelligently inferior because I moved into an affluent neighborhood and worked in environments that were socially and economically different from my experiences. I always worked in retail from sales to management but more in the cosmetic fields. I’m now a traveling makeup artist with Estee Lauder so I meet and work in large high end department stores from Neimans to Saks and all the rest.

    This background has shaped me as the go to person for all my urban lower class working poor associates, friends and families. Everyone has told me I should become a personal shopper, a blogger for navigating social classes for the poor etc. I must be honest and say that I use to reject this notion because I believed it wasn’t an honorable “smart” way to live and it brought higher insecurities in myself that I can never be that “respectable” lawyer, accounted get the picture right. That sounds like the typical job for a single mom with a two year associates degree, something I’ve been fighting to disprove.

    It’s apparant I have a gift for it so the risk comes with stopping my quest for approval as an intellectual paralegal and to ACTUALLY put some apples into what I do well in naturally. My risk involves taking a step back and working in the sales department in one of the department stores to get more clarity on how customers shop for clothes and to find a way to market my personal shopping and life improvement website for customers and sales.

    It appears that one client can change your life in an instant. I have read books that says target a targeted niche and the one niche that I know can benefit from such information is the lower working class. Being apart of both worlds allows me to see the gaps and missed opportunities for those who are socially outcast and from those I speak to daily at work. I’m always advising the working poor where to go, move, shop, act, behave, improve, how to raise childrens test scores, where they should shop for food and all of the above.

    I think this job is one that many would look to as “unstable” work since it’s not intellectually gratifying. Working with the lower class on teaching them how to navigate the tough world of pulling yourself up by your bootstraps is all about connections and small self improvements can be very rewarding and lucrative.


  47. I was a full-time employee for 10 years with one company and I found out I quickly reached my plateau within 3 years after joining the company. I decided to become a consultant after leaving this company. Consulting always has an inherent risk of unpredictable income. But I am glad to say that I learned more and did more networking in the last 3 years of my consulting life than my 10 years of being a full-time employee. Oh, did I mention that I did an all-paid international consulting gig for 3 months straight?!

  48. I am an Italian artist, producer and entrepreneur in my mid-30’s. I never studied English apart from mid school but I traveled a lot in my life, always alone cause I love to breathe culture, energy and life. I began to read Shakespeare’s sonnets at 12 and thru partying with girls worldwide, writing and singing songs in English and reading tons of books in English I slowly learnt it well. I have lived everywhere, from Shanghai to London to Rome to Berlin and Miami and established businesses in Italy and Uk. As side jobs I acted in theatre plays, made assistant director in tv series, sold French wines to luxury hotel and dance in club as image guy. I lost my father last year for cancer, but I have a strong mother and a strong fiancée. So what now? I got a label in London and I am about to launch my second startup in Tech City. Everybody told me to focus on songs production or business but I love th multiple slash aspect of life. But I agree I have to focus. So what the conclusion? I totally blurred the lines btw artistry and business and I am gonna launch my entertainment b2b startup in a few weeks, using my music and video productions as a go-to- market strategy for customer acquisition, partners engagement and exposure augmentation. I love risk, pretty managed and measurable risk each day, otherwise we would live in caverns yet. Seth Godin calls it lizard resistance. And as Reid and Ben said, we have to make a leap and take calculated risk to make an impact in this universe, bridging the gap btw security and progress. It’s called human evolution and now is the time the world goes on, beyond what we know. P.s. to expand to USA in the long term, Inhave enrolled a submission for 2013 with the guys at Blueseed. Amazing project.

    Cheers guys

  49. My next 60 days will be a continuation to something that started in May, while I was reading the Start-up of You: careful, yet determined, steps towards a new career.

    Re-thinking my career path is nothing new to me, for throughout my 7+ years of work experience I have been exploring different options from research to PR to event management to journalism. Some years ago I congratulated myself for finding the perfect path – immigration & media research. Then life happened: while on an internship in Ottawa, I fell in love, and 2 years later I immigrated permanently to Canada from Finland.

    Immigrating to a new country and adapting to work in a foreign language have been the biggest risks I’ve ever taken. The new life hasn’t always been easy, but taking the risk has provided me with a life full of love and happiness. Through hard work I have also been able to re-establish myself professionally, by switching from immigration research to counselling immigrants. A year later I found myself leading a team of employment counsellors, and I therefore thought my career was happily going the way I wanted to … until something happened this spring.

    What was that something? The Hoffman & Casnocha book.

    The book awoke my inner explorer, who had been hibernating after I had successfully settled in Canada. Suddenly I was again yearning for new challenges, opportunities, and learning new skills. I realized I had let work take over my life and career, and now it was time to show who the boss is – c’est moi. The book helped me to narrow down what I really like in my current job, and with plenty of thinking, researching and networking I have found a new direction for my career: diversity management.

    The transition won’t happen overnight, and at the end I might not even end up in diversity management, for maybe I bump into something more appealing on the way. Therefore I’m not worried about the end result – as long as it includes a happy me – and I’m just fully enjoying the journey, and utilizing the new energy and excitement I have.

    Based on my previous experience, I know that a career shift is not a risk for me; a bigger risk would be not to take it. I also know, however, that the honeymoon phase of planning a new career is not going to last forever. After sometime, if and when the shift will look more difficult than I thought, fear and doubt will try to oust optimism. However, such battles become easier to win with the support of encouraging, idea rich and creative mentors. Would be absolutely amazing if my mentors would be called Ben and Reid.

  50. First, thanks for a _GREAT_ post, so many awesome comments too.

    I feel it`s important to push yourself out of your comfort zone everyday, snap out of your habits that hold you back from facing new opportunities.

    I recommend everybody to read “The Flinch” by Julien Smith. It is about our everyday fears we face, that really are no threat to us. It`s just a primal behavior, flinching as much as we do.

    I believe his ebook is still free at amazon, google it! (no really. do it!)

    Within the next 45 days I will have:

    1. “Risked” giving up more control of my main business by outsourcing most of the operations I do not need to do myself.

    2. Pushed through the first stages of an Educational Non-profit.

    3. Traveling to Dubai to assess new opportunities and concidering a long term stay.

    4. Contacting potential freelance customers most people don`t dare to, offer them a solution to a problem I have identified.


    1. The risks of the first one is frightening emotionally but realistically it can be backed up by a well working system to make risk almost non existent.

    2. Risk wasting time if not getting the right coop-partners to support the project.

    3. Risk losing money relocating.

    4. Getting turned down.

    Never stop chasing, just change the way you chase!


  51. Good afternoon Ben and Reid! Thanks for the informative blog post and wonderful opportunity you’ve presented to all of us here to take advantage of. As an ENTP, risk and I have built quite the relationship over the 27 years we’ve known each other. I currently run an admissions team of 13 counselors for a university that primarily offers online courses. I’ve been with my current organization for almost 4 years (managing for 2) and have begun to get comfortable with my leadership style and confident in its effectiveness. I have seen great success so far and am truly excited about the career that lies ahead of me. It’s amazing what you learn about yourself in your first two years of management experience.

    Growing up in Southern California, I’ve always had a fascination with the east coast, NYC in particular. I’ve had the opportunity to visit twice in the last four years; the summer between my junior and senior year of college and the Christmas of 2012. To say I’ve fallen in love would be an understatement, NYC and I are having a full on affair…risky to say the least.

    The issue here is that my current situation is VERY good (and lacking risk). As they say, good is the chief enemy of great. In my current position I’m challenged on a daily basis, work with great individuals, make great money, and have a 5 minute bicycle commute from my apartment to my office in downtown San Diego. Leaving this situation to go clear across the country, without a job, seems to have ignited the flame that risk and I seem to keep sparking. I would LOVE to make a career move to NYC in the next 30-60 days.

    As far as how I’m thinking about this risk, I’ve found great success enlisting the help of my family and parents. (Happy Father’s Day Dad!) My dad thinks the best course is action is to travel out there a few times, setup interviews, and find a job before leaving my current one. My initial thought was to drop everything and go, especially because of the confidence level I have in the skills I have developed since I started working full time almost 10 years ago. I’m wondering if my dad’s negativity bias is causing us both to exaggerate the risks of a cross country move sans employment. I’m not sure if moving back to SD from NYC is a risk I’m willing to take, especially given the awesome job I currently have. Writing this comment is the first “yes” step I’ve taken today, I’m excited to see if the risk pays off!

    Thanks for reading.

  52. Some people take risk and think, “I took the risk, I deserve to have it pay off” yet they are surprised when things don’t work out.

    Taking on intelligent risk requires forward planning.

    Reckless risk and intelligent risk often look the same to an outsider looking in on your situation. Yet understanding the consequences and your own fears can reduce some of the negative effects if things don’t work out.

    Asking “what if” makes me prepared. (It’s even saved my life once!)

    A few years back I desperately wanted a break in the tech industry. I sought out the exact role I wanted skills wise. Yet it paid a third of a regular wage.

    I took the risk that this would be my ‘in’ to the industry. I took on an second job just so I could afford to work the day job I had chosen.

    I spent 2 years absorbing skills and working 96 hour weeks. Then 4HWW helped me make the jump with those skills into contracting way earlier than I had expected.

    Fast forward another 2 years & I’m ready for the next big move. I want to make the jump into a creative role in the tech industry. Business improvement & advice, developing products, putting my ideas to work. As an employee then a freelance consultant.

    Now I’m considering the risks involved. Can I afford to take a lower paid job like I have done before? What would happen if I aimed for the stars and tried to go straight into consultation? What would I have to give up if I failed?Will I enjoy the work, how would I get clients – the list continues.

    Dealing with multiple risks is tough. I’m trying to mitigate the ones that are most important to me first.

    I’m testing the work environment by speaking with founders and writing feedback reports on their products for free in my spare time. The feedback has been fantastic and I have loved it.

    I did a full audit of my finances and know exactly the level of salary that makes it or breaks it for me. This narrows my opportunities but because I understand the consequences, a lower paid salary is not a risk I can take.

    I’m testing my idea creation abilities by building my own products, going to startup weekends and I have even taken part in a startup incubator.

    Now I’m seeking the best opportunity aligned to the intelligent risks I’m willing to take.

    “Risk comes from not knowing what you’re doing.” ~ Warren Buffett.

  53. I’m Aussie Bryce from the great land down under. My next career step is to become the face of health in Australia by starting a lifestyle mentoring website that assists people in changing necessary facets of their daily lives that may be harming them. Often the face of health and lifestyle is a 60 yr old man in a white coat and glasses which is quite intimidating. I want to flip that perception and make health and lifestyle care inviting and thus easier to access. The risk of this venture is that people won’t listen to a 25 yr old bloke that looks like he is going to his first prom…but as I have encountered in everyday practice, people’s perceptions and mindset can be affected by a smile, confidence and most importantly a zest for something they are passionate about…assets that I have in spades!! I have been sketching ideas and developing videos, the next step is to create the website…something I have no background in but one that I’m keen to tackle!! Thanks for the article

  54. Hi guys. I’m the freelance writer you mention, happily bouncing along making a good living because I’m used to “hustling every day for gigs.” A journalist and speaker based in Sydney, Australia, I write for major newspapers and magazines in Australia, including for the Sydney Morning Herald (SMH) on careers and productivity.

    30-60 day goal:

    Make my income less about selling words (which I’m good at) and more about selling products (not yet good at). I’ve got an e-course and in-person masterclass ready to launch on stopping death by email. Everyone I know has an overloaded inbox, including, according to students of my business writing course at Sydney Writers’ Centre, those in the corporate world. I think my market lies there. I write about productivity in the SMH, and know how to manage what comes in, better write the stuff going out, and when to use other methods instead!

    Content is inspired by Merlin at inbox zero (his approach changed my inbox forever), Tim (what can I say, been using 4HWW tips daily since book launched), plus my own experience as a successful journo and wordsmith.

    Dozens of PRs email me daily and I know what catches my own attention. Meanwhile, I’m always aiming to ‘cut through’ so my own emails reach, persuade and build long lasting trust-based relationships with key editors or business partners. Basically, if I couldn’t write persuasive emails I’d be starving in a garret. I know what works and what doesn’t. Now it’s time to tell others. Would love your advice.

    How am I thinking about the risk?

    The risk is only a short term, time-based risk. Sure, I could use that time to sell/write other stories for more editors, but that will lead to more of the same – good income, fragile career, versus GREAT income, resilient career. (Tim, I realise I am sadly lacking my muse business!)

    Thanks for a great post. Would love to win this one.

  55. Hi all, my name is Emmanuel, an ambitious 24 year old from Zimbabwe, currently in the US. I’ve been toying with the idea of starting my own t-shirt line. i have a great concept and brand for the products and for years have been sitting on this idea but have put it off due to other obligations such as school, work etc and procrastination.

    In the next 30-60 days, I want to officially start up the t-shirt line, this means selling the completed product to customers. In order to get there,i need to produce the shirts go through the printing, branding and packaging process and have them ready to sell. I need to get boutique shops to carry my products as well as set up an online store and website.

    Up until a few weeks ago, i knew nothing about the t-shirt and clothing industry. Other than knowing what looks good, i really knew little about how finished clothing products were actually made. BUT!!!!! I decided to not allow that to be my excuse anymore and just started learning as much as i could.. I’ve been hanging out at clothing stores and studying fabric and clothing(gotten alot of funny looks for doing this) and also used the internet to find information I need. It’s weird how when you focus on

    something, it seems to some how come together. I heard about a creative fashion workshop at a local college which i attended yesterday and met some amazing people who are involved in the fashion industry. So not only was it an awesome learning experience, but it was also a great organic networking opportunity that also opened my eyes to things i hadn’t thought of yet. These things will ultimately strengthen my brand.

    I also really like the idea of “working for free” which you mentioned in this post, as you said “learning and networking is key in business” therefore, I could learn a lot about the ins and outs of the industry this way and will probably find a local fashion company to intern for in the next 30-60 days. I have also banned myself from using the word “no” and for this week will say “yes” to everything.Ok, maybe not everything, but i will exercise the power of “yes”.

    I have realized that i am the only person stopping myself and decided to just get on with it. Risks associated with this move are financial risk as i would have to invest my savings into this project, (however that is a risk that i am not afraid to take as i feel the investment would be worth it in the long run). There’s the risk of people not liking the shirts, boutiques refusing to carry the line and the line not being as successful as anticipated. but so what???!!!!the only real risk here is failure, but id rather take action than risk looking back and feeling like i could’ve done more.

    I feel motivated by this post and now i know who Ben and Reid are, so shout out to Tim for that. (you can always rely on something helpful from this blog).

    To expand on risk-taking and feeling comfortable with risks, a recommended read is “The Art of Being Unreasonable:Lessons in Unconventional Thinking” by Eli Broad and for people like me who have ideas their sitting on and need an extra nudge to get up and do something about it,I recommend “Making Ideas Happen” by Scott Belsky and off cause “4 Hour Work-Week” for anyone who hasn’t read it yet (do yourself a favor).

    have a great week all..

  56. Hey guys,

    Thanks for the post.

    I’m from Moscow, Russia. I’ve always wanted to be an international

    professional so when I was 22 I moved to China, the new promise land. I’ve lived here for 3 years and now work for one of the top Chinese companies. I can’t tell you how proud of myself I am. Few foreigners get to experience the real corporate culture in the traditional Chinese company where nobody speaks English. Is the experience different from what I expected it to be? Well, the word different is not strong enough in this case.

    I know that my job doesn’t garantee me a good life long term – even laws in

    China change every day. So I don’t get too comfortable and look for new opportunities.

    I think that we should accept taking risks as part of the lifestyle, but I don’t agree with taking risks if you can’t afford it. Anything might happen. And according to my experience, when you are not prepared financially something is more likely to happen to you.

    You can easily take risks when you have money and stability. That’s one of my priorities. My desicion making process becomes a lot easier and faster – I don’t hesitate and say yes or no to proposals without fear of losing anything. Instead I consentrate on things I can benefit from.

    And of course the fact that I’m a young woman makes me take care of my

    safety even more: it’s harder for a woman to get a legitimate well paid job

    where man treat you as an equal professional (especially in not very developed countries). Lots of things are more complicated for me: even in China I have to pay extra to get visa, and I need to justify my life here especially because of my age. Being a woman I’m gilty until proven otherwise.

    To change my life and professional development I decided to keep my well

    paid job and start online consulting for foreigners that are eager to come to

    China to pursue their international carreers or learn more about the real Chinese culture (I started working on this project thanks to Tim’s 4HWW. Tim, you are awesome! I learned about you from my Russian friend who you met in Beijing).

    Tim, Ben, Reid, I’d really apreciate if you chose me!


  57. Thank you for the inspiring post. I have taken a huge risk by not re-entering the workforce as quickly as possible. I was laid off in 2009, and decided to start my own business. My first 3 attempts were failures, but I learned a lot in each case. My fourth attempt, I hope, will be a winning success. At this point it has to be, because I think that I am too long out of the workplace to re-enter in my previous job title. The current project is e-commerce. I plan to have multiple sites up selling multiple products. I look forward to any insight you can provide.

  58. Hey fellas,

    Thanks for the opportunity and many thanks in advance for reading my entry.

    A little history about myself:

    Currently employed, making a fantastic salary at a start-up company. I’m on the verge of implementing software and workflow processes that will change the way our parents receive healthcare, the way we receive healthcare, and dramatically change the way our children receive healthcare.

    For the better.

    I still get job offers on a frequent basis, completely unsolicited; much like Hans Keeling before he started Nexxus Surf. I pass these job offers to my friends and watch them undertake new, exciting opportunities equal to the monetary benefits of my current position. They laugh and ask what I do to get these offers and the answer is unbelievably: nothing.

    It’s all very rewarding and fulfilling- yet I’m still not satisfied.

    My real passion is health and fitness. I dream of helping others change their lifestyle to be one of health and happiness fueled by lifestyle and comradarie. As a former 24 hour mountain bike racer, I love the thrill of dedicated pursuit of, well… that’s the funny part: anything. I love the pursuit, not the prize. Maybe that’s the difficulty I have in staying at a job.

    I wholeheartedly believe I am capable of greatness, greatness worthy of history books (or e-books, as the technology goes) but only if surrounded by honest people dedicated to similar passions and mentors to help me navigate the questionable waters ahead.

    So what is keeping me from it? Maybe as Tim states in 4HWW: unfounded fear. A tolerable existence is more comforting than the unknown, even though I know the worst-case unknown is still not as bad as scenarios I’ve already overcome. I’m a geek at heart, and bring with me the common trait of many of my brethren- stick my head in my monitor and suffer alone in silence. Having identified this as my weakness, I’ve taken action to overcome it- I’ve joined a local group of entreprenuers to network with others successfully doing what I dream of. I’ve joined Toastmasters to learn to be a better speaker and to better communicate. I attend meetups and learn new skills that better position me to accomplish my goals. What I don’t do is “network” at networking events. I don’t take the step needed to execute. Fire power up the wazoo and I don’t pull the trigger. In short, I’m scared.

    On Tuesday, I have a meeting with a “Business Incubator” firm to discuss my ideas. I live in a small town filled with upper-class folks that perfectly identify my target market of opening a CrossFit gym that would allow me to pursue my passion of helping people reach their fitness and nutritional goals and build their own self-confidence and self-esteem. Getting that off the ground would allow me to focus on my nutritional planning software that simply “gives” people the menu and grocery list they need to meet their dietary goals. This software differs itself from others in the same category in the fact that it simply tells you what to eat rather than offering you thousands of confusing choices that might fit your goals. Both of those items have exit strategies and plans to extract me from the day-to-day operations, while still providing me with a diversified income and relieving my family of the stress that a single misfortune in any one area can have a significant impact on our quality of life. Even after exercising my exit strategy, I’m not content to sit on the beach picking my nose for the next 50 years- I’m prepared to continue on with my “to-do” list, each project building upon the successes of previous events and undertaking new ventures and goals, all the while further diversifying my income stream.

    So what’s holding me back? Well, my current job- it is very exciting. It has potential to fulfill my personal goals ten-fold over my own ideas. I question where the commitment of our executive team is though. I think their commitment is to the IPO, not the business model we preach. You know what scares me most about that? The things that irritate me the most are the negative traits they exhibit that I recognize in myself. We spend a lot of time herding chickens. Either that or I’m just scared and willing to endure a tolerable existence over the unknown.

    If chosen as the winner of your contest, I’d like to pitch my current position- it’s potential as a company, it’s potential to me as an individual employee and pitch my business plan for my personal growth. We would then discuss the pros and cons of each and how my own personal strengths and weaknesses line up with those objectives. With that information, I would hope to provide you with a realistic perspective of my own personal “state of the union” and eagerly listen to your advice.

    As I walk away from our meeting, I would hope to have a clear picture of what you believe the best course of action is, as well as how I can leverage my network of peers, mentors, and friends to best position myself for success. Also when and how I should create “milestones” to make sure I don’t wander off-track and start herding chickens of my own.

    I’m not looking for someone to tell me what to do, or layout a step-by-step plan- that’s called a job, I have one of those. but to point me in the right direction with a smile and a nod- just enough to bolster my own self-confidence.

    Thanks again for your time and attention.

    I honestly and sincerely look forward to hearing back from you.

  59. After graduating from business school, I took a position with a technology firm as a business analyst that paid me much less than I was expecting. The decision to sacrifice a higher starting salary was made easy due to the company’s growth potential and my ability to learn a new skill in an industry I wanted to stick with for the rest of my career.

    After about 2 months in my analyst role, I was offered a position as director of a major revenue channel at the company. While initially feeling completely over-my-head, I learned as much as I could about the channel and put all of my effort into turning my piece of the business into the most profitable channel in the organization. Over the past few months, my channel has led the company in revenue production and has allowed us to continue our impressive growth curve.

    While my channel has been extremely productive since I took over control, I’ve still been paid my initial starting salary. There’s no doubt that my production to the company has come at a discount, and I feel like the time is right for me to ask for a raise. I’m going to approach the conversation in a scientific manner, presenting the hard revenue data to back up my case. The initial risk I took with my pay grade paid off dividends in term of my learning, and I believe it’s time to ask the company to recognize my commitment.

    Thanks for this post, the advice has been extremely helpful and motivating!

  60. My risk is that I may be giving up great for just good. I have an amazing job running a foundation that supports people that are changing the world and I wrote a book last year for people that work in nonprofits that has allowed me to travel around the country, helping young professionals take the risks that you talk about.

    I feel like my next big step is developing a side gig of helping social entrepreneurs figure out how to maximize the social good of their efforts as an advisor or board member but I don’t yet have the connections or social capital to make this happen at the scale where I could make the greatest difference. Because I have been successful in my work life, it feels really risky to start doing something where I will be starting from scratch, even though I believe in it 100% and know that I can add real value to the efforts of social entrepreneurs. It would be great to have your advice.

  61. Hey All,

    Can’t wait for the book! Some fantastic comments above!

    I’m an Accountant and got into the profession for security. I lacked confidence and a voice. I’ve worked on it for years and now am just about to finish an ebook for people to take control and live a confident and abundant life. It’s about taking control, being innovative, communication and a rejuvenated future. It’s founded on my own personal story of sitting in the rain exhausted after working long hours and not knowing why. The book doesn’t slate any professions, it’s about empathy and inspiration to lead the new economy and live with an abundant mindset.

    The risk is in putting my own stories and it was hard. I know it will help so many people. The other risk is i might be thinking too big…i want to inspire now, then change the way safe professions communicate in order to help them into the future. I would love to lead a community in using their skills to make a difference in developing nations. Big dream so i’ll go after it.

    I thought about the risk…i can hang onto my secure job and risk being passed around and not be myself. Or i can lead and make my voice heard!

    It’s time to make a difference and stop shying away I think!

    Have a great day

  62. Great post. Thank you, Tim, Ben, and Reid.

    I am a mid-30s MBA who has worked for some of the greatest companies in the world: JP Morgan Chase, McKinsey, Apple, and now one of the hottest startups in Silicon Valley. By any conventional definition, my life has been a success.

    And yet. My career has generally been unsatisfying. I fundamentally believe this is because I’ve been unwilling to take enough calculated risks.

    In the next 2 weeks, my boss will be leaving my startup. My role will be redefined, and I would like to use this as an opportunity to ask for a promotion. I’ve never actually been promoted (my career advancement has come entirely though changing companies), and the idea of asking scares the crap out of me.

    Bigger picture, I hope to use this opportunity to break a 12+-year cycle of letting fear, rather than opportunity, dictate my career decisions. And I am prepared to be held publicly accountable for my future risk-taking behavior (I’d be willing to submit periodic updates). I’d be thrilled to be your guinea pig in exchange for the coaching you offer.

    Thanks for your consideration.


    After graduating in 2007 I accepted a position at a law firm in Invercargill (southern most city in the world). I have quickly risen through the ranks and have been told in no uncertain terms that if I commit to the firm I will become a partner in the short to medium term.

    Whilst I am lucky to be in that position, the thought of doing one job my whole life (as committing to partnership would entail essentially a long term committment) has been playing on my mind and is really a hard pill to swallow.

    So my dilema begins. Do I resign myself to life in my current role, in my current city and enjoy the benefits of financial security for my future, or do I make perhaps a stupid decision and take a punt on something else.

    Add to this the fact that the UK and European economy is teetering at best and my decision looks to be easy. Stay put and be sensible. But…

    The fear of not challenging myself and taking the path of least resistence leaves me with an uncomfortable feeling of not knowing what it would have been like and whether I would be better for it.

    After much pained brainwork I decide that I have no option but to run the proverbial gauntlet and make the move even if that decision is inheritantly risky for a multitude of reasons.

    Fast forward to today and I have a one way ticket booked to the UK with no job lined up at a time when many firms are saying things like “recruitment freeze” and the like. To say that is a scary prospect and that I have butterflies a month out from my departure date is a massive understatement. But as risky as it is leaving a cushy job/career path and heading to an economy on the brink without a job or a place to stay I know that deep down I have no choice but to take that sort of risk.

    What nailed it for me was the thought of jumping forward 20 years and still sitting behind the same desk having not done it!

    thanks for the article and the opportunity to put my thoughts into writing.


    June 2012: My mom has been unemployed since Jan 2012. I am leaving a 250K+ per year job (high profile corporate job) to build a business with my mom; yes, I am leaving the security of a quarter-million dollar a year job to be an entrepreneur with my mom. (And yes, I offered to simply support her, but her dignity rightfully demands that she contributes to the world, so because she can’t find a job, I am creating one for her, as a business partner, with absolutely no second thoughts). Full circle: Was an entrepreneur before corporate America; gave that up for “security” (and 14 hour workdays 6 days/week) but now that my family needs me, I am back 100% full force to start a new business that will allow my mom to never be a wage slave again. The two most important life goals: #1: Be a good person, #2; Take care of your mom, ALWAYS. Risks? Insignificant when I consider what the upside will be.

  65. My goal is to launch my (overdue) career as a freelance writer in the next 30-60 days; obviously, I feel very affirmed by this article! Specifically, I aim to complete my website and garner at least three clients in that time. My first love is fiction, but I also have a talent for blogging, copywriting, and article writing, and this is where I will begin marketing myself first.

    I have long dreamed of supporting my family with my writing, but well meaning pragmatism and fear of risk have tripped me up time and again. Thanks to the works of Steven Pressfield – and now this article – I am beginning to see risk as more of an affirming factor: If there’s a healthy measure of risk and fear surrounding the goal, then it’s probably exactly where I need to be.

    Thank you for the encouragement!

  66. My whole life has been one big risk even if I wasn’t aware of it. I grew up on the south shore of Long Island to a lower middle class family. My parents have worked their butts off trying to make ends meet to support a family of six (four children). After graduating High School, I realized that I had an innate ability for creative writing. I craved literature. I was curious about all facets of life. I wasn’t exceptionally great at anything, but I was certainly passionate about many things: music, philosophy, poetry, film, science, art, skateboarding, sports. Somehow I knew that all of these were interconnected. I was nineteen years old and I decided that I wanted to become a renaissance man…a renaissance man? It’s true. I received a bachelors from The New School University in Liberal Arts; Riggio Honors: Writing and Democracy program. I also received a Certification in Screenwriting for Film and Television. I then earned myself an insurmountable mountain of student loan debt…I was enslaved. I had no idea what I put myself into until the day student loans began rolling in and I couldn’t find a full time “career” because I lacked a technical discipline and the job market went splat!

    Odd jobs. I began picking up odd jobs that felt damaging to my espiritu. I’ve done everything from ripping up cat pee carpets to shlepping wine boxes in a basement while being timed to do so. Terrible jobs that I hated then but realized later, added dimension to my character. I went on interviews that were clearly ponzi schemes right off of Craigslist. Of course when they called me, I wouldn’t take them. That’s not how I roll.

    During my pursuit of “happiness,” struggling to pay off student loans, while feeling like a damn loser because I didn’t have a “job” to move out of my parents’ house, yet knowing inside that I was a champion, I stumbled upon a very important TED talk by a man named Tim Ferriss. I decided to do more research on him and quickly noticed that he was a fellow Long Islander. Of course, having never met the man, we shared a common bond. Long Islanders sort of have that interconnectedness. It’s a small island but big in heart. I bought his book, the four hour work week. I read it and it became a manifesto for me. It was exactly what I was looking for. It wasn’t so much the idea of a 4 hour work week that caught my attention. It was the idea of being an entrepreneur. And I realized then that I should go balls to the wall and start a business. Only problem was…I had zero money. Absolutely no capital. Literally. I had a Chrysler 300, that I couldn’t pay at all (I learned a very valuable lesson “owning” that car…no one cares what you look like! Fabricating an image to “look” cool in front your peers is a foolish way to live life). Luckily for me, during that time of plight, a drunk driver crashed into my parked car in front of my parent’s house and totaled the Chrysler. The whole loan was wiped out and I received roughly $3,000.00. I took a portion of that money and I incorporated my business. The other portion went to student loans, and the last portion bought me a ticket to visit my brother in the San Francisco Bay Area (my second time to Cali, but my first time taking a flight by myself and my first time to San Fran area…I’m travel deprived). While there, my brother took me to San Francisco. I saw the Golden Gate Bridge, massive with the beautiful cliffs dropping off to the Bay. We ventured over to City Lights Book Store (I love the Beat Generation). I felt a sort of liberation. It’s amazing what traveling will do to a person’s consciousness. It broadens every aspect of the mind. San Francisco…that place is paradise. Big Sur…well, it’s no wonder why so many great literary artists took to that place.

    Upon coming back to New York, I realized that I was going to have to face my fears; my debts, my inner struggles. I’m an underdog in this battle to win back my freedom. Thus, I began hustling, finding clients. I landed my first client in November 2011 and I tasted the money. I tasted the freedom. I was like a seawolf tasting its prey. I made more money working on my own this past year (not that it’s a lot, but it certainly is a valid sign that I’m headed down the right path) then I have all of those years in dead end jobs.

    Which brings me to today. Nothing is determined in my life. I’m constantly being molded. I’m constantly learning and I embrace the experience. I just don’t want to live in an impoverished state any longer. I’ll do anything to become a better person. I’ll do anything to be a champion and make it to the top. The question isn’t how…it’s when.

    In Conclusion, I never really had a mentor. I feel that this would be a perfect opportunity for me to bounce real ideas off of successful entrepreneurs. Perhaps you could be my mentor for 30 minutes.

    It would be greatly appreciated.

  67. The timing of this post is perfect. I currently work as an HR coordinator, and while it pays well I am tired of the cubical. I am in the midst of finding an ESL job in China so I can reduce my living expenses and work hours. With the extra time I will be able to focus on writing and internet marketing. I am very excited for where life is heading.

  68. Thank you for the post Tim.

    I’m a college student finishing a and looking into medicine, but getting distracted by Sillicon Valley / tech entreneurship.

    I’m envious of people like Tim, Reid Hoffman, and others that create things that millions love.

    I love all the success stories and hype surrounding startups as it helps me picture myself pursuing this. I realize it’s easier to start a company now more than ever. All of that stuff is great and all, and again, I’m envious of people pursuing their businesses. Personally, I’m trying to force myself to be realistic and humble, and seek the most practical path. There’s the 1% that are smart, resourceful, ambitious, lucky etc.. while the rest that tried and didn’t cut it. I’ve done nothing of merit that would suggest I’m in the 1% and very little of my skills transfer to my desired career change. I’ve decided that I will work towards a conventional and reachable goal that is risk-averse (getting an MD), while working on a product (an app) on the side. I’ve decided not to quit my future day job.

    Some of my thoughts and conclusions (written haphazardly) after reading the blog post are below. I would love to be told I’m wrong.


    So what this post is saying is no career is truly stable and one should prepare for “external shocks”.

    I don’t fully agree with the “resilient” career being better than the supposed “fragile” career. Firstly, if the government worker or the magazine editor takes intelligent risks to better their position in case of possible disruption (follow your advice), they would be training their resiliency with the comforts of a stable income. This is assuming they will in fact lose their job. Also, what about the freelancers that are getting their asses kicked with the constant instability and obstacles of freelancing? The ones that fail as freelancers will go back to a stable or “fragile” job. So aren’t the ones that succeed in “resilient” careers naturally gifted with the traits of survival and resiliency?

    Risk and stability ties into the college degree issue.

    Lately, a lot of criticism has been placed in the necessity of a typical college degree (which I totally agree with). I like the idea of being prepared for the work force with a skill (engineering, science, etc..) and getting hired for that skill instead of a piece of paper. However, bachelor degrees are useful first round filters. Do you realistically see them going away in the next couple of years? Maybe in agile industries like tech, but not anywhere else. Current students like me are stuck with the status quo. Nowadays a BA or B.Sc is no guarantee, and getting a higher degree like a Masters is necessary to increase chances of employment in many fields.

    Still, there are timeless degrees, yes? Medical degrees. Or maybe even law? Doctors will always be in demand as long as there are sick people. At least in North America, there will virtually always be a job there for a North American physician (perhaps you may have to practice in smaller town).

    As a bonus, not only do you have domain expertise, you have the all-important paper that proves it and opens dozens of doors into different career paths.

    Compare that with the meritocracy/”no degree” talk coming out of SVally (which I really want to believe). Sure, if you’re incredibly smart like Zucks or Gates and have built an incredible product that people are interested in, you can drop out. Or be incredibly brilliant and become a Thiel Fellow.

    What about all the people whose efforts are ignored. Whether the thing you build sucks or just doesn’t grab investors’/employer’s attention. I hear “Similar Work Experience” + examples of your work can subsitute the lack of degree for job positions. However, what if the work experience doesn’t produce anything impressive? Using the 4 years to get a CS degree to get past the first filter in a Google job application or get directly recruited seems worthwhile and helps your chances.

    [I heard some people with computer related degrees have trouble finding employment even with the supposedly huge demand from tech companies. Is this true? Isn’t a lack of a degree a huge disadvantage assuming you’re not the blessed 1%?]

    Success seems to happen to the 1%. Alternative paths to success all seem to rely on the individual. Their intelligence, perseverance, luck, etc.. is it not arrogant and naive to think you are special and belong in the 1% when so many others have failed thinking the same thing? The argument to this would be that you should at least try. You can always recover and revert if you fail.

    Here’s a scenario: Your original plan was to become a lawyer. You have a change of heart and drop out of college and bootstrap your iPhone app through freelance web work. As the years go on, your freelance business struggles to stay afloat (because it’s incredibly hard or external disruptions like cheap international outsourcing crush you), your iPhone app hasn’t worked (because customers don’t want it, App store does not like you, or the tech bubble bursts), and you’re approaching your thirties with debt (family, stability, and supporting your loved ones are becoming priorities). I think a normal person would give up and try to get a stable income, instead of trying to revert to the lawyer path. 4HWW gives you the tools and examples to redesign your life, but the individual has to have the smarts and focus to succeed.

    Wouldn’t getting the law degree first and then starting work on an app be the smarter choice?



    I wish I was the 1% that is smart and resourceful enough to succeed in whatever they desire, but I have no evidence to support this. Therefore, I’m going down a conventional path to stability while working at breaking into the 1% on my downtime.

  69. Before my comment for the contest, I want to challenge the view that “Unless you take frequent, contained risks, you are setting yourself up for a major dislocation at some point in the future.”

    While I agree that “Today’s world is full of change and unpredictable disruption,” I would argue that such unpredictable disruption occurs in predictable areas.

    That is, I know that employees with careers in the tech startup world are going to be rocked by volatility and disruptive technology, over and over again. For employees in tech, then, it is wise to branch out frequently, mitigating the long-term risk that comes with never taking short-term risks.

    But what about CPAs?

    I know, I know: “But the print industry seemed stable, and nobody pre-personal computer could have predicted that print would die.” That’s good supporting evidence for the premise here…but an important point is that the print industry was still dominated by people with “soft skills.”

    I challenge anyone to offer a historic example of volatility that left employees with quantitative skills (engineers, accountants, etc.) wishing they’d better prepared themselves to “absorb shocks.”

    What shocks? This post makes a very nuanced but important point…I’m just not sure that it applies to everyone. The reality is, many employees will never have to worry about hustling or taking risks because their livelihood is protected from shocks.

    My risk:

    After graduating with a degree in marketing last month, I am applying to teach English abroad for one year in southeast Asia (either South Korea, Japan, or Taiwan).

    Many of my friends with undergraduate business degrees are going back to school in the fall to earn an MBA. Living in a foreign country instead, then, feels risky to me because I know I could be using the time to add another line on my resume, a pretty acronym to validate my business acumen and put next to my last name.

    An important point about negativity bias: it’s at its worst when you go against what all your peers are doing. Not only do I worry what will happen if I’m making the wrong choice, wasting a year, foregoing a master’s degree, etc. – but I worry that everything will go wrong because I’m DOING SOMETHING UNCONVENTIONAL.

    In reality, I consider the upside and I think that becoming conversationally fluent in a foreign language will differentiate me just as much as an MBA and open up opportunities down the road beyond the USA.

    Meanwhile, I want to test various business ideas I have. If I can personally visit a product manufacturer in China (per the recommendation of a few Muse case studies), that would be great.

    Finally: a note on risk and uncertainty. They are not always the same thing. I think that a risk–like investing in the stock market–always has uncertainty in the sense that I’m uncertain whether I will profit (desirable!) or take a loss (I don’t want that!)

    …In life, however–unlike in the stock market–uncertainty doesn’t by definition involve risk. Risk implies the possibility that one of your predetermined “I don’t want that to happen” events might indeed happen “to” you. By contrast, I am excited to travel precisely because I’m not sure what is going to happen…and in my uncertainty, I don’t have an outcome I’m chasing with the “risk” of not getting there.

    Taking career risks–or in life, embracing uncertain situations–begets a feeling of control over your own destiny. Uncertainty is inevitable; you can either pursue it intelligently or wait knowing it might turn everything upside down on you. And when I do choose a situation with uncertainty, like Peyton Manning choosing to play for the Denver Broncos then addressing questions about if it was the right choice:

    “I make a choice,

    Then I make it the right choice.”

  70. This is so true – Its all about risk taking – I started life as a Pharma Sales guy in the North of England 20 years ago – By taking 4 risks – I have now worked for Xerox, Apple, Microsoft, Motorola and Dell in Beijing, Shanghai, Hong Kong, Dubai and now Singapore – So 20 years and 5 huge Technology giants in 5 great locations

    – how did this happen? with four unconnected risk taking moments that decided the flow of my life events and scared the life out of me when I made the tough call

    1) As a Phara sales guy in 1983 straight out of college I made a big bonus one year and instead of a holiday, car or house – I invested in a Cheese and Wine shop in Sheffield with my partner -worked weekends, evenings and all my holidays to learn the trade – I was young and did not need sleep – thats why apple hired me – more on that later – we also become runner up for young business person of the year and met prince Charles – made no money but learned retail inside out – sold out for nothing

    2) In 1989 I was a bored Phara Sales guy that loved IT – so I took a 80% reduction( did not cover my mortgage ) in Salary to be Xerox sales guy, – I loved it became the top sales guy – the bets in the office is that I would fail in 3 months – It was hard and stressful my patch was the same area the move the Full Monty was based on and the same year

    3) Xerox offered me a job in Dubai with a distributor just after the first gulf war that nobody wanted – but one way – I could no come back – so I jumped on plane with two suitcases became the top sales guy in the Middle East – so they sent me to China in 1996 to do it all again – again two suitcase on a plane no way back

    4) in 1999 after 10 years with Xerox now in Hong Kong – Apple offered me a job as the retail guy in APJ – because of the Cheese shop in Sheffield – but as the headhunter said this Steve Jobs has just come back – it could be a disaster or it could be okay buts its a risk – your decision – so of course I thought I have to take the risk – whats the worst thing that could happen – they fire me but by then I know all about PC’s

    Thats been my mantra for 20 years – take the risk – whats the worst thing that can happen – I get fired 🙂

  71. Totally agree with you guys, especially on the evolutionary aspects, which affects us in so many other ways as well… So here’s my “anthropology”:

    I graduated with a BS in Mechanical Engineering just a few days ago. Until very recently, I was working as a part-time contractor for a reputable company, and was well on my way to becoming hired permanently. The company policy makes it very difficult to fire people once they get hired, which is part of the reason why many employess have been around for decades.

    One day I got a call and was told that my contract had been terminated (30-day notice). Though my boss never officially admitted it, and my work was actually well-regarded, it must’ve had something to do with me walking into my boss’s office, telling him that because I’d like start my own business, I would like to continue working no more than part-time after graduation… Whatever the reason for ending my contract, it’s all in the past now…

    So now that I’ve completed my degree and should be seeking a well-paid full-time entry-level position at a different company, I’ve spent the last few days focusing more on finding a part-time job, meaning that I’ll be poorer than ever … “What a waste!”, you think? Perhaps, but the biggest benefit I’ll be getting in exchange for my labor (or lack thereof) is something many top-executives can only phantasize about: time.

    I will use these 20 “additional” hours of time per week to invest in myself, and build my own company.. The 4 Hour Workweek shall be my guide…

    The reason why I’m taking this risk is because I don’t want to miss out on the opportunity to design my own lifestyle (which is now, not 20-30 years from now). Sure, things could go wrong, and chances are I might fail several times. But there’s just so much to learn, that, worst case, the only reward will be the experience I gain from it… To me, that sounds like a risk worth taking.

    Thanks for reading,


    P.S.: Tim, this is all your fault – and I thank you for it : )

  72. This post require further research to dig into certain things that affect most individuals especially those who have financial related commitment (a family, a mortgage).

    I strongly recommend taking further actionable insights to reduce career risk:

    Career mismatch can be persistent if you do not know your strength and passion:

    1. I strongly recommend that the individual use existing tools (MBTI,, to figure out their human capital assets.

    Do note that human capital can be acquired overtime BUT you have an innate rate of learning on certain areas faster than others. Thus know what is it that you are good at.

    2. Figure out the risks inivolved in transisting your career.

    E.g. how much does it cost to give up a job and move into another? Family time? Money? Health?

    Not everyone can afford to follow their passion if they do not manage other equally important aspects of your lives. To figure out this, please stay tune to future products that can quantify those risks and address them with measureable insights., and other similar social media sites have rich dataset but it is a pity that they did not hire a labor econometricians to tease out the above insights and help people enhance their lives with existing information.

    There will be more interesting new apps that are coming into this market if these firms do not pay attentions to the above real news in resolving career mismatch persistency using information that have exist in their platform!

  73. In theory, everything works. Everything makes sense. And everybody win.

    But 98% of the people reading this post will do nothing. They’ll go back to their same lives and within a week everything will go back to normal. (they might talk about this once or twice within the next few days, but that’s it)

    There are people that will do. And it doesn’t really matter if they read this or not. They’re just that type of person.

    Eventually people will reach a point where they go ‘screw it, i’m just going to go for it.’ I haven’t read a single account of people being able to trigger this, but it’s not like posts like this aren’t useful.

    Shut up, and get to work. Please.

  74. I found an interesting thing today: a way to keep my heart full. It isn’t with hugs or kisses, with having sex (although that does help), or with catering to myself, my needs, my wants. It was by donating $62 to see something cool that could possibly be done, be done. (See Seth Godin’s new Kickstarter project).

    I’ll evaluate risk like this: if it is worth paying for the possibility of a certain product or service, than it will be worth paying for the actual product or service.

    As for me, I’d like some help turning my website into a series of some sort. I’ve already quit the day job, but a 24 year old Assyrian woman needs a bit more practical guidance. I’m relatively abstract and full of ideas.

    Ps: Tim, thanks for giving a girl a good push.

  75. Good post, and great idea to get people writing down goals/ ambitions… certainly helps you make them happen!

    My risk is quitting a good and safe job in the very shaky banking industry and world economy. Having got married last year and had our first child 4 months ago, timing is challenging when I “should be” going for the safe options now, but I figure, if I don’t do it now, I will never do it, and wake up in 10 years time regretting/ resenting my life. So I’ve decided I’m going to go for it, change lifestyle to spend more time with the baby and my wife, as well as pursue other business ventures…

    – What change am I making in the next 30-60 days?

    After a lot of soul searching, I have handed in my resignation, I’m now half way through my 3 months notice period so will not be a salaried person before the end of the 60 day period!

    I started this journey over 12 months ago, having made the decision on my 30th birthday to build the life I wanted, not accept the one I had. Cue lots of sould searching and self experimentation to make me better/faster/stronger, which like any self respecting internaut I recorded on a blog (see link on my name for the steps I took to get in a position to quit last month).

    Over the past 12 months I have found ways to maximize my energy, motivation, get fit, learnt tons of useful skills, realize what’s important to me and regained control over my life. Guru’s like our Tim, Mark Sisson and Tony Robbins all helped on the journey (and will hopefully keep helping in the tough times). I also did lots of learning by doing, like setting a tan through polo shirt company called Patrice Wheeler just to try out creating a business, and a contact lens case with a mirror and date function built into it (so you never forget when you put your disposable lenses in!), very originally called lens date case, so I could try out crowdfunding. Learning by doing, by getting out there… a great concept.

    – How am I thinking about the risks involved in this change?

    I can really relate to the Rick Hanson quote and I spent ages over estimating all issues/threats/ road blocks, and did not focus on the upside of what I wanted to do: change of life to actually live life daily, not just exist. I recon when you have a strong enough goal and you really believe in it, the risks and threats diminish. Once you understand and accept your downside, you just have to get yourself in position and go for it.

    So emotions have really fluctuated from “lets go, go, go!!”… to “what the hell are you doing throwing away what you’ve built!”. The reason for the blog were purely personal: record my trials and tribulations to give me something to look back on. Seeing how far I’ve come along has enabled me to realize I can take that crucial next step: quitting. The initial mountain involved in making this happen looks a lot less steep now I look back at it, which makes the road ahead (and risks associated) seem a lot less daunting.

  76. Wow, I finally reached the end of the comments section! It seemed like it went on forever – which is so truly inspiring, to read about so many people taking risks in order to pursue their dreams and live happier lives.

    This post was great, thank you guys. I think I’ve been taking risks for some time now. I graduated school last year with a honours BA in Communication Studies and Professional Writing. I originally applied for these programs thinking I wanted to get into advertising – I envisioned working for a cool marketing firm, full of young people, getting paid good money just to use my creative thinking talent. Now that I look back, it amazes me how my vision was to work for a company. Not to own anything, not to be wealthy, not to do anything out of the ordinary – simply to land a cool, well-paying job creating ads for products and corporations. I dreamed of being being an employee for the rest of my life. That’s what school taught me – that’s how the system taught me to think.

    Gladly, I slowly woke up during my first 2 years of university. I think it was a combinations of spiritual epiphanies, with a hunger for wisdom, that led me to realize I wanted nothing to do with the advertising industry and with using my talents to trick people into buying things they don’t need.

    I stayed in school because I didn’t know what else to do – and of course, I didn’t want to disappoint my parents. Plus, I have to say I enjoy learning so much, that going to school was always kind of fun for me. So I decided to make the best of my experience, since I’d have 2 more years to go anyway. I started taking extra courses about things I always wanted to learn about, like Celtic history and astronomy. I went on student exchanges to Italy and Thailand. I realized the world has so much more to offer. And I realized I had so much more to offer the world.

    So, long story short, I have recently opened my own photography business (, after having the courage to quit my other meaningless part-time job at nightclubs to turn my lifelong passion into a career. And I have also partnered with two friends and launched a life coaching company targeting youth in transition. Yep – we want to inspire, motivate, and guide young people graduating from high school or college to travel more, identify their passions, and create a plan to pursue fulfilling career paths. Our vision for the company is so innovative that a lot of people just don’t get it. But those who do are immediately impressed by our willingness to take the risk of starting something like this. Our company is called WIDISM – wide + ism = the philosophy of living life wide, the principle of embracing new possibilities, the belief in being optimistic and open-minded, the practice of life-long, self-directed, experiential and experimental learning and development.

    I’m only 24 years old but I already know that I will never again succumb to doing something that I hate or that has no positive effect on the world just to make money. My life is way too special, and so are my talents. And I’m committed to taking any risk necessary to ensure I can use my gifts to do good and to live a life I love.

    I hope my story inspires others and other comments have inspired me today.

    Thanks Tim, Reid, and Ben for the work you do!

    Camila 🙂

  77. I’m currently a mid-level manager with a major CPG manufacturer. I have spent most of my career successfully managing people in many different roles, as well as mentoring others on the skills to be a successful manager. I love working with people, helping them grow and watching them move on to be successful in other roles.

    Though I have a stable, well-paying job, and like what I am doing, I don’t love it. I’m looking to make a career change that allows me to take my people and managerial skills and share them with others, which is where my passion really lies.

    I would think this would require a transition to a consultant role or something similar. I haven’t done a true consultant role before, so I’m not sure how or if I can handle it, but it feels like the right change at the right time. I earn the majority of our household income as well, so the risk is shared by my wife, who is very supportive.

    I’ve taken on some risk in my career, but I haven’t really challenged myself. I believe in myself, and I have the support around me. I’d like your support as well…invest in me and watch me soar.

  78. I have always taken risks, it seems like the safest thing to do. Although I graduated with a degree in Chemical Engineering I’ve been an actor, personal trainer, street performer and now I’m a professional magician and speaker – never an engineer! I walk the line between financial insecurity and personal realisation everyday – it risks what I have but not who I am.

    I recently launched a personal and business development course for magicians, only 4 people can attend each event and the focus is all on what I can share. It’s live and in person, there’s no where for me to hide.

    I have a well established reputation in the UK which brings with it expectations. As the day that I “open the doors” comes closer I’m feeling the fear of failure breathing down my neck………

  79. “To Risk”

    by William Arthur Ward

    To laugh is to risk appearing a fool,

    To weep is to risk appearing sentimental.

    To reach out to another is to risk involvement,

    To expose feelings is to risk exposing your true self.

    To place your ideas and dreams before a crowd is to risk their loss.

    To love is to risk not being loved in return,

    To live is to risk dying,

    To hope is to risk despair,

    To try is to risk failure.

    But risks must be taken because the greatest hazard in life is to risk nothing.

    The person who risks nothing, does nothing, has nothing, is nothing.

    He may avoid suffering and sorrow,

    But he cannot learn, feel, change, grow or live.

    Chained by his servitude he is a slave who has forfeited all freedom.

    Only a person who risks is free.

    The pessimist complains about the wind;

    The optimist expects it to change;

    And the realist adjusts the sails.

    I think that sums it up nicely.

    The crucial point that Ben and Reid make is the relationship between RISK and REWARD. Most people don’t take enough risk full stop but risk must be measured for reward or return otherwise the risk is foolish.

    I am taking a calculated risk to build my new business and hope that Reid and Ben take a measured RISK to find out what it’s about to see what REWARDS lie ahead for us all!


  80. Reading the start of your post concerning our genetic material being ill adapted to risk, something did bother me in this idea that natural selection shaped the human brain just to stay alive long enough to reproduce and raise offspring. This really bothered me because I am in the process of making a very big (probably the biggest) risk in my carrier.

    I’m also an evolutionary biologist and I know that the genomes (and consequently brains) of our cave ancestors are very much the same as modern humans. Are we therefore ill prepare to take risk ?

    I started to think why do we have such big brain after all ? really just to avoid risk ?

    To have big brain at a first place, the human baby needs to be born pre-term in order to pass the birth canal. Our very first step in life is an incredible risky journey that every mom and child is ready to take in order to provide the next generation of human with the unique capacity to think. We have such capacities not to avoid risk but on the contrary to take them : Thanks to the plasticity of the brain, human have colonized almost all the continents of this planets and adapted to most climates and challenges. Today, all the people on this planet are the descendants of these entrepreneurs that thousand of years ago took incredible risks.

    Does this matter at all in the subject of risk ? Well, if we believe that our genetic material is ill prepared to take risk then you taking a risk means that you will have to go against your own nature. That thought to me is rather depressing and fatalistic because we can’t really change what we are made of.

    But if we believe that risk is inherent to our very human nature, we are not only ready to take risk but also well adapted to the consequence of risk. Everyone have realized that, in stressful situations, we adapt and innovate much quicker. This feature is a robust program of our brain to adapt and not some sort of response that goes against our own nature. Knowing this distinction is key to be willing to take risk.

    Today I have quit my job as a associate professor in evolutionary biologist. I had a comfortable and successful job but now it is time for me to move onto something else : my goal is to move to Boston and start a new genomic company. I can go more into the details of this long process but I think what is more useful to known is what allowed me to take that risk and this is mainly two things :

    My success in my carrier (I’m leaving while I am at the top of my previous carrier)

    but also (and maybe more importantly) the conviction that taking risk is indeed hardwired in my genome.

  81. I think the real key here is to understand that comfort is the biggest resilience-killer. We tend to think of things in terms of “resource management”, and think that by working a high-paying job and not moving out of our parents’ house, we are saving resources that give us more options. Unfortunately, the world doesn’t quit work that way.

    This post actually reflects the paradox I’ve been dealing with for a while and the conclusion I eventually came to. I’ve always had big dreams, but in recent years the economic uncertainty of the world made me wonder whether it’s more important to seek job security and a lower economic footprint. It eventually hit me that there’s no paradox at all; the conventional route to “job security” is far more dangerous than the personal and economic risks of being an entrepreneur. Entrepreneurs may not save as much money or have a predictable stream of income, but for that same reason they’re constantly adapting.

    The more complex a world we live in, the more our safety relies on our ability to adapt; and we live in a much more complex world than ever before.

  82. Wow, a lot of comments. I’ll try to keep this brief. I’m 26 and currently an MS.MBA student (MS is in Information Systems.) Big fan of Ben’s, having read his book several years ago and his blog for a while now, too (even commented on a post a year or so ago defending higher education and exchanged an email or two with him.)

    Leading up to grad school, I was working on my own start-up, complete with a team of developers. I decided to go back to school to get a more structured education and perhaps more stable career path. I’m thinking of working once more on my start-up, but I’m afraid this will put to risk a nice, stable career path that I’ve set myself up for. Some help would be really appreciated.

    Thanks to Tim, Reid, and Ben for this post/offer.

  83. Hey Guys,

    It is redundant by this point, but thanks for the great post.

    I really enjoyed the dichotomy of humanity in the past to humanity today. I have always perceived this shift from body to mind in regards to the individuals concern. As outlined in the stories of humanity 15,000 years ago the concern of people was preservation of the body. Whether is was exterior threats or fulfilling the basic needs in life. Overtime and most prominently in todays society we are more concerned about the preservation of our minds.

    I think this can be attributed to something Daniel Pink wrote, which said we are in a world of abundance and automation. We no longer have to worry about the threat or lack of our basic needs. This brings me to the risk in my life. I have always been fascinated with the notion a healthy body, brings a healthy mind. Just as Richard Branson said, when you need to focus your mind, work out.

    Working in the finance sector in NYC is a tedious and repititive career that does no good for the mind or the body. I have been calculated in the risks taken up to this point, whether it be sabbaticals or seminars. These risks have allowed be to travel to 20+ countries and be exposed to cultures and all they have to offer. Between a mix of friends and family I have been presented a unique opportunity to try and expand and build health conscious drinks.

    Firstly, we have tested and experimented with a native peruvian liqour being infused with a mix of local superfruits. (Think Veev). This is expanding on a similar established product.

    Secondly, which I am much more excited about is, a proprietary blend of these superfruits used in a health drink. Something that is truly good for you, unlike products that claim to be “vitamins” and provide “life”. This is something that we hope to make availble to the general public.

    The risky part, is that capital needed to break into these industries in the States is quite high. I am aiming to move to Peru in the coming months to test the market and hopefully expand back to the US. This will require me to permanently leave my steady job, and also uproot myself culturally. Just as you said in the article I am justifying this overseas adventure as if I fail professionally, I will grow immensely on the personal side.

    I would love your help with a push on the professional aspects of this risky endeavor. If it doesn’t happen it is great to see the insighful responses and strides people are making to get to the life they imagined.



  84. Thanks for not only presenting the opportunity to discuss our personal career/risk stories, but also giving us the chance to help each other out by showing how many of us are in the same boat.


    I am in need of some major mentoring.

    I have been teaching in a private school for 8 years now, eighth grade English, and I am good at my job, I find teaching boys about literature and life VERY rewarding, and, my career path is stable. The school I work at is full of teachers and administrators who have been here for between 20-40 years.

    However, I am not happy. Because people stay here so long, there are very few opportunities for career advancement. Also, although I am trying something new almost ever time I get in front of a class, I am not challenged by my job and don’t find the work rewarding because of the mundane nature of subject teaching.

    I am in full blown pivot mode. I know I need to make a change, yet I have the very heavy risk of change weighing me down at times.

    My pay is not very good, which I have been told is not going to change. I have a growing family: two kids under 3, a great wife who is also an educator, and a mortgage that is probably more than we should be paying. For the financial stability of my family, I cannot stay in the same job, and I cannot quit and risk the instability of joblessness. Oh yeah, because we both work, we will have the double cost of day care to deal with in the fall.

    So, I have been trying to find a different path. I have discussed some entrepreneurship ideas with colleagues but they all seem to fade away. I have been trying to make connections at companies that seem like cool places to work in the Boston area, jobs in tech, marketing, sales, and education. However, I don’t have much experience outside of teaching. I do earn some nods and laughs when I have spoken to people in other fields and tell them that I have a great deal of experience in sales/marketing/product evangelism: I do it everyday, selling Shakespeare and having my customers come back wanting more, etc…

    I feel stuck. I am trying to break out of the rut I am in, (I am also trying to finish a thesis on Thomas Pynchon to earn my ALM degree from the Harvard Extension School), but I feel constantly thwarted by my lack of experience and the feelings that sometimes rise that I do have a good job (I know deep down that I don’t have the right job for me – at times my creativity and experimentation in the classroom have been penalized; ex. putting my desks in a discussion circle is not standard practice.) Another aspect tying me to my current job is the carrot that soon my kids could attend the school-which is a good school- for free…

    I have thought about creating my own job here, going to the headmaster with a job discription and everything. There are plenty of areas that need guidance and someone to run-yet I feel I am stuck and pigeonholed.

    Any help would be greatly appreciated!

  85. Hi there, I just moved from Canada to Spain and just started to work as a location-independent SEO Consultant. The risk is already taken since I’m now in Barcelona since a week and just starting to experience it.

    I would have define my move as a high risk a couple months ago but now I know the rewards will outweigh the things (including a job offer) I had to let down to do this move.

    I’m currently working on my new website branded as location-independent SEO consultant. Being mentored by Ben and Reid would be awesome 🙂


  86. The idea of risk is very insidious. If you give into risk (i.e. avoid it at all costs) then things that would not normally be seen as risky take on an aura of risk in ones mind.

    The thing that I would most like to change in the next 30-60 days is that I would like to get a new Internet based business started. I have read “The 4 Hour Work Week” several times and although I know in my heart that the ideas are sound, there is something in my head that has kept me from pursuing my dreams of total freedom.

    If I had to boil it down to one thing it would be the idea of risk. I keep having questions like:

    What kind of business would be the best for me to start?

    What if I put a lot of time into an idea and it fails?

    Can I really make money doing something like this?

    I think I have become so risk averse that I see everything other than my current norm as a risk. I would love to be able to break out of this self perpetuating hell I have stumbled into. It would be great to have someone to help nudge me in the right direction and get me started. Having someone with experience to guide me through the start up phase and get me moving in the right direction would be great..

    I really enjoyed this article. Thank you for the great information!!!


    James Schaum

  87. Hello,

    Thank you for this inspiring post. My name is Michelle, I live in NYC, I have three children. The oldest is 6 and my youngest is 5 months. My middle son has cerebellar hypoplasia/cerebral palsy and he is just amazing. I’ve worked at my existing company for over 11 years now. The company is amazing. It’s been so comfortable that I’ve made it impossible to take risks. A few months ago our good friends in Cali presented my husband and I with a great opportunity to move to Cali (something we’ve always wanted to do) to run a baby store and it’s website. We were so excited, but after seeing the financials we quickly retreated back to the safety of our 9-5 jobs. After returning to work from maternity leave, I made a request to go part time so I can spend more time with my children and focus on alternative therapies for my son. The request was granted, I would be part time with all benefits. The day before I was to start my new schedule I was told by my boss that they decided to change the offer, I would lose all benefits and would be a 1099 instead. We thought about it and decided maybe it was not the right time to go part time since we needed the benefits. Pretty much our fears has gotten the best of us. Later in the week, I had lunch with a good friend of mine who introduced me to Stuart Wilde’s teachings specifically The Mastery of Money seminar that is on youtube. He presents things in a really interesting way and his words deeply resonated with me. I bought all his audio books, meditations and kindle books shortly after. I started to practice meditations, affirmations and kept an eye out for signs of what I really want to do.

    One afternoon, I was in the children’s section of the library with my children and there was a book called Get Rich Click by Marc Ostrofsky. I just glanced at the book thinking what is this book doing in the children’s section. I finally picked it up after ignoring it for a half hour. This was just what I needed, I read the book and thought about the baby business once again and started to really see myself running a shop and website. I reached out to the guy and he was still interested in selling it. I devised an action plan to convince our future partners and my husband to go for it, I stirred a lot of excitement. This is still the beginning stages and we are working on negotiating on the price of the business. I’m a huge Seth Godin fan and I feel I can implement the principles he writes about into this business and use the tools from Tim’s 4hww book and some of Ramit Sethi’s strategies. I do feel we will be successful with the boat loads of great knowledge I’ve already received from these amazing writers but if I am granted this mentoring opportunity it would be the cherry of all cherries, the gravy of a gravies. Thanks for the opportunity and the Michelle before the Stuart Wilde books would’ve never left this comment. So I thank you Stuart for your words and my actions.

  88. Thank you Tim, Reid, and Ben for collaborating on this spectacular post! Double-thanks for this awesome opportunity!

    At the moment, I have my own graphic design company. Not making a whole lot of money, but for now it’s paying the bills. My older brother, Mark, is a Sales/Finance Manager at a car dealership. He is GREAT at what he does, and has gotten ” the art of the sale” down to a science. We recently decided that with all of his experience, expertise, and a passionate desire to share these techniques and strategies with others, that we should create a seminar for people to attend and learn. Now, we are developing lesson-plans for the event, dvds, audio, and other materials to serve our niche of sales professionals.

    Sidebar: I stopped by Mark’s job last week and before leaving I overheard something that I believe I was meant to hear. It was my brother’s boss. In a brusque tone he scolded Mark with these words that I will never forget; “Listen, I don’t work for you, you work for me. It’s my way or the highway.” This sparked in me a new passion to help get my brother’s training/seminar off the ground. He is too smart and talented to be subject to that crap! Any advice would be greatly appreciated! Thanks again!

  89. After failing in a previous start-up, I’m on plan B and having gotten back on my feet financially, I’m pursuing plan – A, and volunteering at a start-up robotics company one day a week, so no-pay/high learning. Along with that I’m reaching out to the local robotics community and other entrepreneurs to gage interest on a robotics start-up.

    Is this really risk? I’m only gambling with my time and in reality networking and just setting up a safety net for my next potential job.

  90. Hi, my name is Rose and I’m quickly approaching my thirties. As a Gen-Y, I sometimes look at where I’m at in my career and wonder why I’m not farther. Then I remember that I have been learning as I go, on the job and through my own learning and development for the past 6 years. I have built and managed HR departments for two small companies in very different industries and when I think about how I got to where I am in my career, I have to be proud because I did it on my own – though I received guidance from mentors when I found myself in unfamiliar territory.

    Still, as a Gen-Y or simply as an ambitious person, I’m always looking ahead for more.

    In next 30-60 days I want to see myself in a start-up, this time in the tech industry up in the bay area. I want to surround myself with innovative thinkers and people who have a vested interest in the company that they are in. I want to work together and help create an innovative, motivated and FUN environment where ideas flow easily and nothing is out of the question. Basically, I want to help create/contribute to the environment that makes people excited and happy to come to work.

    My risk in this move would be a physical move from the people and place that I have been for the past 14 years. I would be leaving behind my network and mentors and going to a place where the only security net I have would be that flights home aren’t too expensive. It’s funny, as I’m writing this the feeling of anxiety far outweighs my actual reasons to fear all of this risk. I have a plan A and a plan B. Plan Z would be to move back and call the whole things a learning experience if it didn’t work out.

    I admire those people who have a goal in mind and go for it without worrying about many of the details. Hitting the reset button (or the fast forward button) on your life and jumping into something that has more pros than cons, more reward than risk, it should be a no brainer. We just have to let go of our fear of failure and the discomfort of change. Financially I can do this, even if I ended up moving back home after a year. Leaving people behind, that’s what makes me hesitate, but there is little risk in losing people.

  91. For over 10 years, my life was dictated by a steady job; by expectations put on me by school, my family and, of course, myself. At first, it was fulfilling and satisfying. I achieved goals and made things happen! I was streaking to my goal very quickly and couldn’t wait to arrive!

    Then I did. I made it to that place where “all of my career aspirations would miraculously come together and offer me up this extremely rewarding and ever-fulfilling work environment and how could I ever want more”? Once I was there, though, all I felt was drained and detached and disinterested.

    What now? I had spent so much energy and so much time focused on this one goal and now I didn’t even like being there? What was wrong with me? How ungrateful I was to myself and why couldn’t I just appreciate the achievement I had, well, achieved?!

    Over the next few years, I floundered with no goal. Being a person who needs something to reach for, who had always had somewhere to “go”, I felt vulnerable and confused.

    Then, this past year, I was employed at a small company with a scrappy startup attitude (even though they were quite well established) that was bursting with raw potential. My goals there were lofty and ambitious and I felt like I was back! Here is my inspiration! Let’s take this place to the next level, I screeched! The problem was, that next level was my vision for the company, not the owners’ vision for the company. This “inspiration” I had found, was mine alone, I was forced to recognize.

    Once I admitted this, a few things happened. I realized in order to truly find fulfillment, I had to invest in me. I had to stop looking at a full time corporate job as the goal, as it was obviously not fulfilling my needs. But I had to be calculating and decisive and make an intelligent decision that wouldn’t put in me economic ruin.

    That’s when I looked around me and saw all of these inexperienced but ultra-talented and “hungry” co-workers. That’s when I started to see them as part of my calculated exit and my next goal.

    I do need to say at this point that I am not risk-averse. I have taken many risks in my life, but when it came to my career, I always took the route I “should” take.

    One day, I woke up and decided I was going to take the road everyone was telling me lead to certain disaster. I was going to quit my full time “stable” job and go out on my own–with no promises of success and no real leads to any sort of real work–with only an idea. I thought the hardest part was going to be walking out the door on my job. Turns out, the hardest part is now– everyday overcoming my negativity bias and convincing myself that this will work out.

    Because it has to. I’m more fulfilled now than I’ve ever been.

  92. Over the past two months, I’ve been looking to transition out of my current career (Accounting) into public speaking. I’m highly passionate about homelessness, and even slept outside on my school campus for 5 Days (raising $15,000) to garner awareness for homelessness in youth. I’m not quite sure how to break into the public speaking industry, though.

    I see this as a risk, but not one that I can’t overcome. I have been cold-calling some of my favourite public speakers lately, and have had great success in getting in touch with them and talking about how they broke into the industry etc. What I see as my major barrier right now is an opportunity to demonstrate my speaking abilities in front of a credible audience, so I am currently devising a way to make that happen.

    – Jordan

  93. I’m 27 with an MBA degree and working and studying to earn my CFA charter. I’ve been married for almost a year to an amazing woman and looking to start having a couple kids soon.

    – The change that I want to make in my career in the next couple months is to find a new opportunity in the finance field. My current position is very administrative and bureaucratic. I want to be able to apply some creativity in my work and enjoy a little more freedom to make decisions on my own. I find portfolio management and research very interesting which is why I decided to go through the CFA program. While I believe education is important it is nothing without experiences to apply it to which is why I’m looking for a new opportunity to gain the type of career experience I want.

    – Honestly, I do have negativity bias in my thinking towards this goal. For example, the finance industry is flooded with talented people from Ivy League schools and having not graduated from one I realize that I have to do that much more to be noticed. After reading The Four Hour Work Week and having this article reinforce that mentality, seeing that the worse case scenario is survivable in most cases shows that it is not something I should feel afraid of. I am prepared to take risks that are beneficial to me in the long-term not just for my career but my life as a whole.

  94. In the next 30 days I plan to approach a global corporation, Linkedin to be exact, with a concept that many feel can help leverage their business to an entirely new level, take market share away from others giants in the social media landscape, as well as change the way people network for business locally and globally.

    There are people who think I might be insane for what I’m doing, but I personally don’t feel that we get anywhere in life by keeping our ideas to ourselves, or by approaching partnerships with a greedy mindset. I want to share my idea because there is a need right now that isn’t being filled and a company out there that can fill the hole. My theory is, why not work with the best and brightest in the industry?

    At this stage, I have developed a PowerPoint deck that clearly explains the concept. Additionally, I have been creating my team, including strategic alliances. I know it’s risky to approach a company that can take your idea and squash you in a hot second, but I also know that sometimes the risk is worth the reward.

    Honestly, I would just like to see this idea executed and mainly ensure that I’m protected legally. However, I differ from most people in the digital IP sector in that I don’t feel I should create a standalone venture in hopes of being purchased some day. I know who I created this for, and I would just like the opportunity to prove that it can work.

  95. I was a family physician for 12 years and became burnt out of being the rope tugged on by the insurance industry on one end, and government unrealistic expectations and requirements on the other. I was getting home later and later to try to make ends meet and becoming overly frustrated. After reading the 4 hour Work Week, I decided I did not want to spend the remaining 25 years of my work life suffering in an industry that had no solid direction or vision. I sat down and wrote out the idealized life for myself and my wife and kids. I still wanted to practice medicine because I love it, but under my own terms, and lifestyle. I discovered the world of Varicose Vein disease treatments. No residency exists for this specialty. I essentially cut my pay to 1/3 of what I was making so that I could work part time in family medicine while train with a doctor already experienced in vein treatments. I worked for free for this doctor and in return, saw patients for her which allowed her to make more money without paying me. After 3 years, I’ve switched my career to varicose vein disease treatment. I only work 4 days a week. No weekends, no holidays, no night call, and take 5 weeks vacation. I make 4 times more money than I did in my best year as a family doctor because I discovered a growing niche industry with few qualified providers. I’m so much happier, I could cry, and laugh. What I’d like to do now is continue the momentum by creating a passive income that requires less of my participation so I can travel more with my family. I’m interested in finding ways to use my experience to market something in the field of varicose veins that allows me to earn money without being present. Thanks for reading! — Brent

  96. Hi guys,

    I am an iPhone Developer from Pune,India. I have been through the concept of “LOW PAY HIGH LEARNING” thing and I have to tell you that it feels incredible even if you are paid less. We get a lot of knowledge which helps you survive and speak up when in need. Sometimes people even rely upon your judgements.I want to tell you that I was really happy when the post said “Take the risks that other people dont tend to” because (honestly) I used to bunk my college lectures for 2 main reasons :

    1. I didn’t understand a single word that was taught in college.

    2. Other students attended it even if they did not understand anything that was taught.

    But did my engineering with average grades(which is ok for me).Further, the difference between the Resilient and Fragile Careers. I believe I want to be stronger for which I would like to have a career like that of the real estate agent rather than that of a salaried employee. The overall post tells us to live better and to be stronger in our entire life, I guess. Would love to hear more from you guys.Will keep me motivated.Thanks

    –Parag Dulam

  97. Hi- Here are my answers to why I should win this contest –

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

    I have been offered a part-time consulting position in San Francisco -I’d be commuting from San Diego, yes every week, hopping on a plane Tuesday morning and flying back Thursday evening to be with my family. This would be a chance to grow an organization that is forward thinking (the organization cares for the elderly in a more humane way than other models). Hey- we are all going to get old some time, and we as a society better use our business skills to develop some place that we’d want to stay when we get old – right? . I’d get to apply and grow my business skill muscle and help the world be a better place at the same time. The mentoring would benefit not only me but all the families and others involved in the organization – it will have a large scale impact.

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

    It will be exciting and a great growth experience. Commuting will be hard at times but I have friends in start ups in San Fran -lots of energy and enthusiasm for new concepts and ideas.

  98. To add to my above comment – in my coaching sessions with Reid- I’d love help connecting to the best companies in which to present ‘Brown Bag Lunch’ seminars on Insights into dealing with Aging Parents and similar topics. Also, brainstorming on how to develop socially responsible profit centers – win-win.


  99. Reid/ Ben/ Tim,

    As succinct as possible/ cliff-notes version:

    What change do you want to make in the next 30 – 60 days?

    – Implement a strategy to exit my current job by generating income ‘on the side’ (sales consulting, contract work, app dev, etc.). Potentially finding a different job that excites me in the process.

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

    – I have a wife and kids, I’m the sole bread winner and have been for nearly 15 yrs – my risk is becomes theirs too.

    – Without a college degree or formal training I have climbed the ranks within a sales organization over the last 10 years and now hold a senior leadership role. I feel like I painted myself into a corner, one company, one industry and now have all the expenses of a ‘successful’ career man (mortgage, cars, pets, vacations that my family attends without me). I want to own my own business or earn money doing things that I enjoy but I can’t afford to take the financial hit (I could handle it, but my family has grown to enjoy the life they have today).

    – I can’t play the corporate game for another 30-40 years, I’ve missed too much of my kids’ lives already.

    – I have skills and talents that are underutilized in my current environment and I have very little free time/ resource to invest in entrepreneurial ventures that inspire me and others, although I have taken a few swings at things.

    Thanks so much, I hope I get the chance to connect.


  100. Risks are only bad if you are afraid of them. They key to true success is mastering your will. If you have mastered your will, then you can approach ‘risk’ with no fear and with complete confidence in your ability to handle the situation no matter the outcome. With this will power in hand, a ‘risk’ ceases to be risky, but simply an opportunity. Your will power allows you to tame the wolf and have impeccable judegement about the river. Should you still fail, your will allows you to fight the wolf, or swim like hell. Either way, you have mastered yourself and your interactions with the world, allowing yourself to get the most out of every experience until the end.