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

climb at your own risk

(Photo by graziedavvero)

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

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

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

Enter Ben and Reid

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

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

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

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

The world has changed, but our brains have not

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

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

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

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

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

What kinds of career risks should you take?

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

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

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

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

Jobs that pay less in cash but offer tremendous learning.

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

– Internships

– Apprenticeships

– High-level assistantships

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

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

– Freelance writing

– Programming

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

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

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

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

An opportunity where the risks are highly publicized.

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

– Starting a company

– Working in a high tech industry

Overseas adventures.

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

– Foreign assignment within your company

– Attending a conference or seminar in another country

– Volunteering overseas

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

How often should you be taking risks?

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

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

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

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

– Business

– Entertainment

– Sales

Non-risky careers (less severe shocks) included:

– Education

– Health care

– Engineering

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

But it’s exactly the opposite.

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

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

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

Fragile careers vs. Resilient careers

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

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

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

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

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

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

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

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

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

What will be your unmatched growth experience?

Final thoughts from Reid

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

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

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

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

[On one other risk that paid off]

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

4 keys to becoming a more resilient, intelligent risk taker

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

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

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

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

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

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

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

Here’s what we can offer:

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

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

– Your story will be highlighted in our LinkedIn Group.

– Free Linkedin Premium subscription

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


Odds and Ends: App Contest Winner

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

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

Our top two favorite runner-ups:

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

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

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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

  1. I’ve taken risks from a very early age and have been greatly rewarded for doing so. I dropped out of college (a tech degree) 15 years ago to pursue a career in music, moved to NYC without money or contacts and these two risks proved to be the best decisions of my life. I’m a Grammy nominated musician. I’ve scored TV shows, films, commercials. Music has allowed me to see the world and live a life that resembles an adventure.

    Problem is, I never quite got the tech bug out of my system. So I plan on taking a risk to try to expand what I do. I plan on going back to school to get a new degree and experience in the tech world, maybe coding, maybe designing, maybe managing, who knows. And I plan to combine the insights I get with the experience in the entertainment industry I have, to create technologies that will contribute back to the industry that has given me so much. In particular, I’d love to try to put art and education front and center and to counter what you so rightly refer to as low-volatility in the short term. Everybody wants to find a short cut to this low volatility when in reality that is just a mirage. Just look at what this mentality has done for the music industry in the US, where it’s all flavor of the month instead of long term career development.

    I also firmly believe in the positive impact that art in its many forms has to enlighten and inform our society. We need more of the insightful commentary that art provides on our daily life rather than simply another empty app designed to make millions.

    I routinely say that I think certainty is not such a good thing. It closes you to experimentation, mistakes and growth. I am not certain of where these new risks will lead to and that is exactly how it should be.

  2. Hey there. I’m Jonathan and fell on this article while I haven’t been on Tim’s site for a while. Its funny because this article coincides with what I’m currently doing. I’m taking risks in a new yet at the same token a somewhat familiar field. While doing so, in a month the staff culture has improved, the level of product has improved immensely, and the owners are fighting to pull me away from my other endeavors. I’m striving to be one of the most recognizable Trainers, Coaches, and Even possibly competitors in the world. I’ve already been called the Filipino Freddie Roach and Apollo Creed by my clients. Exciting, scary, and fun!

  3. I’m a designer in Atlanta looking to grow and learn and not give up on having real career mentors. I’m on the verge of getting engaged. I still rent – my goal is to make it out to SF and learn from the best in the design industry. I’m still working in my first real gig out of school, for a marketing/design firm that deals with education and non-profit. The work we do is based mainly in print and conceptual ideas. It’s rewarding on some levels and stuck in the past on others. I am eager to take on more and learn more about digital and grow. I’m in the situation where the work we do here isn’t evolving with the times, and my boss is a micro-manager who constantly gets in his own way and, ultimately, in the way of the company itself. I took this job wanting a mentor from whom to learn, and he’s become less and less that as he’s let the business devolve into a mash-up of irrelevance being salved with sort of business alternative medicines, like “tribe meetings” and “personal development plans.” Kind of kooky. It’s a small firm (6-8) people, and the workload doesn’t permit much experimentation within the confines. I’m at the place where I want to quit, having been here for so long with little opportunity for advancement without leaving, but I’m not financially ready to just drop this job. I read your post and really felt the pangs of life-adventure and risk that are constantly quelled by the supposed stability of having a full-time position within my company. I have connections in SF, but its tough to door-to-door a portfolio while living 3000 miles away. It also hard to make too much noise around the Atlanta area without it getting back to my current boss who is well-connected in the industry. I’m really trying to figure out the best way to get my foot in the door with a respected one or few modern design agencies while also navigating the course of life events, day to day and long-term, that have to be handled. I’d be grateful for your help…

  4. I was reflecting on what I wanted my “theme” for 2012 to be and I came up with a very similar idea to what’s mentioned here. I call it “eurisk”. Just as psychologists parse out stress into “eustress” (good stress– like the kind that makes you do well in your performance) and “distress” (bad stress– like the kind when your parents get divorced), I want to do the same for risk.

    So there’s bad risk (the risk of something awful happening) and good risk– “eurisk” (the risk of something awesome happening).

    My goal this year is to ask myself “What would have a small chance of paying off many times over the effort I put into it?” I figure if I can do those things as much as possible, then that will ultimately be a huge win. The trick is to ignore the costs, because if I take many of these risks, the costs will easily be justified.

    What has a POTENTIALLY UNBOUNDED UPSIDE? Those are the things I want to do.

    * Go to parties– meeting people CAN be awesome, but sometimes it’s just a boring evening where you don’t connect with anyone… but meeting one cool friend for life is worth a few boring parties

    * Invest in my passions– I need to spend slightly uncomfortable amounts of money on risky things I’m passionate about. Example: when starting my blog (see the link on my name), I knew I wanted a really nice logo, but it cost a few hundred dollars, and I remember thinking “maybe I won’t go through with it”. But I’m sure enough that this blog is an important, door-opening opportunity that I said “Eurisk!” and did it. Every time I have to spend more money than I want, I ask “does this have a potentially unbounded upside?”

    * Contact my heroes– When I hear about people who have done awesome and inspiring things, why don’t I rise above the 99% of people who think “they’d never respond!” and instead try and seek them out. I now get regular mentorship from a well-respected entrepreneur because I asked.

    So far this has been awesome, but I know my career is a place where I could apply this philosophy even more.

  5. I have been in the information technology sector for over 24 years as a developer, administrator, consultant, manager, director, project manager. I have worked for several major companies and ran my own successful business for several years. I sold that business just before the dot-com bust in the early 2000’s.

    I was laid off from my cushy corporate job back in September of 2011. I immediately took another corporate position to protect my income. Within weeks I realized my business ethics were being compromised if I stayed. I took a risk and left in December of 2011.

    I took a risk. It was better to be unemployed than to have my professional reputation ruined. I immediately started networking for some contract work with firms in the region. I started doing some low end work for one in March but it offered some great potential upside – exposure to senior management. Once they saw what I was capable of, they might opt to bring me in at a higher level. I am still pursuing that end but they are slow to make decisions and I need some ideas to spark them to a close.

    I reached out to another company for a full time opportunity but after we chatted initially, the position was not what I was looking for. The company offered a lot of potential so I discussed with them the thought of altering the position a good deal. They liked the idea and pitched it to the investors. The investors agreed with the idea but they were not ready to do it yet. When they reached out to tell me that it would have to wait due to other directions they wanted to pursue for a few months, I offered to consult with them on a regular basis to start laying the ground work for when they wanted to open up the new position we discussed.

    They agreed to do this but we have to close it yet. The work will start soon most likely. I need to keep the momentum going and turn the thought into an agreement and contract to get it going. The contract is not lucrative but the long term benefit is. There is exposure to management at all levels and to all aspects of the company. Essentially the position is a director of an entire division that focuses on IT services for clients. They want to grow this division and have it meld better with their other lines of business. They have my business plan in their hands for this growth. I did this work for free to show them my interest and desire.

    I just have to keep their interest and close either of these opportunities. Both are very interesting, even if only ever contract positions.

  6. I have just moved to Costa Rica ( 7th country in the last 10 years). For the first 5 moves I worked on internships, sustainability NGOs and multinationals. On my Last move (Colombia) I set up two companies (both service focused -with a MASSIVE limitation for growth)…ironically, my specialty was helping other people set up their own businesses abroad.

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

    I sick of dry, monotonous work, and craving something exciting and challenging – I am starting a company on one of two things I love: Yoga-lifestyle & Jewelry. (still dry testing but have a feeling it will be the first grwoing onto the second)

    Heres the catch: I have very littlee idea on how to implement the business model I want to work with…. (-i will tel you more about it on that 30 minute call).

    Im trying to simplify what in my head is the next distribution scheme in Latin America… and how to automatize a system for an unexperienced but eager sales team of just-over-18 girls. . .

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

    1. I have very little idea what im doing (but learning and adapting increadibly fast and have a clear idea of what I want to get to.)

    2. It will take a reasonably large investment , which I am not prepared to loose so easily.

    3. If this doesnt work I have to get a job. And I really don´t want to – so any advice to minimize the risk failure is much appreciated.

  7. Hey everyone,

    My name is Brad de Comarmond. My story goes like this:

    I grew up with old fashioned parents that both worked (and still work) dead end 9-5’s and never took risks or followed their passions. They always made excuses why they didn’t invest or take chances. Most of them were because they wanted to ensure me a stable upbringing which I can admire. Being from South Africa and without college degrees, my parents took the first jobs they could land back in 1991 and are still there today. (pretty depressing to say the least). After spending my whole childhood and the beginning of my adulthood watching my parents live mundane and unfulfilled lives, I vowed to never be like them in a career sense. I knew I could never do something I didn’t enjoy.

    Being a entrepreneur at heart (and a Jew), I always looked for ways to make money on my own without having to wear a silk noose and get fat on an office chair.

    Fortunately, a few years ago, I had the opportunity to intern with a husband of wife in South Tampa that essentially retired in their mid 30’s from real estate investing and other ventures. After learning a ton from them (including being introduced to 4HWW from them), I decided to follow their steps in real estate.

    My first big risk was borrowing $200,000 for a family member to buy, rehab, and sell houses in one of the toughest economic markets in America (Tampa). After almost a year, we have learned some very tough lessons about unexpected costs, who to trust, and the need to persevere. Fortunately, we have managed to stay afloat and make some money. With this business model set up, I am ready to move to my next risk.

    For a few years, I have been modeling part time when the opportunity presents itself in Tampa and Orlando but its not big enough of a market to pay the bills. Without knowing anyone in Miami, I found a roommate online and will be moving there at the end of July in hopes of modeling full time.

    I’m not sure what to expect. Hopefully all will work out, but I do know one thing.

    I’ve lived with regret before in my life and I have seen regret on my parents’ faces since I was 4 years old. When I look over my life from my deathbed when I’m old, I don’t ever want to say “I wonder what would have happened if I took that risk…” I want to say ” I lived my life to the fullest because I wasn’t afraid to fail while chasing a fulfilling life.”

  8. I feel as though I have been living the past year in a state of risk. In April 2011 I was laid off from my corporate job in product development for a food manufacturing company. Knowing the economy of the area I decided to take the opportunity to travel and live in another country. I went to Italy to WWOOF and live on organic farms. I thrust myself into the homes of strangers and came back to Portland, OR with a greater appreciation of food and what it takes to get that food to my plate. I have since devoted my job search to more sustainable food opportunities and have had a hard time finding the jobs that I want to do. I worry that I wont find the opportunity to thrive in but feel the risk of holding out for the job that will make a lasting impression on myself and to those I come in contact with holds a greater outcome for me.

    You mentioned working for little money and I am currently doing just that. I started out staging in a bakery of a James Beard award bakebook author and after a few weeks time was offered a part time position. This opportunity does not pay well at all but I am learning the inside day to day of what it takes to run a small business of this kind and have the opportunity to fine tune my baking skills with someone that has been recognized nationally.

    In the next 45-60 days I would like to be working meaningfully within farm-to school, be involved in local food hub creation, a voice in the upcoming farm bill or anything food related that will help steer the direction of our country and the way we treat food and ourselves. I have devoted my time since being back in the states to searching out opportunities that will land me where I want to be. My time is running out as I have those student loans that will ultimately decide how much money I have to make but I am willing to risk this time in search of what will make the most difference for all of us later on.

  9. At 42 and after 19 years with one tv station, my significant Dean Kendrick of San Francisco is convicted to risk saying “no more” to working for business models obsessed with “death, destruction, devastation and outing others unfavorably.”

    His goal: He is determined to focus his camera on “fun, frivolity, food, fantasy, futuristic ideas, culture, fancifulness”. His creativity is what drives him, but his history as a technician makes him a one man show in short, long and interactive media formats. He is a master.

    He is considered the best handheld cameraman in the Bay Area for his expertise and his personality…. I don’t want to see him be a flash in the pan, media is brutal. As an entrepreneur myself (, I am completely behind him but this is his dream, and his coaching opportunity.

    I have been a fan, client, reader of Tim Ferris and friends for the last ten years…. Dean Kendrick has the a lot to offer the community as he gets to know our lifestyle first hand.


    Jennifer Choate


  10. Hey, how’s it going everyone. I’m Kristina.

    I’m a Media Manager in New York. The opportunity for the role first appeared because of a freelance writing gig I did for about three years, which rolled into two partners leaving the old firm and asking to take me with them.

    It sounds scary, but after three years of working with them, I established a very nontraditional routine that I was able to roll over to my new role. I was able to keep my freelance schedule (which only has me in the office 3 days a week–plenty of time for Muay Thai!), I wear what I want and I negotiated a higher rate and a competitive bonus structure.

    The exchange was that I was, once-again, employed “by someone” and I had to learn a plethora of new skills, which over time allows me to be more valuable for future endeavors.

    I suppose what I’d like to do in the next 30-60 days is learn how to utilize the obvious savvy that I have buried somewhere within me, and translate that into my entrepreneurial, artistic side. I left the Corporate world to “work on my own terms”, but I’ve only completed about 50% of that journey: I know what my terms are, but I don’t know WHO or HOW to demand them of.

    The risks are endless… If I launch a successful, creative business venture that’s lucrative and more meaningful than the work I’m currently doing for someone else, I’ll have to sacrifice those relationships and that comfort for the unknown. But I also KNOW that the same way we were built to mitigate natural risks, we were also built to create. We were built to explore, to be adventurous. I mean, that’s gotta be the reason why our hearts beat so hard when we try something new but we don’t die, right?

  11. My name is Mac Senour. For the last 30 years I have made video games for other people. When I say “made”, I am a Producer. I am responsible for the look, feel, timeliness and budget. That also means although I do not program, or draw art or design the game, I am responsible for all of it.

    Over that 30 years I have made millions, for other people or companies. I know for a fact that my work has led to three people’s early retirement. Meanwhile, I was paid a nice wage. More than enough to live on, but not in the “retire now” range.

    Over the years I have been told several times: “Just quit and go it alone”, but that’s not reasonable unless you have a team around who also quit. I’ve never been in that situation.

    I was recently let go by MTV. I think it’s my time again, and I don’t want to miss the opportunity.

    I have a game design ready.

    I am thinking of going to Kickstarter for the money.

    I have a team ready, but they want to be paid.

    I just need some mentoring.

    Thank you for reading this.

    1. I was going to write my story until I read about Mac here. I really hope you pick him. Good luck to everybody pouring their hearts out! Both in this contest, but also with their situations and risks.

      Read a cool card the other day: “Everything will be ok in the end. If it’s not ok? It’s not the end.” Reminded me that every crossroad I’ve encountered just gives me a new horizon to sail into.

  12. What do you do when your whole life is spent learning how to kill efficiently?

    I am a Cavalry Officer in the United States Army, teaching history at West Point. And I recently realized that I am “caught” by the giant trap that is government service.

    The U.S. Army has a retirement system which guarantees you half of your salary for the rest of your life once you have served 20 years. This is actually a legacy that dates all the way back to the days of Rome, where Soldiers of the Empire were given a farm after 20 years of service in the Legion.

    The problem today (for the Army’s retirement system) is that most Soldiers end up living almost 40 years after they retire. And having 12 years of active service, going on 13, I realized that I was “trapped” by the security of this retirement system. Everyone I spoke to advised me that it would be crazy to give this up. Just gut it out, they say. Serve 7 more years.

    But for me, I realized that I was trapped. I guess it was after I read Tim Ferriss’s Four Hour Work Week when it came out, which inspired me to start my own company while in the Army. The New York Tour industry is not the greatest business for upside potential, and it requires way too much maintenance. So I gave that business over to a partner to manage, and decided to work on the website.

    Now, I have discovered website building and internet marketing as a passion, and since I don’t yet have anything of my own I want to market (Because I such a perfectionist), I am helping other people do theirs. Specifically, I have taken up Triathlons, and I have decided to start marketing the best coaches, bike fitters, energy supplements, and anything else that I believe in that also relates to the sport, and interests me.

    I have made the “Crazy” decision to leave the U.S. Army, leaving the retirement on the table. However, I have buffetted this a bit by staying in as a Reserve Officer writing books for the Center for Military History, telling the story of what we (The U.S. Army) did in Iraq, which is something I will be passionate about doing,

    So for me, while this is scary, and a huge step away from a life that has consumed me for the past 17 years (out of 34 on earth), I now realize I have to do it. I can make another pension anywhere, but I will never be able to get this time back, in my thirties, where men finally start to figure things out, where I am at my peak physical health, and I have enough time to start down a new path that will fulfill me.

    So this post is something that inspired me even before I read it, because it was this line of thinking that inspired me to finally take the “risk” and start living a brand new, exciting life.

  13. In less than two weeks, I’ll officially be launching my side business.

    Using the principles I learned in the 4HWW, I have a plan to automate all the time consuming parts I can train someone else to do, so I can focus on spending time with my clients, until I can train someone to do that part, too! We’ve tested each part of the system on a small scale and have seen promising results.

    Here’s the wrench: It’s a big risk for me because I’m also at the same time looking at a huge career opportunity at one of the “big social” website companies i near San Fransisco, CA.

    Do I take the dive and see where my business goes? Or do I play it “safe” and invest all my energy being one of many devs in a large (but very reputable) company that could set my career?

    Both involve big change, lots of passion, and energy. I’ve done a lot on my own so far without the privilege of a mentor to help me see the big picture. I’d love to share my ideas and learn from the experience of someone who’s already been there on both sides of this fence.

    When faced with the prospect of being employed by an influential tech company, or branching out on your own to try a new idea with promise? Which would it be?

    “There is No Box, only the limitations you set for yourself.”

  14. After reading the Four Hour Work Week two years ago I have set out on a journey to build a business that would allow me the freedom to do what I wanted, more importantly what I could do for others through my more available time. I always have found comfort in knowing that I am resilient when change does come and the voice in my head may say yes this is scary but I always know if will be fine.

    Things always workout no matter what, for me the uncertainty may be addictive in some ways maybe more of an unconscionable attitude but I love the thrill and knowing that its just me who I have to be responsible for and no one else. Yes it may be tough but I know the personal and professional development that comes with this new found resilience will set me apart from my peers. Its not always easy or fun or flashy or cool, but in the end its always worth it.

    In the next 60 days I intent to open two business that I have been working on for the past couple of months. I’m not sure what the future holds for them but I know it WILL WORK, and the reason I know? Its because I believe in my ability and the benefit it will be to my team and clients that it will effect and for that I’m truly grateful to God and the universe for giving me the ability to trust myself and have a creative mind.

    These two new business will be a huge benefit, although scary and not knowing all the details, I know how it will change my life and the lives that it effects in return. I’ve never actually started a business from the ground up and made it a functioning and working machine, but I cant wait to see it! I’m so excited… thank you to Tim and all his associates for giving me the momentum and the GO juice to pursue the life I deserve and not live a life of desperation and always wondering…. “What if”….

  15. I feel like this post was written for me. Thank you all for writing it, very comforting to hear at this time.

    My name is Richard Hanley Jr., I’m a father of two, married, and live with my parents.

    My 9-5 is an art director for an ad agency, but my 5-9 is an entrepreneur who thinks big and burns the midnight oil developing ideas.

    I have never spoken of this openly, but I am quitting my day job in September to work on my dreams 100%. The last 27 years have my life haven’t worked so its time to make a change. Start a new chapter on my book.

    I know my family and I won’t starve, I’ll freelance or cut grass if I have too to make ends meeet. But I will not work for anyone else. I can only get to where I want to go by investing into mysleft and I’m never going to know it unless I try.

    This article was just what I need to read, this best this year. And that’s hard to beat.



  16. I love reading posts like this one as it reminds me I’m on the right path and need to keep pushing my limits.

    I’m 21 and for the last 2-3 years I’ve been taking leaps and risks as I kept reading – and re-reading The Four Hour Work Week, The Education of Millionaires, Never Eat Alone and more… Much more.

    I’ve travelled, absorbed loads of online courses, taken internships, contacting successfull people, volonteered and tried pretty much anything and everything in order to get a foot in the door of the marketing world – even though I’m ”degree-free”.

    Within a couple months, I started seeing results – first getting a promotion at work, then a first personnal client, and it just kept comming.

    I was often incredibly lucky, scoring oppotunities I was totally unprepared for and then have to spend my nights learning the job I’d be doing the next day.

    Six months ago, I nailed a job interview and have been preparing a 2 year long – and 400 000$ budget – marketing campaing for the city I live in to attract new citizens from nearby citys. (3 days a week)

    To be totally honest, I’m underpaid (15$/h). However, I get to deal with major media, video production, web design companies and more. Also, I get to work with major influencer in education, entrepreneurship and social organisms AND the building I work in rents space for start ups, which lead me to find additionnal clients.

    The kicker, last week I got a second job for a video production company in which I’m in charge of doing their marketing but also providing strategies for to clients to get their videos in front of as many targeted eye-balls as possible.


    – I believe right now I need to focus on what I have secured, do my job well and keep learning for the next two years after what I’ll be able to take on bigger challenges and responsabilities, what are your thoughts about that?

    – Even if you were to agree, it’s obvious that two years from now, scaling down will not be an option… What should I be aiming for? How do I prepare for that?

    – I’m working on a side project that involves interviewing job experts in montreal (A head-hunter, an entrepreneur, an intrapreneur, a carrer consultant and a work-culture expert) to share the kind of advice you share to students and freelancer to help them accelerate the learning curve and crank their careers on redbull! I’d love to share with you where I’m at with all this, what’s the business model I have in mind and improve it with your thoughts and suggestions.


    – I’m a huge fan, I know your stuff work and I’m ready to take action. I am not going to waste your time and generosity.

    – I’m aware I have lots to learn. I’m only 21 and I believe that what I shared above is of course the result of taking risks and putting efforts in my dreams, but more often than not, also an extreme amount of luck. I have no power over luck, however I’ll keep putting as much efforts as I need to and keep improving.

    – Did I say I love learning? 🙂

    Thanks for all the GREAT content.


  17. Hey Tim, Ben and Reid,

    I’ll spoil the surprise, this comment is a shameless attempt to garner your attention, while presenting my case for mentorship, and adding to the aggregate comment insight on the post. I believe brevity is best.

    The post itself took me down the path of recognizing just how powerful this concept of re-framing risk has been in my career, and although I have experienced it, I never vocalized it as you have in this post. It’s a combination of empirical evaluation, coupled with viewing evolutionary instinct in the light of objective truth. I most like the way you’ve laid out a lens through which you can explain and interpret decisions that the “little voice” tell you to go for it, even when the lizard brain is screaming risky…and that explanation can be applied in conversations with yourself or with others. Thank you for providing ammunition to win the battle of championing appropriate risk, whether the battle is with yourself or with those around you.

    Warning…shameless plug:

    If I was going to mentor someone on this adventure, which your post itself provided a great field guide, I would be looking for qualities like tenacity, agility, intelligence, abundance minded, socially capable and willing to jump in with both feet and get to work…wouldn’t be a bad thing if the protege was also entertaining, enterprising and a proven track record of appetite for appropriate risk. I’m ready, I’m able, let’s do this!

    1. “Thank you for providing ammunition to win the battle of championing appropriate risk, whether the battle is with yourself or with those around you.” Love the way you put this – battle with yourself (which is often the case) or with others….Thanks for the comment!

  18. Hello, My name is Ian Robinson.

    I’m just wrapping up the first week as an intern working with the premier authority in outsourcing here in the Philippines. The above post resonates deeply with me because I believe in taking risks and shunning the voice of apprehension.

    Change in 30-60 days: I want to find massive success in this internship. Within 30-60 days I’d like to grow revenue for the company by more than I’m being paid. At the point in which my value is undeniable, I’d like to propose a new compensation program.

    Thinking of the Risks: The primary risk will be in attempting to fill the shoes of the expert who is already dominating in the industry. I anticipate daunting decisions ahead on how to proceed with growing a brand that already has a large audience who are passionately loyal… to someone else.

    Thanks heaps for the opportunity – I would deeply appreciate the opportunity to benefit from your high-impact session.

    SALUD 🙂

  19. I believe our ability to manage risk is trained into us through how we manage stress in our lives.

    Because of a family’s friends illness I left my home country 3 years ago with my wife and young children to a country where I did not speak the language but I was extremely motivated to help our friend. I gave up my career, my language and even my precious driver’s license.

    It has been a difficult path but I am stronger and wiser and I am willing to share with those who are willing to listen. It is from others how I learned to deal with all the change.

    I now have work, I speak a new language but sadly the friend I came to be with has died.

    Funny thing is that when I share with people the risk I took. They are shocked since I am not young.

    The only risk in life is playing it safe.



  20. I’ll keep this short since I just scrolled down and saw how much you guys have to read. Sweet Jesus.

    Name: Joe Joseph

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

    I am quitting my dead-end job in rural VA and now am currently developing an iPhone app (4HWW style by outsourcing it all :D) to put out in the app store by the end of July. Currently choosing developers and graphic designers.

    I have an empty year where I’m doing nothing but applying and interviewing for medical schools…so now’s my chance to take huge risks and have some


    Would love advice related to entrepreneurship and how best to market my app.

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

    I’ve hedged some of my future career risk by buffering myself with medical school in the future. I can just take a military loan to cover that cost no problem. Although nearly all my resources are going into my iPhone app, I can crash at my parents place or cousins’ places if it all goes to hell. I don’t have much money, only a few thousand, but the upside for apps is the freaking sky, so I’ll take my chances.

  21. My name is Doug and was ‘lucky’ enough to get a job right out of college in 2005. I was making 10k+ more each year I worked there, but the hours, company, environment, and even industry totally sucked. I wasn’t fighting the good fight and it was really affecting my mood and health overall.

    So I quit. I didn’t have a plan, really…just some ideas. I guess that was a pretty big risk, but whatever… I was unhappy and wasting my life, which was worse than anything else i could think of.

    I decided to travel. I knew someone in australia so i figured ‘why not?’ i sorted out a visa and with some clever CC signups, i flew there for free. i went to Vail, CO with some friends for snowboarding and then left on my own for month in NZ and 3 in Aus. It was amazing.

    At the airport, my friend bought me a copy of 4HWW and it’s been a whole knew ballgame ever since. I came back to the US to start my empire with a book full of ‘muse’ ideas i had while travelling….

    And then it all got complicated again. I work at a startup that has a great team, but makes no money and has no business acumen. I am trained as a developer, and i am the only one on staff, but i don’t want to spend all day at a keyboard staring at glowing rectangles.

    I have all these ideas and no idea how to start. Networking isn’t my strong suit, as im sort of shy and awkward. I’ve tried so many ‘lifehacking’ techniques and some of them help but i still feel like i’m wasting half my day and getting less done than i should. I’ve built a few half-products, but it seems like whenever i run into a roadblock, some OTHER idea all of a sudden seems more likely to succeed so i swap focus to that one, until i run into a roadblock. rinse. repeat.

    im torn between leaving the startup and going out on my own and sticking it out. I really just need someone to kick my ass and tell it to me straight. my family is almost TOO supportive (100% not a complaint…i love them all dearly, but they never say anything sucks).

    I’ve read 4HWW, the Lean Startup, E-myth, and a few other books. but reading books != getting things done.

    I think that i could really benefit from someone who’s been there telling which ideas suck, which have potential, and which ONE i should focus on.

    Please help Ben, Reid, and Tim!

    ps thanks for reading all this, even if i don’t get picked.

  22. After college I started a software company to pay the bills. It was actually motivated by Tim Ferriss’ Speed Reading section in the 4HWW. I figured if he could make that much in a single class, what was stopping me from doing the same thing? That brought me into online marketing, and gave me my first taste of truly passive income.

    While the software company is still running and making money, I switched my main focus to online marketing. SEO is what I offer most of my clients, but every now and then I’ll mix in some websites, Adwords, or general online consulting. My clients love me, my business mostly runs itself, and I have contracts for months ahead. I enjoy growing the businesses of my clients, but I’m not sure how much longer I want to keep doing this. I’ll be bringing someone on to run the company, and will be shifting my position to pure owner.

    It’s not that I don’t want to work, I just want something that can impact more people. I’ve always been fascinated with learning, and hate the way the current education system works. While there are some exceptions, teachers are using teaching methods that haven’t changed in over 100 years despite updates in technology and research on the mind. I hate when I talk about speed reading, and people think its a gimmick. Ever since Evelyn Wood (~60 years ago), there’s been courses readily available; yet most people won’t accept it as a reality.

    That’s my new goal. I want to change education forever.

    The risk I’m taking has already begun. Last week I put a significant amount of money into the new software I’m having developed. I’ve had the general concept laid out for the past 2 years, but finally took the time and figured out exactly what needed to be done to not only make the software more effective, but grow the brand and influence the largest number of people. It brings the social factor into learning, which I don’t think has been done before.

    The easiest way to describe the software is Rosetta Stone for anything. It focuses on progressive learning, meaning the material gradually becomes harder which will help with retention. I’ve also mixed in mnemonics (memory techniques), just to ensure that people are actually learning the material. The best part is, you can add in your own information and it will teach you anything. Famous people, presidents, states/capitals, countries/locations, painters/paintings, composers/songs, etc. It’s limitless.

    (I’m not worried about having this information out there. If you want to build it as well, please do. The thought of competitors and the challenge of building a better software sounds motivational. And what it comes down the biggest benefit will be to the end user). PS> My branding kicks butt.

    I’m really excited for the 4 Hour Chef to come out, as I know Tim will be talking about learning and education. I’ve heard him talk about languages, but would really like to see a more comprehensive view of his thoughts on learning as a whole. Hope you didn’t mind the ramble, it felt good putting it all out in the public.

    Thanks. ~Ryan

  23. Nice post guys. Roy here.

    After being dissatisfied at my job for the past year, I decided I could take no more and put my two weeks in without having another job lined up. It was secure, and I was making good money, but I was very unhappy. Some days before work, I just felt like crying before my day even started.

    Knowing I was leaving this job, I immediately booked a trip to Denver, Colorado (1100 miles away) to line up housing and job interviews, as I have wanted to live in Colorado for years. I leave next week. I figure if I’m leaving my current job, I might as well be starting another job where I have always wanted to live. Somehow I am taking action based on faith that I can get a job lined up once I get there.

    Risks? I have a house that I now must sell or rent out. I have a son who is coming with me. His mother is too but we aren’t together, she’ll be staying with her family nearby. I know no one in this area but I believe with my past experience in sales and my work ethic, honesty and drive, I will have employers interested in speaking with me. I have just enough savings to get there, and survive approximately 1 month until my checks start coming in. How am I thinking about the risks involved in this move? Worst-case scenario I move back to where I have family, lose my house, and find work with relatives. It’s a little scary and I kinda feel crazy but I can handle that risk for the chance to make better money in Denver and live in my favorite state…

  24. Hi Ben and Reid ~

    This is Jill Rowe. My career to date has been full of taking risks. In fact, I don’t think I know how to navigate without that component. My latest risk is at 51 to be ‘starting over’ in a new arena ~ branding. The career risk I’m taking is to endeavor to play with the big girls (and boys) in a field that I have a lifetime of peripheral experience in. I’ve offered my services for free to build my business, make contacts and gain useful knowledge that I will use as case studies. The risk (although I don’t see it as a risk, I see it as a necessary step) I want to take in the next 30-60 days is to suggest a project to a high profile client in my field that will be useful to them and give me an opportunity to showcase my talents.

    To be humble (open to learning) and play ‘as if’ at the same time.

    I’ve been talking about the fight or flight idea for several years and I too feel our vestigial fear-based brains are holding us back. I want to use my knowledge in this area as an integral part of the way I will help others overcome their obstacles and utilize their unique talents as a brand to catapult them to the forefront of their respective fields. I would be strasopherically stoked to have the opportunity to learn from the two of you.

    Thank you!

    Jill Rowe

  25. This article is fantastic and has defined all that I’ve been feeling for the past couple months. As of yesterday, I have put in my notice to pursue what I feared was a selfish risk to take, but in my gut it felt right. This article has helped me realize that I’m heading in the right direction. Yet, some mentorship would definitely be helpful as I’m just embarking and perhaps still making some questionable risks. Let me explain.

    I am still pretty green in my career path, but I stumbled upon my position as a bid proposal writer at a small corporation about a year ago. It is full-time telecommuting and offers a higher salary than I’ve made in my life. I was a teacher and then a curriculum developer, and the position pulls my experiences in both positions and applies it to the business world. Although I’ve learned a lot from this position, it offers limited growth and I’ve pretty much learned all that I can from it.

    More importantly, over the past year, I’ve also discovered my passion for sustainability and water conservation. I’ve volunteered, participated in training, and attended conferences in my passion. I’ve read lots of books and made plans. But last month, I realized I needed to take the next step and transition into work that aligns with and takes me on the path towards my passion. Recently, I found a part-time position working with a non-profit that goes into schools and works with teachers to present standard-aligned, water conservation curriculum. I’d be giving up benefits and an excellent salary to work for about $10 an hour and 19 hours per week. After running the budget, I realized that my husband and I could survive with some left over as long as I had another part-time job to supplement. A former colleague of mine recommended Trader Joe’s or Whole Food’s because I’m interested in sustainable food production. I successfully interviewed with Trader Joe’s and got a position there. Meanwhile, yesterday I was offered the position with the water education company.

    By that point, I had struggled with the decision to give up the salary and full-time job for part-time work that may or may not be “stable” and definitely may pay less. I had a couple weeks of restless sleep and anxiety-ridden days (negativity bias at work). It didn’t help that my husband’s work is going through the changes of a new acquisition and his position was (still is) potentially at risk and at the very least being redefined under new management.

    But you know what? Nothing is as stable nor unstable as it appears. I decided that I wasn’t going to be ruled by fear and what-ifs. I can’t keep working at a place I don’t feel passion for, that’s going nowhere, and that isn’t helping me grow just because MAYBE my husband might lose his job. Now, it’s still a controlled risk–I’m still going to make enough money to live and save a little. But the opportunity to work with the non-profit of my dreams trumps the cash the corporation is willing to pay me.

    Still, I have fears. Enough that I’ve offered to work part-time/contract with my current work just to have a back-up plan as neither of my new part-time opportunities can guarantee 20 hours every week. And though I’m really leaving to work in water education, I fear that it’s stupid to party quit an OK salaried/professional job to work at Trader Joe’s. I’m afraid that part of my temptation to work at Trader Joe’s is that I just want to get out of this current job (or at least be able to get out completely) rather than it being a gig that’s going to help me get on the right path.

    Still, I’m very excited about the potential of the next 30-60 days and all the changes that may come. In addition to a complete change in my work, I’m also going to invest in a couple landscape/gardening certifications and a course in landscape architecture at the local university. Depending on how this course goes, I am considering completing a Master’s in Landscape Architecture next year that will give me the skills to apply my interest in sustainability and water conservation to designing public outdoor spaces. It would be ten grand a year for a minimum of three year’s investment. If I take the risk of investing in this degree and gaining the licensure, I don’t plan on relying on it alone. Rather, I will gain experience in the field while learning.

    What risks are worth taking? Well, I don’t know how these risks will pay off and have doubts beneath my enthusiasim. But, as Anais Nin puts it, “And then the day came when the risk to remain tight in a bud was greater than the risk it took to bloom.” Well, today is the day. In fact, today is always the day, but it takes awhile to realize it.

  26. I am working at the civil service in germany and have no risk at all. Thats very boring an I am studying beside this to help me staying alive… I have the opportunity to apply for CEO in our little company. I know everyone will laugh at me because I am only a little nobody right now. The problem is only in my head: I dont want to be made fun of- although I don´t know if it will be so… What do you think?

    All the best


  27. Taking Risk is more of a habit to me cant live any other way, , Once you have an open mind with an intention of doing good. And to make others and yourself happy by doing something unexpected every single time. All the doors to success open to you by default cuz everyone wants you to succeed and grow..

    My principle in life is.

    Whatever is going to happen “IS” Going to happen


    Whatever happens , always happens for the Good.

    I repeat these words to myself every single time I achieve or fail. Turns all thoughts into positive ones making your capabilities limitless..

  28. I would suggest that there’s a missing component here, and that is: You not only have to have the willingness, but also the capability, to take career risks.

    Student loans tie you down. A mortgage ties you down. A wife and kids tie you down. These commitments make it much more difficult (although not impossible) take big risks. Therefore, take the most risk when you have the least to lose – aka when you are young. Or, if you already have a lot to lose, limit your risk by eliminating debt, starting off by moonlighting, etc.

  29. I’ve spent the past 6 months living a very uncertain life. Leaving the cushion job with benefits on the east coast to come out west to be with the girl and really “get my career going” has left me hanging out in the So Cal heat to dry. On a daily basis I find myself questioning everything as the extremely uncertain political and economic state of the nation suffocates me.

    I’m constantly looking for ways to expand my entrepreneurial thinking and brand myself, reading books such as “The Four Hour Work Week”, “The Education of Millionaires” and currently “A New Brand World”. I soak in the valuable tips of reinventing myself, axing the traditional methods of finding a steady 9-5 job by sending my resume to hundreds of employers that will never understand the value I’d bring to their company from a piece of paper. Unfortunately coming up with numerous “a ha!” moments and ideas has gotten me nowhere because of the risk and financial burden it would bring upon me. I find myself all over the place with ideas that I don’t know which to focus my time and energy on. And at the end of the day I must still spend my time applying to those temp positions in order to pay the bills.

    The change I’ve been wanting to make in my career is something that I thought would have occurred by now. Living in So Cal as a creative video producer has made me realize I’m a drop in an ocean of talent. I won’t accept that current lifestyle of waiting for the next freelance job to come around, to work on that next film or commercial like the many others. But I’m afraid my wide range of talents and experiences are keeping me from focusing on that change I want to make. I’m all over the place and terrified of making a big mistake with a risky career move, because as much as I read about how healthy it is to have failures when starting a business, I can’t accept failure right now. I’m certain about everything in my life right now, my soon-to-be fiancee, my amazing friends and family back east, my talents and ability to lead and run a company, but it’s that uncertainty of starting it, the costs from the get-go, and getting the clients that has been holding me back.

    I’ve been putting a lot of thought into opening my own multi media studio. I’m struggling to find that niche but I have a few ideas to bring to the table. The risk involved could be minimal, I just need a nice small studio to work in, a white backdrop, some lighting and a camera. My goal is to expand it into a larger space, but that’s down the road. For now I’m confident this is all I need to get my idea going, I just need to learn how to deal with the uncertainty.

    It’s one thing to read all these amazing/insightful books and posts about taking the risk to avoid a long term unhappy and cushioned lifestyle. It’s another thing to act on it. I hate myself more and more every day for not creating something for myself and my future wife by now. I envy anyone who knows what they were put on this planet to do, because it’s f’in frustrating fearing going down a specific career path because I’m afraid it’s not what I was meant to do. I could use the push and investment you guys are offering, and I appreciate the opportunity.

    Thanks for listening!


  30. Good morning, gentlemen; I am Cheryl Obermiller, former model and agency owner, mother of 8, grandmother of 13, host mom to 9 foreign exchange students, married for 27 years, certified scuba diver, overcame my fear of heights by climing Mayan pyramids in Belize, run 3 miles every morning prior to doing a weight workout, and love to cook! (I live in an area of the mid-west where the two basic religions are Baptist and BBQ, so we cook out a lot.) In 1993 I founded my own heavy construction company, and by 2000 had turned it into a multi-million dollar business. (My kids used to tell their friends, ‘Never annoy a woman with her own backhoe, because she can kill you and bury the evidence. Our mom has two…’)

    In 2010 I discovered that my long-time company accountant had, over the ast eight years embezzled around a million dollars and almost bankrupted me. (Check the web under Obermiller Construction embezzlment for info. She was convicted of stealing $473,000 in 4 years, but due to statutatory limits the FBI did not go back the full 8 years.) She reported to prison for a three year sentence in November 2011. The financial devastation was almost secondary to the emotional trauma – I cannot even describe the full impact of such a crime. In fact, one of my most passionate ‘bucket list’ goals is to spend the rest of my life avoiding anything that could possibly result in needing the personal services of an FBI special agent – once was enough!

    I am writing a book/program for to teach small business owners how to protect themselves from financial fraud, which is called “My Accountant’s Drawers ~ the Small Business Owner’s Guide to Outwitting Embezzlers, Theives and Scallywags.” A small business (less than 100 employees) is literally one hundred times more likely to be a victim of financial fraud than a large company. Additionally, the owners are often personally bankrupted by the failure of their business. Most entrepreneurs do not have formal business training (and even those with business education probably have little to no idea of how to prevent or detect embezzlement.) As their businesses become successful they hire accounting help, but have no idea of how to effectively oversee their work. This opens the door for fraudsters to come in and rip the guts out of the company, while the owner has no idea what is actually happening – frequntly until it is too late to save the business.

    Over the past couple of years I have read thousands of fraud cases and been completely blown away by the very basic and simple-to-catch tactics used by over 90% of embezzlers. Most business owners don’t understand the risk of fraud in their own organizations; they are creative people who love promoting and expanding their businesses but hate paperwork. This makes them – US – easy targets for financial disaster.

    My goal is to complete my book this summer (our youngest daughter just graduated and is off to MU in August, so I will be a free woman for the first time since 1977) and then travel around promoting it and speaking on financial fraud. This will require that I step away from my mostly-recovered, multimillion-dollar construction company and let three of our grown sons run it. Gulp – talk about the ultimate fear factor!!! Think of giving your kids the car keys, and then multiply that feeling about a million times!

    On a serious note, I have developed a complete, easy to use system that will prevent most common fraud, and have written it in an entertaning, step-by-step way that busy bosses will actually read and use! You know how meaningful it is for you to teach people how to build their dream lives and businesses – now you have the opportunity to help them protect those dreams from being stolen or destroyed by others. I would truly value your input and advise as I start this new and exciting part of my career and life! I am so excited to share what I have learned, and also to show people that injustice, financial hardship, etc., can be the foundations of a new life instead of the ashes of an old one!

    Additionally, I have hired a software developer to design a covert program owners can use to monitor accounting activity, but I don’t want to write about it on an open forum as I have not filed my patent yet. I can discuss more details about this project in private.

    I look forward to speaking with you,

    Cheryl Obermiller, President

    Obermiller Construction Services, Inc.

  31. I’m Aaron Carver, 19, a college student now double majoring in Chemical Engineering and Computer Science.

    I already mentioned my first change–adding a degree in Computer Science. After I finish my first programming class this summer, I will add a CS major. This makes me a bit nervous because it is extra work and I’d have to take a lot of hours to get the degree without adding years before graduation. But the way i see it, I’ll not only leave school one step into the tech industry, I’ll be learning how to be a dynamo learner by taking extra hours and two majors.

    Next, in 60 days I will be leaving for Washington, D.C. for a congressional internship position that will last 4 months. The opportunity sounded so incredible that I could not turn it down, despite it being “outside my major”. If anything, that is the reason it could be so valuable for me. I applied for the position a few months ago, and now I’m very glad I did. It’s a new experience of working in a different environment, a different city, with a group of highly motivated people. Within my study or not, this will be a great opportunity.

    Third… This is a mini-retirement in the making. I have a friend who is a native of Thailand. He is planning on going back next summer for 3 months to stay with his mother there, and he made it known that he would like it for a friend to come back with him. This is an opportunity to spend 3 months in Thailand with a native who I know personally. There couldn’t be a sweeter deal. So in the next 30-60 days, I want to start making small plans and some commitments to going (i.e. get a passport and look into the requirements for the trip, talk frequently with my buddy to start making the idea real.) I’ve never globe-trotted on this scale before, so I have some butterflies about the trip, but I want to start taking action so that I’ll go through with it.

    Also, I will be applying to the Semester at Sea program. It’s a study-abroad program that circumnavigates the earth over 100 days teaching students global education while landing in a dozen countries along the way. I’ll be applying for the Presidential Scholarship, a full-scholarship offered to only a few students a year. Again, it gives me a few butterflies, but if I take action, I won’t miss the opportunity. If selected, my voyage will start in January 2013.

    During the next 30-60 days I’ll also be looking for new internship and travel opportunities for the future. Right now I’m working on what will happen over the next 12 months (internship in Congress, study abroad, trip to Thailand). I want to start contacting people and lining up next year’s adventures, maybe an internship near Silicon Valley (!!!) or a NOLS internship in Patagonia (or both)!

    Every time I find a new opportunity to travel or intern somewhere cool, I feel that primal instinct of worrying about the risks…But the more opportunities I step into, the more I outgrow that perspective.

    I’d love to talk to you guys, I really think you could inspire me and help me make some opportunities happen.



  32. The change that I would like to make in the next 30 days; nay, the change that I will make in the next 30 days, is that I will open up an office for my newly founded business in Costa Rica, Soluciones y Redes del Oeste, S.R.L. Why this may not seem challenging to most of you out there, and why it is a great challenge to me, is because I barely know anything about IT and Computer Networking and that is exactly what the business is! I always wanted to own this type of business and I have a passion to learn the business, however, I had initially planned on partnering with another individual that had the knowledge and I would just take care of sales, as well as the day to day operations of the business. That individual turned out to be a flake as well as a dishonest person; neither attribute being ones that I want associated with my business.

    I have all the licenses necessary, I have formed the corporation and begun to get the suppliers that I need, and I am hiring people to perform small tasks for me in order to ascertain if they would be reliable subcontractors for Soluciones y Redes del Oeste, S.R.L. Additionally, I have rented an office and paid three months worth of rent, which includes a communal secretary and utilities are paid. I am also building up inventory. My biggest challenge is to continue to fake it until I make it; yet, be credible to potential customers by learning the lingo and being able to identify such customers’ needs.

    Another challenge is that I am in Costa Rica and the attitude down here is “Tico Time” (I actually have this tattooed on my wrist, beneath where I wear my watch. Tico Time just basically means, “I’ll get there when I get there.” It reminds me of a contractor that I used to perform building inspections for who had started his business in Hawaii…”Not Just When the Surf is Low Construction”! So, it has been hard to get where I am at, but I’ve made it this far and refuse to stop…too much momentum to turn back.

    What I want all of my potential customers to know is that they are in good hands, their work will be carried out on time and to the specifications and or requirements for their needs. A smaller challenge is that, I keep getting a lot of customers for cctv security camera installations and I need to take advantage of this business, but not allow for this to detract from the business’s focus of IT & Computer Networking.

    In terms of how I feel about how I am thinking about the risk involved, I am fearful that I will take on too much work and not be able to satisfy my customers; I am fearful that the people that I hire will flake on my customers; I am fearful that the people that I hire to do the work will steal my customers; and I fear that I am spending too much time working on the image of the company without taking enough time to learn more about networking…the core of my business.

    In closing, I want to thank you, Tim, for always providing extraordinary content in your blogs.


    Glen Adkins Jr., RCI

    Soluciones y Redes del Oeste, S.R.L.

  33. very interesting stuff here.

    I’m a software engineer at a large corporation looking to downsize – significantly. Mostly I want to be in a shop where I can make a significant difference to the company as a whole, so I’ve been looking at smallish (~20 people) startups.

    I’ve considered various factors – moving cross country, my personal and professional relationship, and my financial situation. The last one is the killer – with student loans equally more than a month’s rent for the vast majority of the country, I’m very limited (at least it seems so to me) in my opportunities.

    However, the big motivation and biggest opportunity for me is to be happy – I’ve noticed that I excel and thoroughly enjoy situations where I’m given the personal resources – time and, mostly importantly, freedom – to get the work done how, when and where i want. A smaller company is most capable of providing me these types of opportunities.

  34. I took a big risk 6 years ago and abandoned a promising public service career to move to South Korea. Now I’m married and we have our first child on the way and I desperately want to move back. In terms of my career, I have a short-term problem, and a long-term problem.

    First, the long-term: I have no complaints about my job. While last year I was making the most money in my life at the worst job of my life, I quit that job and this year I’m making less than half of that teaching Political Science at a University, a job really beyond my qualifications, but I believe I’m doing a great job so far and my wife and I are the happiest we’ve been. The way I figure it, that’s probably a way better environment for bringing a baby into the world than we had last year even though the “responsible” thing to do would have been to keep making the big bucks and try to put some away for the family.

    Here’s my conundrum: teaching at the Uni is a great opportunity especially considering I’m doing it with only a Master’s, not a phd. But I have a gov’t-imposed limit in this job of two years before the University must make a a regular, non-contract hire (which it won’t, as I don’t have a phd).

    I need a game plan to make the most out of this current job as I possibly can. This means publishing in academic journals, something I am woefully rusty on. This also means identifying what’s next and setting up a game plan. I’m thinking a phd program, but that also seems like it would take us farther from our goal of eventually moving back to the US, as I couldn’t afford to do a phd program in the US, and doing one in Korea probably wouldn’t be respected in the states.

    Short term problem: Baby on the way and not much income to cover the expenses. We are barely breaking even now, and that’s with me teaching extra overtime classes that I don’t know if I will have next semester. I have some ideas on how to supplement my income (some self-publishing projects and a possible small business), but I know that pursuing them takes away from the long-term goals and it’s been very challenging balancing the two focuses (in fact, I can say that so far, I’m failing).

    All in all, in terms of the risk, I am on a clock. In Korea, it is unlikely that I’ll find another job like the one I have now. It is guaranteed that I WON’T find one like this in the states unless I get a phd (and even then, the academic road isn’t easy). I feel like if I don’t play my cards smartly, I won’t ever have a better springboard than I do right now. But springboard into what? When the clock runs out, It will be my best chance to make a leap in my career that I have ever had, perhaps in my whole life. I need to hit that springboard hard and straight to get the most bounce as possible.

  35. Perhaps the most interesting idea to explore in Mr. Hoffman’s post is that of volatility and the role it plays in both business and life. It is the frequency and magnitude of activity that leads to volatility in most data sets. By activity, in life, I mean accomplishment of worthwhile and meaningful goals. It is important to view our activity as a time variable that is not constant and can be sped up and slowed down or compressed and decompressed. Activity can also have negative or positive outcomes. This is why focusing on building non-correlated passive cash streams is a great idea. Consistent profitability coupled with the shot at superior gains is the formula for success in business and life. When the correlation between your time and your money start to decouple it affords you the opportunity to swing for the fences.

    Why is a book about applying the principles of entrepreneurship to life important? It is because all of human endeavor is related, success in one area is very helpful in success in another. This is why I would like to speak with Mr. Hoffman about my new project. A book with the working title of “How to lose at cards consistently and in the long run”. Thank you for your consideration.



  36. Hi, I’m John. I’m 27 years old, and it looks like I’m going to be a father soon. To be quite honest, I’ve never really made money a priority in my life. I’ve always made learning and self growth my priority, focusing on how to continually need less. I want to change that now.

    Let me tell you a bit about myself. My wife, Khylynowey, and I live a very different life form most folks. We met at a nine month wilderness survival intensive in Washington state, and later got married, barefoot, in a dirt floored hut in Washington’s beautiful rainforest. We’re not hippies, I swear. (Check out the pictures at, under Our Wedding)

    When I develop a passion for something, I tend to jump right in. For example: last year, after moving to Canada with my wife, I decided to build us a cabin, with no previous building experience (photos on facebook, under Home:Made) I’ll admit that it might not be for most people, but it’s just right for us. We cherish a simple life that allows room without distraction for us to focus on self-development (which in my case means practicing the guitar, kung-fu, and naturalist studies) and enjoying our time with each other.

    I truly believe that this world is rich with opportunities, and I want to make as many options available to my child as I can. I’ve read and been inspired by Tim’s book, and now I’m ready to jump into the world of business, but I could use some guidance. Sure, I’ve got a few app ideas, and I’m looking into developing them, but I need to do some more research first.

    I don’t want to have to work all the time to support my wife and child; I want to be with them. I’ll only get one chance with this child, I can’t afford to blow it. I may be new to business, but I am a very fast learner. Give me a shot; you won’t regret it.

  37. My risk is starting my own company. I started a company before but it wasn’t something I really enjoyed but it was successful and now my family is running with it. I took a job at a starting level to learn more about content production and internet marketing. For my next company, I want the focus of my new company to be on turn-key video marketing from scripting and production to integration of the videos into a youtube/video SEM and trueview campaign.

    I’m a little uncertain as to how to get the initial investment money. I can take a loan to start it off but I’m also saving for my wedding and I’m not sure if I should make the investment given the fact that my technical video production experienced is a little limited.

    How am I perceiving the risk? I think the initial investment is not big enough to scare me even if things don’t work out at first. Another concern is that the video quality won’t be that great and that I’d ruin my chances of having word of mouth.

    As I’m writing all this I realized that for me this risks are minimal compared to working for someone else on a 9-to-5.

    Even if I don’t win this contest, I want to thank you for making me think aobut this fear in a more concrete way.

  38. Hey guys. I am 24 years old and the founder of a philanthropic clothing line. We are a Portland, OR based company that is working to use apparel to put an end to the water crisis. Every item purchased provides one person with access to clean drinking water for 25 years. We do this through a partnership with a non-profit that builds wells and water purifiers in Africa, India and South America.

    After market testing and customer feedback, we have realized that we need to make some changes in our current line if we are going to be effective moving forward. Since we are bootstrapping, this transition is not going to be easy to do with such limited resources. My degree is in finance and I have recently been searching for entry level positions and weighing my options. I have also researched and talked to wholesalers about new items in order to transition the line. I have done the research to move forward in either direction but I’m having a difficult time deciding what is the right choice. Starting this project was scary enough. Now I feel like we have hit the “dip” as Seth Godin would say. It is clear that this business is my passion and what I want to be pursuing; however, sometimes you reach that point where you have to make the difficult decisions in life and consider “what is the responsible choice?”

    I am glad to say that your post has come at the perfect time. After considering the points that you presented, the decision has become simple. By pursuing an entry level finance position, I am allowing the traditional mindset to lead me in direction that I want to avoid and as you have proven, is more risky. I have learned more by starting this business than I learned all throughout my undergraduate. By pushing forward and releasing this new line, I will continue to develop skills, provide value and create more opportunities in the future. If this pivot in our strategy pays off, we could accomplish our goal of providing thousands (or millions) of people with access to clean water. To take an entry level finance job and place myself on the same playing field as thousands of other recent college graduates would be the real risk.

    I am happy to say that I am putting my resume away and planning to release the new items in the next two months. I would really appreciate the opportunity to talk with you both and learn from your tremendous knowledge. The value it would add to our startup would be tremendous and could ultimately impact numerous lives around the world. Thank you for the great post.

    – Kyle Morrow (Chief Thirst Quencher)

  39. Thanks Ben and Reid (and Tim for having them guest post), you articulated much of my thought process over the past two years which are now culminating in the next two months of changes. I can’t reveal too much of my life story publicly as my future employers could find this but hopefully this will resonate enough.

    I am in my mid-30s and two years ago I left my full time job and six figure salary as an IT manager at Fortune Global 500 company in North America. I went to grad school in France in order to change my geography, function, and industry. I am now closing in on a job offer as a product manager in Japan in the ecommerce industry. I had offers from Europe and North America with far higher pay, but this offered me everything I was looking for, except the salary. But I knew that this is the offer I needed to take. I held out six months after graduating to find the perfect opportunity, and I think I found it.

    Kahneman and Tversky were spot on – losses do hurt more than gains feel good. I learned to fight my loss aversion through some unconventional methods – I lived on the streets for a week with no money, just new friends and a lot of humility. I learned that having nothing doesn’t mean you starve, at least not in a developed economy. I learned that I can survive as long as I had the knowledge in my head and the willingness to accept the kindness of strangers when necessary.

    So from this, I knew I could take risks like lower pay and and still be ok in life. But I also know that there are those that depend on me, namely my wife and future kids, that I cannot let down. So I must take calculated risks, with as high a reward as possible with limited downside. By taking a product management role, I am tapping into the same insight that Reid had – it is the heart of a product company. The company is looking to change a whole industry where the risks are highly publicized, as well as take on an American internet giant. In the process, I am looking to find opportunity in the industry shakeup to come to start my own startup, where I can take the lead in shaping the product.

    The other change I am making within the next two months is to develop side income streams – “muses” or “passive income streams.” This is in order to teach myself how to build a business based on an asset, not just a form of self-employment by being a consultant or contractor (which I am already familiar with). This may involve creating an ebook or building an app, or some other endeavor – I am not sure yet as I’m still assessing the opportunities for viability, potential, and my own passion. This is also important learning as I ready myself to build my future startup, as I need to learn skills such as identifying markets in need of a product, and learning how to build awareness in that market of my product. My core philosophy in career and life is to bring value to other people’s lives, so I really need to learn how to understand what people need in their lives that can help them to attain happiness and accomplishment.

    The risk to developing additional income streams is really minimal – I may risk that I am not giving 110% of my time to my new job, but I will consider building muses that will actually improve my understanding of the industry, and in the end add value to my new employer. I am actually de-risking my own future by building a cushion of income-generating assets against the decay of any one economy, industry, or company. If I choose wisely, I will improve my geographic mobility and the ability and choice to work on projects that add value to my own life and to that of others, regardless of monetary compensation. So the risk overall is low (time), and the potential gains astronomical (happiness and fulfillment for myself and others).

    Hopefully this resonates with the other readers in some way – would be great to meet a kindred spirit or two.


    P.S. Ben and Reid, thank you for the unexpected gift – this is the first time I wrote out exactly why I took these recent decisions to act, and it helped me really clarify my thought process and the potential end game plays that I can make in the future.

    1. Awesome – it’s so true that writing out your thoughts on a topic like this can help clarify what you’re thinking.

  40. I quit my job in January because I discovered a problem I desperately needed to solve. My BMW was 6 months and 10K miles overdue for an oil change because I didn’t have time to take it in. I was willing to pay someone to go do it for me and realized there could be an awesome car concierge service built here. It’s like an Uber for car maintenance.

    As a first time entrepreneur I didn’t know the hurdles that I’d have to overcome. I went to oil changers, car washes, service stations, etc. to talk to customers about their biggest pain points of car ownership. Getting any service for their car was a huge overhead. It turns out that I discovered a juicy customer segment of people willing to pay to have this problem solved.

    I partnered with a longtime friend to join me on this mission. We launched the service privately and our early customers loved it. As we worked out all the operational issues, we realized that it just wasn’t a good business. We made the hard decision to shut the service down. Operational costs were high (drivers/insurance) and profit margins were low.

    Now I’m giving myself some room to explore. My mission has always been to create a huge positive impact on people’s lives. There are so many things to build leveraging technology and it’s hard to nail down one. I want to dial in on a huge problem that people can benefit from if it were solved. I know it’s going to be a long and hard process to be a successful entrepreneur.

    This has been a really difficult time for me. I haven’t had income for a long time and am burning cash. My friends and family are concerned about why I’m doing this. They’re conditioned to think that you must have a job. My biggest risk here is my financial situation. I am determined to create a successful business even without income for a long time. Hopefully, I won’t go too far into credit card debt!

  41. This post is SUPER inline with my own thoughts in the two years, and in fact this internal struggle lead me to consider the subject of risk in something of a novel way. First, my profound thought for the contest, then my story. 😛


    Risk is simply the potential that you will lose – high risk == high potential that you will lose. Easy. But to consider risk, we must first define what a “loss” is in the case of our lives. Let’s do that first.

    If you live in America and are fortunate enough to have time to read this blog and consider its implications, you’re probably not going to go hungry. Your basic needs are probably met – and in reality, you are probably thoughtful and resourceful enough that you will be safe from hunger and predators for the rest of your life.

    In other words: you’ve climbed Maslow’s hierarchy. We all have in the First World. But per the post, it’s hard to realize this – that the primary drives for many of us no longer need to be food, or resources (we will have enough of those to easily survive), but in fact it is happiness and self-fulfillment.

    I’ll also go one step further and say that happiness is binary; you’re either happy or not. “Kind of happy” == “unhappy”.

    Now the definition of a loss starts to crystalize. Failure to achieve or sustain happiness is a loss. Being happy is a win.

    And so my profound thought is: when evaluating risk, consider the value of your options exclusively in terms of your happiness (or the happiness of your loved ones). The beauty of this method is that you don’t even initially need to know what makes you happy – you just need to know whether you are happy, now, and/or will be in the long-term.

    In other words, you don’t need to know the destination – you just need a compass. If you’re happy now, and will be long-term, stay put and double-down on whatever it is you’re doing. You’ve already won my friend. But if you’re not, experiment; try stuff until you are.

    __Tl;DR / SUMMARY__

    Don’t evaluate risk in terms of success. Evaluate risk in terms of happiness.

    Understand that if you’re not happy with your current situation, THE RISK OF FAILURE IS 100% BY STAYING PUT. (And the chance of success is 0%.)

    Example: imagine you quit right now and pursued your dreams of starting a rock band, or feeding 100 hungry kids in your hometown (whatever the thing is that you most believe will make you happy).

    Let’s say you have a modest 2% chance of succeeding at it and doing it long-term if you pursued it for real, full-time.

    Now consider your options: (1) 0% chance to achieve long-term happiness by staying put vs. 2% chance of achieving long-term happiness if you go for it.

    Easy decision. Chase it. Chase it tomorrow! You will learn. You will grow. You will not regret it on your death bed.

    __MY STORY__

    I left high school with a passive interest in tech, and went to college for a semester in a hardware/software engineering program. Feeling lost and uncommitted, I left, and at 18 signed on at a call center who serviced a Fortune 500 company (Symantec/Norton). I made $11 and got paid on Fridays. I bought my dream car for $9,500 and a handful of CDs every weekend and had a L-O-T of body piercings. It was 2001, I was in love with a girl, lived with my best friend in my hometown of Eugene, OR, and it was a perfect, amazing, simple time.

    Then I got hungry. For power and money and promotions and praise and all the other shit America is best at. So I got scrappy and made friends and had adventures, and I fought for success. I changed myself. I talked more about things that mattered less. I stopped calling bullshit on people who had mow power than me. I played the game.

    But I made it, baby! After 8 years of effort I’d scratched and torn and climbed my way from a lowly phone jockey with no education to a senior position in the product team managing some ragtag vagabonds (like me!) and making mid-six figs. American dream, right? Now it’s 2009 and I’m 26 and I own a house in Portland, OR. But I’m unhappy.

    I spent 2 years trying to figure out why. I decided it was work. Well, that it was me; who I’d become. Not a bad guy by any means – but not someone living a life true to themselves, either. I knew I needed to get out, and I started finding blogs and books that helped fill my head with ideas – like Tim’s!

    I started moonlighting with a couple friends trying to start my own thing. I tried to have it all; take no risk – just keep working at my big Fortune 500 and hope that something comes together on the side. But it didn’t work.

    So I was faced with a tough choice choice: keep working for the man? Or take a risk and leave? This is how I came to consider the idea of risk, what would be a “loss” to me, and came to the conclusions presented above.

    Given the discussion to this point, it’s easy to guess what I did:

    – 6 months ago, I experimented with a totally new day at, but I had the largely same dissatisfactions (sometimes in new and exciting flavors).

    – 1 month ago, I quit my day job completely, and started teaching myself Rails and other web languages. I cut my living expenses down to the bone. I give myself a 2% chance to succeed – which are the best odds I’ve had in YEARS. 🙂

    – Yesterday, I launched a test site for a silly little mobile app ideas that might make a few hundred bucks if I hustle. 4HWW-style, I’ll run some adwords tests next week and see if anyone cares. Then pivot.

    – In the next 30-60 days, if there is interest in my first idea, I’ll teach myself objective-c/iOS development and build it. If not, back to the drawing board for idea #2. UN-4HWW-style, I’m doing it all myself…but that’s just my way. 🙂


  42. Hey There!

    My name is Jennifer Woodward – I’m married with a 20 month old son and I LOVE change. I’m a community college dropout who has hustled her way to top positions in several companies.

    I’m constantly on the look out to make the next big __________ happen!

    In the next few months I’m looking to replace the income from my day job (which I took to avoid the risk of continuing to work on a grant funded project that was ending = mistake). The challenge = I’m launching my own business, freelance writing, and launching a speaking career – none of those activities are paying the bills, yet.

    The risks I’m looking at are income driven –My day job isn’t meeting the dollar amount we need each month but it is stable and pretty guaranteed. My own work is showing great potential and receiving good reviews but not yet paying.

    My general thoughts: Do I find higher paying day job? If I do, will I have time to continue on my own work or will I have to put it on hold, again? Do I continue to stick it out at this current job and dive full into my own work? How long will it take to see a return and can we survive the income shortage for that length of time?

    My thoughts on the risk in this move: I’m risking more by doing nothing.

    Have a most fantastic day!


  43. I just finished reading the book ‘The Start-Up of You’, viewed the 10 videos on the website, and just now finished reading the blog above. All very inspiring !

    My background is in Accounting and Finance, working as a Controller for small businesses. Right now, I am trying to pivot to my own Plan B, and frankly, am positioning myself for that breakout opportunity. Let me explain what I mean.

    Cloud computing has come a long way from when it first came around a few years ago. I think people are beginning to see that security is not really all that much of an issue, and that it is actually more secure. Working in the cloud also allows massive integration of all aspects of the business cycle. Lead generation, sales and marketing, CRM, order placement, payment, E-commerce, website management, inventory, ERP and financials can all be seamlessly brought together. One company that is doing this very effectively is NetSuite, and I am sure there are many others trying as well. So my pivot is to train with NetSuite with their software and products, so I can provide my consulting services to the many start-ups, small and mid-sized businesses. I feel my career could completely take off if I can do this effectively. And yes, there is a lot of primal fear holding me back, even while I am seeing a lot of opportunity.

    Having Ben and Reid mentor me would be a Godsend. And as I read all the other comments above, I do wish everyone good luck as well.

  44. I definitely could have used this a few months ago. I’ve taken many risks over the past few years, but having weighed the pros and cons and took the stance “what’s the worst that could happen?” it has led me to a much happier place.

    – Two years ago I left the company I had been with for 8 years for a new opportunity and with the intent of relocating. It was just time to move on.

    – First day of the new job they told me I would not be relocating. The manager I was supposed to work for had also quit while I was in the hiring process and I was now reporting to someone who didn’t have a good reputation.

    – I decided to stay and try to make the most out of it. When things weren’t going the way I wanted them to go, I applied internally for another position which caught the attention of my bosses boss.

    – He tried to convince me to stay, offered me the responsibility I had been asking for for 9 months, told me I would need to work more hours, but they couldn’t guarantee me a raise.

    – Just as I was about to start looking to go somewhere else a friend called me and said a team in her office was looking for a good engineer with leadership capabilites and they were willing to provide training.

    – I jumped at the opportunity, moved into a totally new industry, started over, and am loving every minute of it!

    Bottom line- get out of your comfort zone, challenge yourself, and find something that makes you happy and that you’re proud to be a part of. For me, I wanted what I spend 1/3 of my time doing to actually matter and be important. Good luck to those on the search for something new!

  45. Great article. It has slowly become apparent to me that taking career/lifestyle risks is actually the *least* risky thing we can do with ourselves long-term. I need to constantly be reminded of this. Our endless list of cognitive biases make rational decision making such a chore. I guess it’s analogous to hedge funds in many ways. They are limited to accredited investors; advertised as being “too risky” for the layman — yet they nearly unanimously outperform the financial instruments open to the public.

  46. I heard it many times going through college…big risks = big rewards. I also heard the advice to take a job with less pay and more training than the job with more pay. Obviously, being an entrepreneurship major I heard that you’ll fail 10 times before being successful.

    BUT…entrepreneurs are said to be risky. It’s stated in the article that business is a risky job, entrepreneurship and starting your own company is a risk. However, I think that entrepreneurs are less risky than people think. We don’t jump off a cliff hoping to find a parachute. We look for the parachute hanging on the cliff halfway down, get out a calculator and measure the exact physics needed jump just perfect, catch the wind just right, be facing the right direction and have enough strength to grab the parachute on the way down…THEN we take the leap. We take calculated risks, which if we’ve calculated correctly are little risk at all, and are in fact more opportunity and reward. I don’t think you have to actually fail 10 times before hitting it big. I think you’ll have 10 failures of an idea but you should realize the potential failure long before the “riskiness” of that idea lets you actually fail.

    It’s not avoiding risk as suggested by our nature. It’s calculating big risks tied to big rewards, and then finding a way to mitigate that risk as much as possible without compromising that reward.

  47. Since I graduated college in 2009, I have worked at a small (9 people) wealth management company that provides wealth management services for individuals and defined contribution plans. My job has ranged anywhere from answering the phones, to performing security analysis, to creating and producing performance reports for 401(k) investment committees. In the process, I have acquired my securities licenses and just finished sitting for the level II CFA (chartered financial analyst) exam.

    I have been “priced out” so to speak in my current role at this firm. Given that I truly wish to work for myself, it is the perfect opportunity for me to make a change. My risk is making the move from the steady, albeit low-paying, position to ultimately functioning as a independent financial advisor/consultant. In the meantime, I’d like to gain experience in other areas of the industry to learn about what opportunities exist (i.e. I don’t even know what I don’t know… the worst of all possible worlds).

    This article hit the nail on the head about how most of us (especially me) are programmed to be extremely risk averse. It is important to recognize the difference between making a career move and a life or death situation. Nothing (well almost nothing) is worse than feeling static in your current position with seemingly no inertia to propel you forward. It’s great to read articles like this so you can reevaluate your situation and see the forest from the trees. Thanks for the motivation.

  48. I’m actually working on taking a risk right now. My day job is in engineering. Like this post explained, I’ve finally woken up to the fact that this job is in no way secure. Downsizing, outsourcing, and general market trends has led me to try a venture out for myself.

    A year and a half ago I decided to develop one of the many ideas I’ve written down over the years. It is a product for the pet market – a cat hammock for cat owners living in urban areas or apartments ( Just putting the product out there in public and opening myself up to criticism was a large step. Would people reject it as stupid or a bad idea? Would I loose all the money I spent getting it going? I decided I had to take that chance and give it a shot. I went through many prototypes and traveled solo to China to attend one of the largest trade shows in the world to find manufacturers. The cost to start things up was around $8k which while it isn’t an earth shattering amount of money, was still a decent hunk of cash to drop on a project. The launch of the product is coming soon and so far the response has been phenomenal. Blogs and other websites are covering it without me calling/begging for write-ups. Distributors in other countries are e-mailing asking to sell it and local companies are asking for pricing and availability. So far it is going great.

    Starting this project I had hopes of earning some money on the side with some dreams of selling enough to quit my job. Quitting seems like more of a reality every day now.

    Looking back, taking that “chance” to put my ideas out there on the internet and give it a go was one of the best things I’ve ever done. The confidence boost is amazing and the learning opportunities are endless. I’m looking forward to the future!

  49. I’m 29, married and have 2 little girls. I have been a 100% commission, employee benefit specialist for almost 5 years and I am so bored and unfulfilled with what I do for a living. A friend of mine started an IT company last year, specializing in cloud, monitoring and managed services. He asked if I wanted to be his account executive. I know nothing about IT but know a ton about building relationships, etc. I thought it over and decided to give it a go.

    I am being paid to learn ($350/month), so money is not a motivating factor. The risk involved is that the more I learn, the more excited I get about their company and eager I am to go full steam ahead, and I cannot focus on doing my regular job, which I need to support my family. And his company does not have the revenue to pay me even “part time.”

    I want to push forward with the lack of experience, hustle, energy and willingness to learn because I see the potential to move my career to another level and position myelf to where I am providing solutions to people instead of just selling products so I can make a buck.

    Thanks for the encouragement.

    Cheers, Michael

  50. Hi I’m Shawn, 19 year old hacker and musician living in Los Angeles. So far I’ve been hacking my way through life. Literally. For example, hacking my high school before quitting.

    To start off with a short background, I bootsrapped a side project / hobby which sells software in over 50 countries. I love making inspiring videos, I love making music and playing gigs, and I love creating value that will make an impact in the world.

    In the next 30-60 days, the risk and change I have been working my ass off for, is to create a ground breaking information product for founders, bootstrappers, and hackers that will be nothing like anyone’s seen before. So awesome in fact, that people will not be able to resist sharing it and writing about it everywhere in blogs and the press. 🙂 I won’t sleep until that happens… and I will hit roadblocks but I will iterate on feedback and make it happen one way or another.

    I want to also continue designing and collaborating on one of my longer term startups that will shift constellations in the email space. This will require risk of putting myself out there using extremely creative ways to get certain people’s attention, like Kevin Rose and getting the resources I need for such a venture.

    I also want to continue with a potential deal of raising around a million for this tech startup of mine even though I have never raised money before so I definitely have a fair amount of “im scared shitless” with uncertainty and failure to anticipate, so it’s written all over with risk. I expect great things either way… but did I mention I’m still 19 fuckin years old? Anyway, I am willing to fall through. I will manage by getting my lifestyle as ideal as possible, workout out, drinking tea (of course), eating choices, personal development… all the stuff that goes along with that.

    Tim, if your reading, want to of course mention that I am big fan of your work and appreciative to all the value you bring to startups. Thank you!



  51. “A Word to the Wise Ain’t Necessary, it’s the stupid ones that need the advice!!”

    Bill Cosby

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

    I strive to learn, start up and build a company from the ground up that will produce a profit while contributing to youth sports program on a global level. (Much like the business model of TOMS shoes). This opportunity will not only enable me to live financially free and but also help young athletes around the globe gain direction, camaraderie, and a sense of importance and confidence to succeed in life.

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

    I try not to…….

  52. Call me Ruben. Here’s my story. When I was nine I read “rich dad poor dad” and understand for the first time that education sucks. It interferes with my learning. I wanted to quit school and become an entrepreneur but my mother didn’t let me and I expressed my anger singing Pink Floyd’s “the wall” all time long. Nevertheless I started my own business selling brownies and candies but decided it was not fancy enough and at eleven years I begun importing electronics and selling them on Mercadolibre (Ebay’s equivalent for Latin America). It was good money until I lost it all to nigerian scammers promising me wholesale iPods cheaper than production costs. Call me stupid.

    All that time also I was reading books about business, investing, finances, and specially the stock market. I bought Ecopetrol stocks and hit it big until a few years later when I gave some of the money to my father in order to pay a debt he had. With the rest of money I went on vagabonding across Peru and Ecuador for over a month and a half. I returned poor but happy.

    Looking for other alternatives to win money earlier in my teen years I was lured by the promises of internet marketing. I learned adwords, some basic programming in html, how to use autoresponders, how to create sales pages and stuff like that. The result is have a membership site in which people can learn harmonica lessons in videos. Also I made a webpage for one the family business and I’m using my internet knowledge I am able to get new clients and that makes me proud.

    Now I’m 21 years old, in college and about to obtain a bachelor’s degree in biology. My mother almost fainted when I told her I was not going to study economics. I’ve always had a scientific mind and a passion for nature. I envision myself as an explorer and world class expert in biodiversity, working in tropical countries like my own and advancing the natural history of species. My ideal lifestyle is what Tim defines as the new rich, being highly mobile and with a high relative income.

    My career path has risks associated with uncertainties because it is unconventional. But I’m determined to work for it. I have read Michael Ellseberg “The education of millionaires” and off course “The start-up of you”. I’m following recommendations and have my own blog and starting to build my connection capital. I understand I’m a business on my own. I would love your coaching to build a remarkable career.

  53. I am about to take several huge risks in the next few weeks.

    My wife is about to start a new job which will require us to move. I will quit my current, full-time, salaried engineering job and start working full time for my two startups, ModelVP and VGC Unlimited. ModelVP’s first product launches in late July, and VGC Unlimited’s first product is just getting underway, and will launch later in the fall.

    I really didn’t like my engineering job; so, I am extremely excited to be doing all of this, but the nerves are definitely going to tingle for a while.

  54. Where to begin?

    First of all, thank you for this post. An excellent read, and my first foray into the FHWW site (I was refered by a friend, as I am at a point right now where direction would be much appreciated!) Suffice it to say, I will be trolling these posts for a while yet.

    Now, without getting TOO in depth, here is my current situation:

    – 30 yr old Canadian working for Canadian Immigration, with the settlement of refugees in Canada.

    – Recently returned from a 7 month-long self-funded voluntary contract position with the United Nations High Commissioner for Refugees (UNHCR) in New Delhi, India. An amazing experience, and while it has put me back somewhat financially, something I would do again in a heart beat

    – I have been a volunteer with the Canadian Red Cross in Disaster Management for the last 4 years, and I love it. It has allowed me to deploy for small and large scale disaster responses, and to be able to help those displaced and at a low point in life.

    – Wanting to finally gain PAID work overseas with an international aid organization working with both refugees and disaster management, I have found my two, two-year technical diplomas are a hinderance, and my lack of higher education is a disability.

    So, I have enrolled in an MBA program in Geneva, Switzerland for the fall. This program is an MBA which focuses on International Organizations (think UN and International Committee of the Red Cross). Exactly where I want to go, to do this work on a larger scale.

    However, Geneva is super expensive, as is the program. Finding funding has been a problem, and I am at the cross-roads as to whether this program (and it’s massive price tag) is:

    – Monetarily worth it

    – Future-prospect-wise worth it

    – The best choice for a graduate program

    My conclusion? Uncertain.

    I have a steady, if not sometimes boring, job with the government. I have debt still from the above mentioned self-funded Indian volunteer experience. I also own a home here in Canada that was hit (not super hard, but hit none the less) by the recession. Basically, this is the worse possible moment financially to pursue this.

    With D-Day looming (Mid August) and a decision to be made, I could really use some direction. Whether I win the contest or not, I’d love a chat with any of you that may be able to shed some light, and help out a wannabe international aid worker!

    Thanks for listening, and thanks again for the article!


  55. Tim,

    Thank you! Thank you! Thank you! This is extremely timely as i am contemplating leaving the “safety” (LOL) of a full-time corporate job to follow my passion of writing, publishing, and Internet marketing. I’ve had lots of extracurricular’s for the past decade: consulting, website launches, writing 4 books, online products, etc. but never had the balls to make the leap.

    I do agree that my impression of risk is skewed. I see not having a fixed paycheck as close to disastrous as one can imagine. Not steady pay check? How am I going to pay for my kids to go to camp? What about my lease, mortgage? The downward spiral of negativity seems endless. It’s amazing how easy it is to forget that I’m a smart guy who leaned how to navigation corporate BS for 15 years – I think I’m pretty resourceful when I need to be.

    I think that the unknown is what creates fear. When you don’t have a specific goal in mind – or a clear plan for getting there- one tends to have doubt, experience anxiety, and back away from the ledge I guess that’s why its so important to choose your friends and mentors carefully. They can be the voice of reason in an uncertain time and help mitigate the risk you think you’re facing.

    Thanks again for sharing such great information. I’m sure I’ll be making a change soon and although it’s filled with uncertainty, I know I’ll find the path to more freedom, satisfaction, and maybe even security!


  56. My name is R.J. I’m 27. I manage a division of an independent insurance agency, a family business.

    In the next 30-60 days, I’m looking to add someone new to my team, although this will cut my salary and essentially make my department operate without profit initially.

    Short-term this will provide better service to our current customers, due to the volatile insurance market, we’re doing much more service work then before. As of right now, we’re behind and losing good clients.

    Long-term, it will allow me to work more on my business, rather then in my business. My strength is in sales and marketing.

    The risks…

    I’ve never hired anyone outside of our organization. Will I be good at it? Would if I hire someone, that’s a total flop?

    I have my first kid due in the next few weeks, not exactly the time I need to be decreasing my own salary.

    What happens if I do nothing? We continue to operate at a profit, although steadily shrinking. But then again, maybe the market flattens out, and now we’re over staffed.

    A few insights from just writing this down:

    – A new hire is financed over 12 months. A total flop, if I catch it early, doesn’t cost me that much.

    – I have a full emergency fund. The purpose for creating it was for me to take more risks in the first place. It’s funny how quick I forget that.

  57. Hey, guys, what a great opportunity you are giving us. Like you, Reid, I’m a mid-40 something and I just quit as VP at one of the “too big to fail” banks in order to return to a previous gig to manage their BI group and work with some cool technology. But that’s to pay the bills. My real passion is education, and I want to get a masters in Mind, Brain and Education @ Harvard in order to teach kids and adults how to maximize their learning potential. Risks: opportunity costs ($$$), leaving my wife and kids for part of the week to travel to Boston for school, and not knowing what my income or career will look like after getting the degree. Looking forward to your advice!

  58. No more cubicles and 9-5. The pursuit of an acting career. Sprinkled with health and fitness advocacy and entrepreneurship. The transformation has begun.

    After roles in technology sales and healthcare software sales, I considered joining the startup, Mashery (phenomenal group of people with a bright future!). It was difficult to turn down, but I decided I wanted to exit the sales world for now.

    I will be adventuring into the world of acting. I used to act when I was younger, but purely recreation. I have now decided to full throttle pursue it as a career. I had the internal dialogue where I realized if I was 45 looking back on my life and I never gave acting 210% effort, I would regret it. I don’t regret, I do. I would prefer falling on my face and failing, over never knowing. I will be moving to Los Angeles in 9 months and getting as much acting experience as I can leading up to.

    The sprinkles enter here: I am currently beginning a store management position with the athletic apparel company, lululemon. Retail, you say? Think again! Yes, lululemon sells athletic clothing. But that is simply how they operate a much larger operation: increasing the physical and mental wellness of locations all across the world to create healthier, more connected communities. Beyond storytelling through acting, my passion is invigorating people for a healthy world. All while getting more and more folks outside of ‘cube land.’

    The risk is and was all artificial: financial, ego, reputation, and fear based. I am taking a huge pay cut, less job stability, leaving the ” high tech world to go into retail” (as many people said to me), or even better, “entertainment which has the odds of the NFL for success.” I will gladly live within a new level of means in exchange for pursuing my dream. My ego is just another impulse that I’ve learned to be mindful of, as is fear. The only true risk is never going for my dream in this nonrenewable time we have on earth. As Steve Jobs said, “everything else is secondary.”

    My name is Brandon Wardle and I live in Boston. Venture – Adapt – Innovate: It’s what I stand for. The words of my favorite acting coach, Larry Moss, sum up who I am and the change I want to make: “That’s what our work [acting] can do: we remind people that things can change, that wounds can heal, that people can be forgiven, and that closed hearts can open again.”

    Thank you Tim, Ben, and Reid!! Fantastic post!

    Be remarkable,


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

    After 5 years of climbing as fast as I could in terms of salary in full-time positions, trying to raise two young children in L.A., starting as a 26-year-old guy in law school and parking cars (I quit law school because I hated it, and have now been trying to outrun the loans! :), I may finally have the chance to break out of the 9-5 trap and work remotely full-time, for clients as well as my own startup, while still (if all goes well) making enough money to keep my family afloat, although not much left over to invest in anything for the future.

    I’ll know more in the next couple of days, but in a nutshell: I have built up a solid client base on the side (digital marketing) and may soon have an opportunity to work part-time, remotely for an agency and thus quit my full-time job.

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

    As mentioned above, I have a lot of responsibility on my shoulders as a now 30-year-old with two children under the age of five, and expenses that are only going to go up as they get older (ie. school).

    As with every move I’ve made in the last five years, my decisions and effort have all been geared towards maximizing their security, with all of my remaining effort focused on creating the personal freedom I want for myself. I have managed to build as much of a safety net as one can build in these crazy times, will hopefully soon be able to transition into remote work (step 1 of personal freedom), and then from there pivot to continuing to grow my social utility/network for parents and other business ideas.

  60. Hi, my name is Lily. I used to be one of those government workers you described in your post, but the monotony and predictability of the job was eating away at me; I actually need more risk and uncertainty in life! I recently married and, with my husband’s support, have left the government job to begin a career that will match our very mobile lifestyle.

    Inspired by the 4HWW and Tim and Stephen Key’s blog posts on licensing, I came up with a product idea–something that will work well for people who travel by RV with their cats and small dogs (as my husband and I do)–and in the next 30-60 days, I will be submitting a provisional patent application to the US Patent Office, contacting manufacturers, and

    negotiating a contract with at least one of them. I have been running a marketing test on the product with some promising results!

    Financially, I will only have invested a few hundred dollars into this business, so if it turns out to be a dud, the losses will not be great. When thinking about the risk involved, I prefer to think about the potential wins (a regular royalty check!) and the risk/lost opportunity of NOT pursuing this idea. Possibly the hardest part of this for me is that this is my first ever undertaking of this kind, and I am learning everything from scratch. I fear people may not like my invention as much as I think they will, or that the manufacturers will think it is a bad idea and be uninterested in making a licensing deal with me, or that I will goof up and say something stupid while trying to make contact with the right people in the manufacturing companies. However, I also realize that the more calls I make, the easier it will become, and next time I do this, I will have a better idea of what to expect! In time, my efforts may free up my husband and me to truly live the lifestyle of the “New Rich” that Tim talks about in the 4HWW. That is my aim!

  61. I’ve learned the difference between gambling and risking, “taking a chance on the unknown….”

    When I take chance on the unknown with my own resources, I become open to tasks at hand instead of images of past or future success. And to people who want to move in the same direction.

    My work history moves from bookstore management to forklift driving, to Parcourse fabrication and installation, to publications management in an 80’s Silicon Valley startup, to starting the Logitech Publications Group, to journalism and conference moderating in the Virtual Reality field, to managing the Cygnus Solutions Publications Group, to working on a library database project in a Greek monastery, and a contract as “Corporate Poet” in a VR startup in Seattle.

    Now suddenly I remember the evening dinner break at Planter’s Peanuts when I was sitting by myself reading some book or other.

    Jose Sanchez, one of the other forklift drivers, had lost at cards with the other forklift drivers and walked over to my table.

    I was a kid of 33 or so, and he was an old man of 38.

    Pointing down at me he said:

    “Kid! In this life you gotta be crazy and you gotta know the business!

    “If you’re just crazy, you go off on a trip somewhere and nothing gets done.

    If you just know the business, what’s the difference between you and a stone?

    “But if you’re crazy AND you know the business, you’ll do alright….”

    In his honor, I call this The Jose Sanchez Principle.

    Today I ask myself again, “What do I want, right now!”

    I want to work with someone who can work with me to code the interfaces I design for my web site, and for an iPhone/iPod Touch app that has three phases:

    the first, free and entertaining but useful,

    the second, a little more interesting, possibly with a small fee, and

    the third, to be sold to a specific web presence.

    That established, I hope to work on even more useful and usable projects.

  62. Hello,

    My name is Michael Clark. Risk as been my friend and enemy my whole life.

    I grow up in the Boston Housing Projects, where the biggest goal for my friends was to work at the warehouse down the street or for the local drug dealer. Neither one of my parents graduated High School and worked in the cleaning industry. I never knew I was poor really, until I tried to apply to College. That takes money, but I was lucky. A small college in Newton Mass, just went coed after being a all girls school for decades. They needed boys to start coming in and something I found out later was they needed black boys more. The goverment was giving them big grants for doing so. So when I applied I guess being from the “Projects” and also willing to try out for there new men’s basketball team meant I was a perfect fit for them. So for a 15K tuition they gave me 14.5K in grants and loans, with only a few phones calls but mainly SIGHT UNSEEN!

    The first day I walked into the bursers office and told them who I was, they didn’t believe me. If fact they really gave me a hard time until someone told me the truth “Off the record”, they thought I was black. I guess most of the grants and loans where under this premise. Well it all worked out, they where so embarrassed that they just changed all the names of the loans and let me in. They also told me that I wouldn’t have gotten in any other way which I thought was nice of them.

    I knew this was a great break for me, so I took full advantage of it. I worked my ass off and got A’s and B’s. Over coming peoples perception and succeeding is part of my life. Being a project kid you are always told your not enough. I have seen alot of my old friends never leave the streets they grow up on and still doing the same old same. Going to College was a huge thing in my hood. My next step of getting a job. Growing up in the projects really did prepare me for college, the job market and the corporate world. Like your articles states small daily risks prepare you for bigger ones. There where plenty of risks in the projects, but I was surprised by how much I missed the place when I left. I wanted to trade for the devil that I knew for the devil that I didn’t. Risks come in all sharps and sizes. Like you said what is a risk one is not such a big deal to someone else. Leaving the projects was a big deal for me. Leaving College for the working world was a big deal to me. Overcoming insecurities of being a ex-project kid in the corporate world was a huge deal for me. Buying my own home that wasn’t attached to anything was a huge deal for me. The decade or so it took me to realized that I was good enough to start my own business was a really really, huge deal for me.

    So now the story ends or rather begans here. I am 8 months into running my own Product marketing, branding and packaging design firm called Shelf Identity. I have 16 years experience in 3 fortune 70 companies as a art director/Designer/Manager. I am a proven surviver and adapter with great untapped and tapped talent and would love to work with people with fresh, new ideas.

  63. I’ve applied a lot of this methodology in my career. And interestingly enough, I’ve watched a friend concerned with stability work at the same manufacturing plant he worked in to get through college after he graduated. And, he still has the same income.

    I wanted to make my job experience serve me to gain skills I’d need to become an entrepreneur. So I started by taking a job in Sales. I learned lots about conversation control, spin selling, and more. Eventually I got tired of that and decided I would need to learn to scale sales messages from 1 – 1 to 1 – many.

    So, with no experience, I went off to look for jobs in SEO, so I could learn to drive traffic to websites. I read as much as I could on the subject, pirated information products, and got myself a strong knowledge base in the subject. From there I wrote a terrible resume and threw it out there. I got some interviews & with each interview I adjusted my resume to reflect the recruiters perception of important skills and employee traits.

    Soon I landed a job in SEO, and learned about the importance of customer development and achieving product market fit for startups. I got fanatic about learning everything I could about product market fit and customer development reading books by Steve Blank and other lean startup advocates.

    I realized if I want to get good at starting & growing businesses I’d need practice doing that. So I pivoted away from SEO and into conversion rate optimization to learn how to split test & increase revenue for web business.

    Through out this journey I’ve “lied” my way into a couple jobs and been fired, learning a TON in the process. I’ve taken low paying jobs where I’d e able to learn a lot (that’s how I go into SEO). And I’ve always worked on side projects in the evening on my own time to help me learn and develop news and useful skillls.

    I’ve been able to double my salary for stints of time, while I’ve watched my friend recieve a dollar per hour increase each year. I’ve been able to increase my income from working drastically with each new job I take, while my friend debates the prospect of seeking a news job. I’ve developed skills that will help me when one of my side projects strikes a responsive chord, while my friend, should there by a disruption in his industry will find it hard to deal with the fall out. I love my friend, just being honest about what I see happening.

  64. This is the perfect article after returning from a 10-month trip around the world. My wife and I sold and left everything and had the time of our lives.

    I graduated with an MS in Engineering from UC Berkeley and worked in NYC as a consultant for big pharma in the Latin American markets. I took a risk and left a well-paying “safe” job to start my own business in SF while doing engineering research at UC Berkeley. Business was good and research fine but I wanted to explore the world. I took a risk and left research. I applied the 4-hour work week on my business and left everything to enjoy the world.

    We came back with the same net worth as when we left thanks to the business and we had a plethora of priceless experiences. The risk more than paid off and now I’ve been to 20 countries and met lots of wonderful people.

    I returned 2 days ago and in deciding what to do next it’s great to look at risk vs. opportunity. Unfortunately, it’s still difficult for me to turn away from the “safe”/low-volatility options but now I know why, because of evolution and it makes perfect sense. I’m deciding between going back to research, applying to corporate jobs with business development, or start my own company. My preference would be start my own company and I already have two ideas (one is already profitable but needs to scale and the other one is in its infancy but with lots of potential). My hesitation includes: unstable income, “what if it doesn’t work?”, risk missing out from current earning potential ($100k/yr+ on a corporate job), etc. However, the opportunities include freedom, work something I’m passionate about, create impact faster, wear many hats, etc.

    I consider myself a person with passion and capable of anything, yet I hold myself back at times due to something I did not understand. As I continue to move forward and think about my next move, I will remember that we humans tend to give a higher priority to risks and un-“safe” moves due to evolution. If I keep this in mind, I might be able to be less risk-averse and shake some things up and create impact not only in my life but in projects I’m involved with.

    Thanks for the great article and I hope to meet you soon.



  65. HI, My name is Damian, I leave in Poland, Europe.

    I work for Google, but i want to leave this comfort zone. You can ask: “Why?”

    I want something different. I want to take a challenge and risk without fear.

    The reason is, I feel I want to work for some small company, where I can have bigger impact on daily improvement and business creation. I believe, that with my passion I can achieve more and help people improve their businesses. It’s a a hard decision, but as a Steve Jobs fan “I need to follow my intuition or karma – they already know, what I truly want to become”.

    Next month I join small company Paylane in Poland as a new business developer. The challenge is:

    1. I have never worked in B2B sales, but I extremely love people, presenting ideas and new technologies, which make business easier, so than can be very helpful.

    2. The company wants to explore USA and Europe being based in Poland, which still can be difficult.

    When it goes to Risk I see some point:

    1. My salary depends on results, so I don’t have any financial security at the beginning

    2. Maybe I can realize in some point, that I don’t match to sales because it is harder than I expect and I will stuck in some point.

    3. For small polish company with low experience on international markets it can be very challenging.

    I believe although in this opportunity; I will earn less at the beginning, but with the time i hope i will increase my knowledge, network, understanding of business and personal engagement. I hope that with your help and mentoring I could start building my business network in USA and tell the story of our innovative idea.

    I will follow the quotation from Tim Ferris book: “Doing impossible is easier than doing possible”.

    1. @Damien, you hit the nail on the head with respect to the risk of working a big company. Oftentimes, professional growth is slower, individual impact smaller.

  66. I am in my mid-thirties and for the last ten years have followed my passion in politics and government. I have had successes, failures; opportunities, and missed opportunities. Overall, I do fairly well, can support my family, and could coast toward a lifetime career in this field if I chose to.

    But I need a change.

    No, I HAVE to change.

    At my core, I am a creator. I think we all are. I have passions, ideas, and a multitude of dreams I would like to accomplish in my life. I’m writing two books — comedies. I want to start non-profits on issues I care about deeply. I want to start a radio station.

    But my biggest dream is launching a tech company. I’ve been drawn to tech since I was a little boy. I don’t remember this, but my parents recently told me how I took apart their tape recorder and fixed it when I was five or six, so some fundamental part of me has always been drawn to the way things work.

    In recent years, I seem to be going back to these roots. I am learning to code, learning design, dabbling in hardware. And along the way I’ve come up with an idea for a tech company that I have fallen in love with.

    To get this idea off the ground, I have spent all our savings and nearly maxed out credit cards. I have a decent demo now, although it will take some more work to take it live. I am well-aware that the odds are stacked against me. I am not an engineer and I’m 100 miles away from Silicon Valley. However, there is no doubt that I need help taking this company to the next level. Your advice and mentorship would be invaluable! Thanks for considering.

    And I believe in paying back and paying forward. Once I find success in this dream, I want to mentor others by giving them the tools they need to achieve their dreams. In that sense, you and I have something in common!

  67. On June 1st I gave myself a goal, change my career in 60 days, no matter what. Even if it means quitting my job without a new one on July 31st. New career. No matter what. 

    I’ve spent the last 12 years working for banks. 2 years ago I got laid off during a merger and even though I wanted something different, and I had plenty of time to find something different (Yea layoff packages!) I still took the “safe” route and took a job at a rival bank.

     Now, two soul crushing years later, I’ve had enough and it’s sink or swim time. For to long I let the “But I won’t make enough money there!” mantra hold me back.  Even now it’s scaring the crap out of me, but it’s driven me to re-evaluate what I really need to survive, what my real “worst case” might be, and frankly, it not that bad. 

    My net worth is a positive number, not a big one, but I’m not upside down. If I had to sell all of my stuff, I could zero out my debt. I might have to start renting an apartment, rather than own a nice house, but it would be doable, my wife would support my decision(she went freelance 4 years ago).

    So. The applications have been going out. So far mostly to local non-profits I’m already working with that happen to have openings right after I started looking, but it’s a start, and one way or another I’m not going to have my current job much longer. 

    Having a mentor would be pretty handy. 


  68. My risk is to completely change focuses into a new career in startups to eventually start one of my own. Short term goal would be to network like crazy, go to meetups, and hopefully try to get involved in a startup of interest where I can develop skills there and on my own. The risks would be time sacrificed to learn, income made doing something else, and loss of “freshness” as a relatively new graduate. Coming from a Biochemistry background, I have zero experience in coding, marketing/ business work, and also, little knowledge about the tech/startup industry (right now). I was pursuing my degree in vain, and it took traveling to Asia and getting a new outlook on life, as well as, articles and sites like these, to give me the courage and support I needed to make the change despite discouragements around me.

  69. Currently I have no career, I am 18. In the next 60 days I could go to university or I could try starting my own company, I am trying to decide what to do.

    I could go to university, but I find that each day I have less and less passion for the course I am taking. I don’t want to be stuck in a crappy job having not taken a degree. But neither do I want a ‘normal’ job requiring a four year education.

    I could start a niche business in the coming months, It could fail and I could be left penniless. However I thought “Is it realistically possible to fail if I follow common sense and understand business?”. No, it’s very unlikely that with my business being small and only costing £200 to start up that it really wouldn’t fail. So I asked myself “Why haven’t I started it?”.

    Fear. Fear that I could’ve spent my time doing something useful toward University or enjoying my life. Fear that I won’t be able to support myself if I fail. But on that basis of that “Shouldn’t you be fearful of everyday life?”. Their are so many situations where you could be killed on a daily basis yet we shrug it off as though it’s low risk. Crossing the road, having a shower, you could slip and break your neck, killing yourself. Yet we still do it and think of it as low risk. You could be clean or dead, Hmmmm…….”I think I’ll take clean!”. I want to have a similar attitude towards starting a business, yet my emotions make it very difficult.

    In the next 60 days I have to make a decision. You would’ve thought that since I’ve been on a 4 week expedition to Iceland that I could handle risk, but I am still undecided on what to do.

    Even if I don’t get the chance to email Reid and Ben, I would appriciate some advice from other people reading this, I think a different perspective would help. Many Thanks

  70. I’m going to jump ship again on July 7th.

    I spent my life training and made it to my dream job at NASA designing rockets – but they we’re going to build ’em so I resigned from NASA in 2009 giving up the high pay civil service job! I moved my family to New Zealand to a house on the beach to think for a bit – ended up running a boat building company for a year (stuff got built – kiwi’s can build boats) – then I quit to think for a bit more. I’ve started a consulting company to provide energy analysis for homes – and try to change how homes are built – pays the bills but I’m working by the hour again.


    July 7th I’m going to take my son (he’s 4 now) and go back to my hometown of Fitchburg, Massachusetts. The last stop on the commuter rail from Boston: I’m going to start a company not a job. I’ve cash for four months and I need to be able to be both in New Zealand and the USA.


    This is it for my cash – if I fail I’m broke (I do have a round trip back to the south pacific paradise of New Zealand).

    My wife could leave me while I’m gone for four months.

    My current consulting clients might ditch me so I’ll have to work any crap job back in NZ to feed my kid.

    BIG RISK – my ideas will suck and I won’t make any good contacts totally wasting my time in the USA.

    I’ll start a company – dump in my time and IRA and fail – when I could’ve worked as a consultant and relaxed and kept those funds.

  71. Hi,

    The change I would like to make, in the next 60-90 days, is to help my friend Clark move his startup one step closer to his goal by leveraging your experience and industry contacts. Here is an email he sent to his friends and family on June 13th describing the risk he is currently taking:

    Friends and Family-

    I think I’m going on almost 6 months since my last update so I thought the timing was appropriate for this email.. Especially considering it has been nearly 1 year since I left AMS. Wow! Time flies when you’re working 15 hour days…

    To begin, I will answer many of your questions with this simple statement.. life as an entrepreneur is BY FAR the most challenging thing I have ever tried to accomplish.

    Here are the joys awaiting anyone interested in following my path:

    · I still don’t have a car.. it may seem like a novel approach to keeping healthy but many of my neighbors are wonder why I’ve become super eco friendly as they see me walking around town.

    · The sun light hurts my eyes.. too bad a computer monitor doesn’t give you a tan or prepare you for the outdoors..

    · I haven’t seen my friends in a while.. not because I don’t like you but it’s almost impossible to leave my office when there is so much to do.

    So in summary, startups don’t pay.. save up your money before you make the jump, get ready to max out your credit cards, and enjoy the entrepreneur diet of bread and water!

    But… with all the challenges and daily difficulties I LOOOOOVE it!

    The things we are working on at (I deleted his company name) are awesome and truly inspiring. I can honestly say I’m pumped up each morning when I think about its potential……

    Enter Kevin:

    The email goes onto talk about personal goals that I will keep private.

    Thank you for your time.


  72. My name is Joshua,

    I’m 20 years old and am getting married at the end of this month. I’m commenting from a Starbucks on my work phone (an android) that was given to me by my newly acquired job, Telus Mobility in BC Canada. This is my “learning experience” period you described in the post. My five year plan ends with me working from some far off country on a mobile device (an iPhone) with no bosses or managers calling me in to build a paycheck that barely makes it to me after payroll. I finished Tim’s book the summer I turned 19 and finished my firstj start-up two months after. Onebuyandsell – a completely outsourced project inspired by 4HWW and the connection I made with’s CFO Paul English (a connection also inspired by 4HWW) – was my first jab at financial freedom and the life of the new rich. After experiencing the blow of cruel reality that Onebuyandsell would not be the project that draws me my $40,000 a month – and realizing that a 19 year old with no secondary schooling cutting lawns during the week and singing in a rock band on the weekends isn’t particularly what Twitter, Facebook or Dropbox are looking for in their next product development expert – I decided it was time I got a little practical. Thus leading me to a family connection with the president of a local Telus-authorized dealer. Now I’m furiously engulfing as much sales experience and information as possible in hopes of someday employing guys like me. I need coaching to help me filter through the ideas I have and manage the full-time sales job with a part time start-up that’s going to take me out of the rat race and into the lifestyle of the new rich.



  73. What change do I want to make in my career in the next 30-60 days? For someone that is married with 2 kids (3 yrs and 1 month) change can be hard. That said, change must happen. We must evolve. I liken it to the Dr. Suess book “Oh, the places you’ll go” where it talks about ‘The Waiting Place.’ If you don’t change you’ll grow stagnant and always wonder. You’ll be stuck in the Waiting Place.

    Working in college athletics most of my friends think I have it pretty good. I’m working a job at my alma mater that many would drop everything for. It has a ton of upside but something is missing. You talk about risk earlier. There’s not a lot of risk here. It’s government work. Albeit, fun government work (I know, kind of a oxymoron). I could make a career here and be perfectly happy but I can’t help but think something is missing. Public versus private sector work is VERY different and there are times that I long to get back in the private sector. A place where deadlines and innovation are commonplace. Where creativity is encouraged. The last 5 years have not seen any of those things. I have made my way up the chain by taking some risks and now is the time to look at taking another one.

    Over the next few months, 1 of 3 is going things to happen, depending on how the dominos fall

    1.) I will either be taking on an entirely new role at my current job – going from fundraiser/project manager to Director of Marketing

    2.) Changing Universities to progress in my career, possibly moving into professional sports

    3.) Or, changing professions entirely and pursuing something that is totally new, consulting while working towards building my own start-up.

    Clearly, the later of these is the most risky, but all will present challenges. We’ll see how it goes.

  74. – 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?

    My name is Lisa Ann, I have been in the wedding industry for over 20 years. I was one of those rare photographers who went digital way before it became common. I have also been the photographer who enjoys working with the middle market bride over the high end clientele.

    I bought a laptop within the first year of going digital and quickly found my potential customers were not looking at the ‘photography’ in the hundreds of images that scrolled across the screen, but instead were looking at the ‘content’. Statements like; Where did that dress come from? Who was the cake maker? That is a really cool vest on the groom. What is the type of cloth are those linens are made of? I made the mental note to learn who all the vendors were at every wedding I was photographing so that I could answer those questions.

    In 2011 I launched a web site with the goal of connecting local wedding vendors with brides. I want to take this data based web site national. We gave away 10 photography packages throughout America with the goal of gaining insight on how REAL brides plan and implement their weddings. (This has been an interesting and thrilling experiment.) The way we want to expand the website and now online magazine is to document a real wedding in every state in less than 80 weeks of time!

    The goal is also to provide useful information about planning a wedding within the region that the bride lives in by publishing articles with local professionals being written about or asked for industry education tips that are important to that market. Weddings do differ from state to state and budget levels. There are so many regional customs, religious traditions, and budget considerations that the big national industry can’t cover – which we can.

    How does this tie back to photography? Brides love images and are inspired by them. Pinterest and Facebook rely on people’s love of images. Our idea…mix images that are captured at real weddings and not staged for articles with all the content and vendor information tied to the images themselves plus add them to the love stories of the couples getting married.

    Next step? Invite professional photographers nationwide to jump on board and provide images and stories about the weddings they are covering.

    Next 30-60 days?

    I want to finish the business and financial plan for my existing company. I then want to take the risk of finding a primary investment partner to enable the project to move forward. The goal is to finish building the web site, integrate the ability for nationwide photographers to share their wedding experiences, and to launch the 80 week national tour promoting the website/magazine in every state.

    The risk involves two primary factors:

    1.Sharing ownership of the company (is always a risky factor in my mind.)

    2.The risk of having the primary vision for the company shift because of an outside influence.

  75. What a great blog post – always value-packed with unconventionality and insight from the most inspiring minds!

    It’s great timing – I am currently working with my business coach on making yet another transformation in my career. I am currently the top salesperson for the largest restaurant franchise development company. After reading the 4-Hour Work Week, it allowed me to automate, delegate, eliminate, and liberate my sales career to where I am now the only 1 in the company who works remotely, gets to travel to the likes of Asia in the MIddle East, focus on the highest-yielding deals, and do what I want to do.

    During the economic downturn and salespeople were either quitting because they didn’t have faith in our company, or when underperformers were being laid off – I believed in the company and my own abilities – and so I took the biggest risk of all. I asked to eliminate my base pay. It was unconventional and a total paradigm shift; it surprised my company executives, but they agreed to it, believing that the risk got shifted to me. But you’re right – although going on straight commission may seem scary and uncertain, I didn’t overestimate the risks (it was in my control, I negotiated it so that the yield would be substantially higher); I believed in my self, abilities, and resources (I didn’t fall victim to underestimating my resources); and now, even though the company has recovered, I have no interest in going back to the original pay scale. I control my time better, work remotely wherever I want, and I make substantially more money. Power to the right way to manage risk and take opportunities!

    Although I have a pretty good path on how to manage my career, your insights were amazing, I can continue to learn/strengthen myself, and I would love to be surrounded by Tim and you guys. In any case, reading the post was a prize in itself. Keep it up, Guys. You’re changing my life and others’!

  76. Hi – my name is Matt, I’m 38 and based in Australia. I sold a stake in a consulting business a couple of years ago and after travelling and toying with a range of options (which has been great fun) its time to get serious – so the change I want to make is to commit to a specific project.

    I like the risk/opportunity adversity balance you highlight; for me, I’m thinking much more about the risk of not doing something (or just spinning my wheels) and about how to navigate the many opportunities I see to choose just one (or a handful).

    Thanks for the blog and book, its thought provoking and confronting stuff and I’m up for the challenge!

  77. Awesome Post!

    My husband and I read Tim Ferris’ 4 Hour Work Week back in November 2011. We made a drastic change and took major risk to go after our dreams. My husband quit his job of 11 years – with barely any money in the bank – sold our stuff to survive and renovate our condo – sold our condo after 2 months and took our money, bought a ticket to Costa Rica and are now living and travelling here. Thinking back, it was the scariest thing that we lived with such insecurity for those few months but the gains have been enormous. We sort of did it backwards but Tim’s perspective has helped us to really Dream big! My husband is now following the 4HWW and is building a prototype for his first product and we are starting another project together based off of our experience travelling, dream lining and thinking big. It has been the most rewarding experience of our lives to finally face our fears, consider the risks and realizing that the outcome could only be better than being trapped in a life full of debt, stressful and draining jobs and no real hope of happiness. What we didn’t expect though is that the outcome is better than we could even imagine. It is really true – Fortune favours the bold! Dream big and WIN. From living pay check to pay check to living with risk, adventure and challenge everyday – we have decided, it’s the only way to live. Make the uncomfortable = comfortable. 🙂 Now we are living the life of our dreams, doing what we want, building our companies and focusing on personal development and success everyday. We have a beaten and battered copy of 4HWW and it has been with us during all our travels here in CR. We hope to meet Tim one day and thank him for what he has helped us to do – beer is on us! 🙂

  78. Thanks for the article. I’m looking to change jobs now, so this helped. I’m struggling to get employers to recognize skills I’ve built up over the years, including self-employment. My biggest challenge is to get in front of someone who will question what I’ve done so I have the opportunity to explain what I can do.

    I’m older and at the stage of helping a parent, so some of your statements about risk ring true for me. I’d rather take the view of moving into a better position rather than saying that less could mean more. Still I’ll think about what you wrote and see if I can use that to come up with some better strategies. And I’ll look at the books.

    Thanks Tim, et al.!

  79. 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?

    Hello there, my name is William Lust and I am a chiropractor from Wisconsin. I am currently practicing in a satellite clinic for another chiropractor, who wants me to buy him out when we can get busy enough. The thing is we have not been able to be busy enough in the over four years I’ve been here. I’m in social organizations, active in the chamber of commerce, do a weekly senior center exercise classs, tons of ads and mailers, and I feel I adjust well and have a good ‘bed side’ manner with patients but it’s a rural town I live in that has had a lot of industry that’s moved away. The bad economy is apparent, as it probably is all over the country, but I don’t want that to sound like I’m making excuses. I might be, and probably am, but the future of this country, and especially the middle class and the health care system, are not getting better anytime soon. That makes my job harder, because people will only pay for what is desperately necessary and optimal health is not as valued in America as you think it should.

    I have been thinking about taking another associateship in Singapore. What I know so far, from reading the job description, it would pay over twice my current salary and have much greater bonus opportunity, with the marketing done for me, and with much less competition. I would like to normalize myself outside of the US as well. The current state of affairs here is scary, and I want to, not only give myself a chance elsewhere, but to give loved ones a place to go if need be. The timing is good seeing as I am contracted for five years and next May is the end of the fifth year. It would give them time to find a replacement.

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

    It has been a pipe dream until writing it down just now, but the risk is I leave a community, and the immersion value of being a known fixture in the health care-insurance system. I would be walking away from a practice, something I have grown and nurtured for the last four years, which is nothing to sneeze at. It helped me pay off some huge credit card bills. It kept me within a half hour of my Mom and sister; and an hour from my Dad. I was there for a lot of grandparents and other loved ones who just recently passed away. I have been able to keep family close to my life. I would be leaving my home state for an undeterminable amount of time, with hopes of a return back when I’m debt-free.

    The other side of the risk is I stay dependent on a bad, untrustworthy system, get into more debt that I don’t believe I would like to carry, and have things grind along while I end up paying myself last. Or Singapore could be a bust. I could get over there and find it sucks. That the money isn’t any better. Or the cultural differences where too much for my hick mind to handle.

    I honestly don’t want to buy this clinic and get into anymore six-figure debt, so I can say I’m an owner, but with more debt to keep track of. I like the idea of up and doing exactly what I do now, just to a different type of spines. And to be doing it in Asia. And making more. And having more to do. And having it be new and exciting. I feel like I need something different to happen soon.

    I also want to escape the 9-5 and have an internet income so I don’t have to practice. Not having the comforts of home to distract me will give me a better chance at making these next dreams a reality. That’s what the Four Hour Workweek has helped me see. We have more options then we think we do. We just need to get our heads and actions around what must be done.

  80. I’d like to thank you first for the opportunity to spend a little time with the both of you. It would be such a great learning experience to be able to listen and impliment your ideas.

    I’m currently a full-time police officer in Florida and in the next 30-60 days, I want to be able to quit woring off-duty details so I can laser focus my attention to what I feel passionate about doing, which is product licensing. The off-duty work provides the extra money that my family (wife and daughter) need right now but, by its very nature, takes up a lot of my off time. In February of 2013, I’ll be vested with my department which means I can start to draw a pension when I reach age 50.

    I refuse to work one more day after I become vested. Being a police officer wears on you in unimaginable ways. I’ve done my time and I’ve got so much more to offer. Not only to just me, but to my family, my friends and the world! I’m putting these chapters behind me and I’m starting a new book right now. Your help in getting the next chapter in my life started would be very much appreciated.

    The risks associated with my decision are directly related to the security of my pension or what I think is security of my pension and the security of a government job. Everyone else thinks it’s great. They have no idea. The average police officer lives less than five years after they retire. Not me. My family and I have too much to do and too much to see and I know that there’s going to have to be risks taken on my part to accomplish all that I want to do. My wife is a stay at home mom, so it all comes down to me and the risks I’m willing to take. But the risks I’m willing to take aren’t the risks my wife is willing to take. The risks affect us all.

    Thank you sincerely for your time. I look forward to hearing from you soon!

    1. Great comment, Ron. The lure of “secure” pensions really does cause many people to not make a change even though deep down they want to — so a fantastic perspective…

  81. Thanks for another awesome blog! My name is Will, I am 30 and I live in central FL. I was unhappy at my job as a planner for a relocation company. I stumbled onto Tim’s book and three months later I am an independent real estate agent. This post really spoke to me because it is a reallly nerve wracking to give up a garaunteed paycheck to chase the dream of working for myself and gaining more free time. I am still very nervous about the risk I have taken in quitting a secure job, and this blog really confirmed what I’ve been thinking since reading Tim’s book. I’d rather regret taking a risk and not succeeding, than regret being too afraid to try in the first place. Thanks again!!

  82. Hi, I’ve been a trainer, business coach, author and speaker for over 15 years and have developed a great reputation. Much of my business comes in by word of mouth, some of it internationally. I have been looking how i can step back and have decided to develop an internet business which firstly leverages my time and money, until I can then replace it. I love travel and travel a bit at the moment, but would like to seriously increase my time traveling. So, in the next 30 days I am running a free webinar for one of my lists, and I am very nervous as I haven’t done this before. However, I have sent them the email (which has been passed on!!) so I can’t back out. This is the first step of starting to really work and build my lists. Cheers, Shirley

  83. Interesting. Their main thesis is directly contradicted by a Kurzweil web

    site article I read just before this one – that research shows we are hard

    wired towards optimism, and that such an attitude directly encourages the

    recognition of opportunity.

  84. I’ll give this a try. It definitely can’t hurt.

    My name is Jeffrey Collins. I am a painter (fine arts), and one of the big problems I have been dealing with since I decided to make art my life, is where my business is conducted. Columbus, Ohio might be nice for a number of things, but it sure isn’t a big art city. Living here has brought me some accolades. But I have had more big name players in the art world tell me I would do so much better if I were living in NYC, or it’s surrounding areas. I had the opportunity in the best way about 4 years ago when my Father passed away. Died suddenly from a heart attack, once the aftermath came about. My stepmother gave me $18K, and said my Father wanted me to have it to buy a car with, as he knew my 215K mile car wasn’t going to last much longer. Under duress from hearing this, I gave into family thought and purchased a car with that money instead of doing what I had been dreaming about for ten years…moving to New York. I have since had one other chance to have enough funds to be able to move to NY and have at least a few months to be able to shop my painting around before I had to get a job to live with. About two years ago I decided one of the best things to help my career from where I was, would be to make a film where I interviewed all these people I always wanted to meet in person. Kinda like the film PAINTERS PAINTING, where the filmmaker (Emile De Antonio) went around to studios and spent time learning about them and their work. Granted, he was already in NYC and had a crew. I didn’t…but that didn’t stop me. Through the generosity of my Mother, who had recently lost her Father, I was able to get a nice HD camera and sound equipment to make the film with. I began by taking a trip…funded still by Mom, to NH where I interviewed a very well known Curator named Carl Belz. And from there have went on to visit NYC twice and do numerous interviews. I’m looking forward to going back and doing more interviews. But It would be so much nicer if I were able to live there, for just a month or two. But to live there would make it even better. I’ve been trying to raise funds to make the journey for a couple months so I can do all the interviews, but raising money has been a major problem for myself and this project. People don’t seem to realize how important it’s historical value to the arts and to creative people in general is. I’m having a heck of a time dealing with grant organizations, as even though most of them are art granters, they don’t seem to see the value either. But my friends who know art, and those that are in the film definitely see the value. I only wish they had the funds to help in getting the film made. But so many of them may have big spaces, but that’s because they’ve been in NYC since the 60’s when things were cheap, and they are kind of still living on that.

    So that’s what I’m here to hope for. An extended trip to NYC is really all I am asking for. Granted it would be awesome to be able to live there, but I know that if I can just get the extended trip. That the living there would come not too far off afterward.

    Thank you Tim, Ben, and Reid, for this opportunity. Great things are going to come from this particular blog entry no matter whom gets your undivided attention.

    Cheers to you and yours.


    here’s the project I’ve been talking about….

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

    I want to identify the leaders in the healthcare IT space. (Epic, Greenway Medical, Allscripts to name a few)

    I plan to update my cv and resume and apply to internships with all of them. With any luck the company which is hardest at work developing new consumer focused electronic health record system applications, will pick me up. (BS economics, MS Pharmacoeconomics near completion)

    In 30 years I envision healthcare technology which realizes some of the fantasy seen on star trek and I’d like to be a part of that effort.

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

    An internship may come without pay, or with too little pay to take care of my family. Not to mention i may need to relocate… Which may be difficult considering my wife is in vet school and we have small children. The position would likely require a bit of travel. It may be difficult balancing my family life with my work life which may add challenges to my marriage.

    I may be targeting the wrong companies for my long term goal. However, electronic health records are surely the foundation of future health technology applications, so I feel I can’t lose.

    I feel naive sometimes thinking I may be able to assist in solving some of our nations health problems. This may be an unjustified emotion though. The political climate has incentivized this type of effort through recent ‘meaningful use’ legislation.

    It seems it’d make more financial sense to toss my resume to all relevant employers and accept whatever seems to work. I seem to be excited about health care and technology though, and at this point I feel it’s either now or never.

    Thanks for reading. Now please help me mange this risk with a premium LinkedIn membership! Your time would be even better!

  86. Hi Reid,

    My name is Dwight Dillon Seminario. 7 Months ago, I decided to leave my life in California, where I had recently lost my job, and move to Peru where I have some family and start all over. I’m a musician with lots of experience playing and teaching and also a certified master hypnotherapist. My idea was to go to Peru, make connections and teach at the conservatory as well as start a new hypnotheraphy practice. I bought a one way ticket and now am working part time at the National Conservatory in the afternoon, and have a couple hypnotheraphy clients in the mornings.

    My most recent project within the next 30-60 days, is starting a company the specializes in video games for the iPhone. With a friend, we already have the design for our first game.

    The risk involved is spending our own money as well as raising money to hire programmers to write our game for us. Also the time spent learning how to operate and market the App store. The money I’m making for the steady check as a professor pays the bills, but that’s it. The hypnotheraphy practice is growing slowly. The real big one, is this video game. It’s going to cost us more money than we have together, and the rewards might not come for a while, but when they do, they’ll be through the roof.

  87. I am a 56 year old family physician that has transitioned my career over the past 26 years from that of a full time medical practitioner to a full time physician executive. I work as the Chief Medical Officer of our local hospital where I began practicing 26 years ago, fresh from my family medicine residency. Although very successful in this role, I have for years yearned to create a new business or become involved with an enterprise that would offer new challenges and opportunities for learning and growth. I believe that I have truly allowed my risk aversion to stop me from actively seeking such new opportunities.

    I have made some half-hearted attempts to interview for a new position and I am currently in the early stages of seeking a CMO job at a new hospital, but I fear that the closer this new job becomes a reality, the more likely it is that I will sabotage my own efforts. And what I would really rather do is take the skills I have developed in this highly regulated, low margin yet stable industry, including project management, team building and communication skills, and apply them to an unregulated, high growth industry. I could really use some coaching and advice to help free me from my self-limiting beliefs and move into this new position or to seek work in another industry.

    My primary fears center around the erosion of my ability to pay for college expenses for my youngest two children and the risk that I will not have sufficient funds to ensure at least a modest retirement for my wife and me.

  88. Wow. I’ve read >80% of posts on this blog. I don’t recall any of them being as provocative as this one (as evidenced by the 160+ comments already made). Tim, your ability to connect with people (guest-bloggers and readers alike) is uncanny, and your content is seemingly timeless. Keep it rolling. Thank you!

  89. My name’s Jonathan, I’m 27 years old, and I’m starting a health supplement company called Health Kismet.

    I make a greens powder called Incredible Greens.

    My big challenge: raising money for the next step in my company’s progression.

    The release of Incredible Greens has gone well, sales have steadily increased, and most of the vital signs have been improving.

    However, I’m reaching a point where Health Kismet either has to hydroplane or get an infusion of cash in order to grow. Developing a new supplement isn’t free, and I’m using my own personal savings….which are running out.

    So I need to put some time into growing my network of contacts that can eventually put me in touch with people who are willing to invest in a health supplement company, or people who would be willing to work with me on putting together a good pitch on Kickstarter.

    I need to start now because at the moment I DON’T need the money, and I want to ease my way into making the right introductions.

    This is particularly important because I don’t want or need a lot, and it’s more important to have it on the right terms than getting some arbitrary sum.

    I’ve spent much of the last 6 months refining my business systems to the point where I’ve whittled down my day-to-day activities into a productive routine and have automated most of the unnecessary.

    So I’m ready to begin sticking my nose into some fundraising, and am hoping that by being proactive I can do it on my own terms.

  90. Great article! Even if you are aware of our mental biases, they can play tricks on you. Nobel prize winner Kahneman admits this in his most recent book as well and he looked into human psychology and economics all his life.

    I urge you to print out the list of mental biased on Wikipedia (four pages) and stick them to your fridge.

    Now my actionable insights:

    I have a great job in the market research industry. High-learning opportunities, expanding company, a team full of smart people and you can have a beer with them.

    Why do I think I should take more risk?

    There’s little opportunity to “hit the jackpot” and I don’t like office (i.e. not being my own boss). I’m lucky because my quant skills are easily marketable.

    Thus, I pursue two options:

    1. Push for a 4-day work week (sorry for not quite following your advise here) but keeping the same salary.

    2. If that doesn’t work out, go freelance.

    Will happen before end of July 2012.

    Thanks for the push,


    P.s. Unrelated comment: allow me to say thanks, Tim, for your constant inspiration. I wrote this on my journey to a micro-vacation: Saturday highest summit of central Italy, Sunday beach.

  91. Dear Sir,

    Really inspired from this post….after understanding the basic relationship between risk and opportunity… i have my mind to join actuary course.

    I always fear that if i fail in that what will happen to my career….for becoming more resilient and successive manager ….we have to certain bold steps where other people hesitates and i certainly manage this situation now….thanks once again……i want to become very successful Actuary and please help me in that….thanks once agian

  92. Wow, look at all these comments! Looks like everyone wants a copy of that book! Count me in.

    Couldn’t agree more that the risk not taken is more dangerous than the one you avoid. In my 40s, I’ve had a reasonably successful career, doing all the right things – going to the right schools, studying the right things, taking the right jobs, making the right investments. That won’t work in today’s business world, or today’s economy. Looking at my gutted retirement fund, with no one knows how much more pain to come, I’ve realized I can only count on myself and my network of friends, family, and business associates to survive in this world. Depending on a single company, a single skill, a single career, is a recipe for disaster.

    I’m lucky, in a way, to be recently laid off. Now I’m taking my big chance and starting my own business as a product management consultant for consumer internet / software businesses. At the same time I’m taking advantage of the freedom to start building my own passive income systems to eventually build financial freedom for me and mine.

    It will be a challenge, but I’m looking forward to the freedom, the learning, and the chance to push aside my fears and create the career I love and an eventual life of financial freedom, doing what do only because I want to do it.

    Good luck to us all!

  93. If I may, I would propose a challenge to your post. You write about risk as though it is a choice that one must make in an instant – that the beast will leap out of the bushes and kill you if you don’t act now. You also seem to describe risks as having to be something huge and life-changing, without leaving much room for possible risks that are subtle. And that this mentality is the only way to take the risk you need to advance your career. (I may have misread you, but this seems to be the goal you are presenting.)

    (I would ask one question just for thought, if an entire generation adopted this way of life, would we not have a lack of stability in family, home, financial preparation for the future, and communities at large?)

    But I think that we can take risks in our careers without that split-second decision, or without it having to be a huge life overhaul.

    I am in the early years of an established career. (Stable, past entry-level, and qualifying for jobs that require 5-7 years of experience.) This is a great place to be, no doubt! Except that I’m not really happy with where I am. And I’m one of those people who never really knew what I wanted to do with my life. (I always thought I’d get married young, have a lot of babies, and be the happiest Suzie Homemaker. I’d spend my adult life cleaning, making jam, hosting all sorts of dinner parties, and raising the best kiddos in town, and lovingly supporting my bacon-home-bringing husband. But at 32 and single-as-they-come, with a good career foundation, I’ve begun searching for what I might do with the REST of my life!)

    So I have begun in-depth study of myself, my experiences, my gifts, my skills, my education (not just college, but all the things I’ve learned through simply learning and living!). My latest reads have been Marcus Buckingham’s books (“Stand Out” and “Strength Finders 2.0”), as well as “What Color Is Your Parachute” and “Do What You Are”. I’ve begun to meet with a career counselor. I’m taking inventory and studying for the future. I’m considering a few of the entrepreneurial ventures I’ve dabbled in, and making intentional plans with my time, energy, and resources. I still don’t have an ultimate plan or goal, but I’m forming it and will probably be forming it for a while (if not decades!).

    My point is this: “Risk”, defined as a split-second-leap-of-faith-decision doesn’t make sense for me. I wouldn’t even know where to leap to. I also don’t feel that I need to just drop everything, get in my car, and go start over somewhere. However, with study, personal growth, planning, and a lot of prayer, I can take large “Risk”, defined as a move to something that may be markedly less safe than staying where I am. A new career path may not have the same salary, comfortability, prestige, or status as the one I have now. And it may take years to develop respect in a new path. So while your article seems to lean more on the former definition of risk, I believe that it’s equally fair to give attention to the latter. Your life doesn’t have to turn upside down for you to take risks. And risks don’t have to be extreme to still be risks.

    1. Hi Rose. I see that you are studious career woman which might be one of the reasons for your confusion. It can take a long time to make a decision. There are research to be done, advice to be sough after, analysis to be done and so on. You’ve done all you can and now you make a decision(choice, go-no-go). The actual decision to take risk in of itself is usually very short, usually lasting less than 1 minute.(but can be much shorter) Once to made a decision, it’s time to implement what you need to do and your mind moves on. So the actually decision is a “split-second”, the preparation to make the decision can be very long.

      I am very happy you are in a established, stable, and accomplished career. (I mean wow.) You have a valid point of not having to take extreme risk in your career(or life) to call it a risk. One I would like to point out, that taking small risks is some times now possible. Others who misjudged their career stability and lost their job will have to make high risk decisions. There are also instances when small incremental risk taking is not possible. Personally, I find that risk taking actual takes practice. Life throws things your way(huge, significant and very unpleasant) ,And without practice one can panic, make less optimal choices. that’s my thoughts. hope it helped. Thank you for reading.

  94. I couldn’t have read this article at a more perfect time. I’ve always been drawn to taking risks, but lately that has not been the case. I studied Business & Chinese at Kalamazoo College in Michigan. My junior year I decided to study abroad in Beijing, China. It was such a wonderful experience that I decided to head back after graduation for an additional six months. When I returned this past January, I did some traveling around the US and ultimately decided that I wanted to stay in the US for the beginning of my post college career. I was very low on cash and decided to stay in my hometown of Detroit, MI. I got a part time job as a waitress and began working for free as an intern at a financial media startup. Days kept passing by and I never felt quite content. I think it has something to do with the general attitudes of people in Detroit. Everyone here, even the young college grads, is searching for stability, rather than excitement. That just isn’t me.

    So I began searching for other options in different states. I first thought about Raleigh, NC because I figured if I’m going to be a waitress who works for free at a startup, I might as well do that somewhere with nice weather all year round. Weeks passed, hundreds of hopeful emails were sent…and now (somehow) next Monday I’m moving out to San Diego, CA. I’m leaving with not nearly enough money, no job yet, no housing plans yet, a few friends there, and just a really big dream. Every time I start to worry about the uncertainty, I remember a couple different lines from 4 hr work week I have taped to my desk “The most important actions are never comfortable.” & “Failure is not an option.” I don’t know what’s going to happen, but I do recognize this nervous feeling in the center of my gut: excitement!

  95. To Ben, Reid, Tim, and all the Friends who have chimed in, my name is Hsu (Shu), aka Fatbuddha.

    Having spent the last decade of my life in and out of certainty, I’m no stranger to taking risks with my life.  Growing up in a somewhat typical first-generation Taiwanese-American family, I was the odd one in that I constantly had non-typical ideas.  

    My family was consisted of teachers, engineers, and farmers.  I joined the Peace Corps in Uzbekistan, foregoing my studies to become a doctor.

    My high school and college buddies all became professors and doctors, got married to people from their academic circles and churches.  I moved to China to find my career and married a wonderful Chinese woman, my wife JJ.

    I’ve worked in 10 different jobs since college, taking something away from each that I wouldn’t trade for the world.

    Looking back, I felt like I spent that last decade fighting against the cultural inertia of my culture in order to reach a place where I can positively evaluate the opportunities before me; I am finally not fearful of my potential to be successful.

    Last winter, I started working at Gaopeng, the heterogenous China offspring of Groupon and Tencent.  It was the startup of a lifetime, with so much hype, cash, and momentum to change the course of O2O business in China.  3600 employees and 200 expats later, the dust has settled, the money’s gone, and I’m one of the handful of expats who are still at the company, whose management is to be handed over to another group-buying company under Tencent.

    It was the most awesomest experience of my life.  And I couldn’t have had that experience had I not decided to leave my previous job.

    Which is funny thinking back, because it was right after I read Tim’s book, that I decided to outsource my job to a virtual assistant in Utah, successfully negotiated with my boss to work at home, so that I had more time to spend playing guitar, meeting new friends, and finding new opportunities.

    Tim, thank you.

    Now, it’s time for me to take the next plunge.  The experience at Groupon China has convinced me to pursue my own startup instead of just being an employee at one.  My goal is to develop multiple income streams and live life doing the things I enjoy.  I am now organizing web startup seminars, singles parties for our single friends, and life enrichment gatherings for the busy Beijing urbanite.  I am also writing an e-book on living a “No Bad China Days” life as an expat.

    Most of all though, I want to develop a mobile/web application that helps us map out our personal contacts via the cloud.  Which is essentially LinkedIn on crack.

    To all the friends who have read my post thus far, this is my goal for the next 30 to 60 days.  To find a partner who shares my vision and to build a small team to prove this concept.  

    If any of you are in Beijing, I would love to meet and chat about anything!

    Thanks again guys, happy risk-taking!

    Fatbuddha in Beijing

  96. Hi,

    My name is Damien, I’m 22 and have been truck driving for 3 years to save money for helicopter flying lessons.

    I have a lot of spare time in my job and want to either write an e-book or sell products online to create a passive income of $5000 per month to fund my dream of becoming a chopper pilot. Trading my time for money feels like banging my head against a brick wall and at my age I am already sick of it.

    My dream is to not only become a pilot, but own my own aircraft with a large enough passive income to fly around Australia and visit friends and family and live life.

    The risk involved financially is fairly minimal (I think), but quitting my job to create online businesses is something I know little about but like the idea of. Also, announcing to friends, family and peers my intentions to ‘not work hard’ could be an insult to their ideas of making money/careers/jobs/financial security etc. This risk of being ‘a failure’ in their eyes is daunting. But it is my dream nonetheless.