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 can attest to working overseas and maintaining a present via virtual office. I do it, my clients do it, and it has sprouted a freedom that I never knew before. I can be in two places at once and run free without anybody knowing I’m “gone” as long as my virtual team and I meet deadlines and fulfill contracts.

  2. In the past I have been a person who “played safe” most of the time. The last decade I learned, that there is nothing stable and now I really enjoy it. Instability forced me to work on my strengths, my portfolio and most of all: made me more willing to take risks and try out new things. I have not arrived where I want to be but the journey so far was full of great adventures and successes

  3. Great Post, thank you

    Even though I’d be working just the same, it’d be the first time somebody worked remotely from outside the country. It’s a totally novel take on where and how work can get done. It might not go over well. They might decide to cut me loose and I’d have to start all over.

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

  4. Hey there just wanted to give you a brief heads up and

    let you know a few of the pictures aren’t loading properly. I’m not sure why but

    I think its a linking issue. I’ve tried it in two different web browsers and both show the same outcome.

  5. The problem with western style of motivation and positive thinking is that it tends to teach people to follow fixed concepts. It is never a wise decision to categorize or crystallize in any fixed classical form, in whatever you do. Do not permit yourself to be locked down by any fixated styles, patterns or fixed mental algorithms. Whether you are just an employee working for a boss or a self employed, or a business owner, it all depends on the timing and the situation plus surrounding factors. Ever heard of right place at the right time? That is destiny and the Way. You just know it when it is the right time to do something, that gut feeling. Just be ready to strike when the moment for you comes. Be fluid like water and you will find your Way.

  6. In my previous comment has come out with a different direction, this time is ready, thank you for this great content. “The art of hitting, implies having failed before”.

  7. Risk: Quitting my job warehouse job that was eating up all of my time and sucking the life out of me! I worked in quality control. It was an ok job, but there was no room for me to advance and there probably wouldn’t be many raises. I was only working there because I felt “safe”. To top it off my boss was a clueless, inappropriate jerk. She was verbally abusive half of the time. I had only been there a year, which was the longest any of the new employees stayed. One girl left after 3 days, and my best friend left after a week! Over the holidays I picked up the 4HWW out of curiosity and to give me some clarity. After reading the elimination and fear setting chapter, I sat and pictured the worst case scenario. The only thing that came up was I wouldn’t have my own income. I could live with that so I quit! Now I’m coming up with ideas for an online clothing store with small collections. So far it doesn’t look too difficult! Just getting the specifics, costs, and trying not to let my doubts get the best of me! If everything goes good I’ll be doing something I love to do and have the freedom to do it!

  8. Hey everyone,

    I posted a while back about how 4HWW changed my perspective on life. I was not sure the direction my life would take but I quit my job and moved to California. I am now working at a job at an order fulfillment company called FulEx that I absolutely LOVE because it helps people who want to have a 4 hour work week! Most of clients have read the book or are on kick starter. If you need any help feel free to reach out to me via LinkedIn. Gena Taylor

  9. I would like to say that after reading your book the 4 hour work week in one sitting that I was motivated and compelled to do the most unthinkable thing…I walked away from my job that had no longer fulfilled me feeling my skills were not being used to there full potential.

    This article has got me hooked on taking risks..despite according to a personality test I recently did revealed that as a risk taker it sits at 63.38% and should not be done…WOW!!! I am now taking the risk , what is the worse thing that could happen to me …absolutely nothing.

    Valarie Timlin

  10. hi, I am kuzhali, I completed My MBA FROM AU with major finance and minor marketing in 2011 its been almost 24 months that i am unemployed, i feel like i have lost everything its almost impossible to convince the HR why there is a gap of 2years what to do plz help nd give some examples?

  11. I have read the blog and I am very impressed. I am a fresh graduate and got placed in two companies. Qualcomm, associate engineer with a nice pay and mu sigma where I will learn a lot related to analytics. Can you suggest me where I should proceed as picking mu sigma is a risky affair?

    Thank you

    Anoop yelisetty

  12. I have been running a granite worktop business for nearly 10 years with my husband. We separated a year and a half ago because we have extremely different business ideas. He wants to stay in this one so in order to move in the direction I want I have to leave. My vision is to run a business from my ipad so that I can travel while running it. I recently read about a lady who set up a business and focused on “getting thank you notes” and her business did 300% better than other businesses in the same industry. I believe it is better to focus on something that benefits everyone involved rather than just making money. Any ideas?

  13. one of the most effective How to Take Intelligent Career Risk (and Win Mentoring from Reid Hoffman, Chairman of LinkedIn) I stumbled upon so far

  14. Thanks for your posting. My spouse and i have often seen that almost all people are needing to lose weight simply because they wish to appear slim as well as attractive. Even so, they do not always realize that there are more benefits to losing weight also. Doctors claim that obese people come across a variety of conditions that can be instantly attributed to their own excess weight. The good thing is that people who sadly are overweight and suffering from numerous diseases can reduce the severity of their illnesses simply by losing weight. It’s possible to see a continuous but noticeable improvement with health when even a minor amount of weight-loss is achieved.

  15. This was a great article. I never understood my fear of risk until now. A business idea that I would like to embark on is opening a juicery in low income areas around Buffalo, NY. Especially around the waterfront. I would also want the consumer to be able to pay with food stamps. I have family in the area and it’s hard to find one healthy option. Thank you again for your blog.

    Julie J. Cornwell

  16. This definitely taught me a lot about how the human brain works and how this is related to career success or failure. This is something that definitely makes me think differently about these things.

  17. Those affected by long-term unemployment need to realize few very important facts. We are living in a new economy driven by innovation and transformation with an over abundance of resources available to create new business models and market situations. Most industries are adapting to new to new market expectations, facing a variety of indecision gaps in front of incongruities.

    As an example health care has issues regarding organic revenue growth, the food industry is adjusting to the Food Safety Act of 2013, the pharmaceutical industry is adjusting to the new product development model, and new energy technologies are transforming power management. In other words there are a number of strategic concerns requiring high level business – technology expertise. These market situations are transforming into high value career development opportunities with a prerequisite for entry being deep level expertise in a combination of technology-business in just about every market sector.

    What is nice is there is no rulebook for entry just some simple process experience blended with technology and marketing backgrounds.

    The key is looking at industries instead of companies, finding the market gaps. You might be very technical in nature might not have the ability however most likely you know someone out of work who can. Contact that individual and decide to work together.

    During my mid stage career I decided to think long-term and pursue health care and advance technology. Along with my partner we created a new health care model, introducing it to the provider market and within four months had our first project, within 2.5 years new fulltime consulting jobs with benefits. The same think can happen to each of you reading this perspective. Take advantage of your age, experience, and functional and industry insight……and create your next career position.

  18. i am from india and an undergraduate mechanical engineer,just passed out in 2014.

    the college where i studied was not that reputed and we had no campus interview literally nothing for mechanicals ……but i struggled for 5months and found an job in an aerospace industry as quality engineer but i left that company in 3months and now i am unemployed …i left the job because i felt wrong about getting bribe and assuring the fake quality of products and many more unwanted and repugnant reasons ,some personal like guilt some relational some like non coordination last i left it …but i feel i under estimated the oppurtunity which was given to me but have an happiness that i took risk for good cause ..but money is money it doesnt know good or bad …..after that i tried all things but i every time lacked in the reference for an job in india and realised that lack of knowledge about oppurtunities caused me this situation and then nothing just patiently searching an job …….i lossing my confidence,enthusiasm,anticipation,prespiration etc… also underestimated or not even tried for some oppurtunities which came to me …confused and still cant able to untie the knot ……………..i request some knowledged person to guide me bcoz no one in my family,relation,friends, studied engineering …but now for the first time leaving everything on fate and searching for some help from some where ….thanks for reading if some one did so….and sorry for wasting your time with sharing my words ,which u can see on any sites like this because i found 7/10 of indians do the same expecting miracle without effort but i did the same bcoz efforts at wrong place or in wrong way is a waste….ok bye have a confident move in the life

  19. Hi ,

    I think i will get my answer from you .

    Well , i am working in asset management company for last 7 years. My profile is to meet bankers / distributors and convince them to sell my company mutual funds . In my current profile i think the growth is not fast and rewarding as other jobs because of less demand in my current work industry . The supply of asset managegement sales profile are even higher . So less demand and more supply means less growth . On the other hand i want to change to wealth management profile for which the job is very much awailable within the organisation . But i feel like i am not having the kind of client base or may be i can do it or not . The wealth manager profile is in high demand and best in perks . I feel like it will be risky for me to change to this profile as i am married and have kids too . If i switch to the new profile i will learn a pertikar skill of generating good revenues for my organisation by convincing ultra high net worth individual clients for investments . What do i do . Should i take this risk .