October 10

A Tolerance for Uncertainty is the Price of Admission for an Extraordinary Life

Whenever you set out to do what’s never been done before in the way you want to do it, you risk losing all sorts of things— time that could have been spent doing something else, money that could have been saved, prestige, status, income or the perception of security- Jonathan Fields

For most people,  uncertainty fills them with fear, panic, and anxiety. It causes them to dream up catastrophic worst-case scenarios, most of which never come true. It keeps them playing small instead of big, and in the stands instead of the arena. But in any life in which you don’t just choose from the options in front of you, uncertainty is inevitable. Extraordinary achievements are rarely the result of a predictable, safe, and linear trajectory.

Actors go to Hollywood, founders go to San Francisco, and musicians go to Nashville even though the odds are stacked against them and their future is uncertain. They give up an ordinary life for the potential of an extraordinary one.

A tolerance for uncertainty is the price of admission for an extraordinary life. 

Fortunately, our tolerance for uncertainty isn’t fixed. It’s something we can develop and increase with practice. As we develop our tolerance for uncertainty, we’re able to navigate the geography of a creative life more with poise and grace.


If you want to become extraordinary at anything, you will have periods of discomfort:

  • If you’re an artist or creator of any sort, you’ll have to tolerate the discomfort of creating work that’s not very good
  • If you’re running a business you’ll have to tolerate the discomfort of  financial uncertainty
  • If you do reach a point where your products, services or books reach millions of people you’ll have to tolerate the discomfort of 2-star reviews and of the fear that you’ll never be able to produce the same quality of work again

Discomfort is a non-negotiable part of any life where you attempt to be the architect of your reality.  We crave adventure, purpose, and meaning. Yet, We seek out safety, profit, and security.  To do anything extraordinary, you must accept the duality that nothing is guaranteed and anything is possible.  As Susan David says, “discomfort is the price of admission for a meaningful life.”

The Illusion of the Perfect Time

Most people go through life thinking that tomorrow they’re going to do something great. Tomorrow will be the day they wake up and discover what there were put on this earth to do. But then tomorrow comes-and goes. As does the next day. Before long, they realize that there aren’t any tomorrow’s left. – Nick Bilton

A few months ago, I was having dinner with a friend who said he didn’t understand how people left their secure jobs with steady paychecks to start companies. In response I said “you realize the only reason you have a job is that someone else had the balls to do that right?”  In his eyes there was some mythical date in the future when the conditions would be perfect, the time would be right, and he’d have all his ducks in a row.

There’s no guarantee that you’ll make it to tomorrow, next week, next month or next year.  My friend said, “why not wait until later in your life?” I reminded him about our mutual friend whose life was cut short by a tragic drowning incident just a few weeks earlier. It doesn’t matter when your brief moment of audacity takes place. It’s always going to be uncertain There will never be a time when you will be able to predict precisely how the future unfolds.

The Illusion of Security

The so-called recovery from the Great Recession has been among the most anemic recoveries in all American economic history, especially given how far the economy fell in 2008 and 2009.  – Robert Reich 

When I graduated from business school in April 2009, the economy was in a tailspin. People with decades of work experience were applying to jobs that paid less than 10 dollars an hour, and companies were receiving thousands of resumes for one job. I’d hear classmates talk about some time in the future when the economy would improve. But it was clear that many of the jobs that disappeared because of this recession were never going to come back. The economy hadn’t improved.  It had fundamentally changed. We had gone from being in a system that once rewarded people for fitting in to now being in one that rewarded people for standing out.

As somebody who had been fired from most of my jobs, I saw the idea of a secure job with a  steady paycheck as an illusion. I knew where that road ended for me, and gambling on the uncertainty of my entrepreneurial endeavors was far less risky.  If I got fired from yet another job, I’d have more bullet points on my resume. If I started something, I’d at least have a body of work. Building a body of work is a bit like taking out an insurance policy on your career.

As my friend Joseph says about secure jobs with steady paychecks “When you have a job you have one client. If that client fires you, you’re hosed.” When you have a business, you have more than one client. It might be more stressful and uncertain, but at least your risk is diversified.

Does that mean everyone should start a business? Absolutely not. But if all you’re doing is adding more bullet points to your resume, you’re playing Russian Roulette with your career.

For decades technology has made us more efficient by displacing labor.

  • ATM’s reduced the number bank-tellers
  • Airport Kiosks reduced the number of ticket agents
  • IPAD’s are reducing the number of servers at restaurants

Up until now, technology primarily replaced blue collar labor. But with the rise of automation and artificial intelligence, we’re about to experience displacement of white-collar labor.  Repetitive cognitive work like accounting, SEO, and more are all being gradually displaced. As presidential candidate, Andrew Yang says in his book The War on Normal People: 

Right now some of the smartest people in the country are trying to figure how to replace you with an overseas worker, a chapter version of you, or increasingly a widget, or software program or robot. There’s no malice in it. The market rewards business leaders for making things more efficient. Efficiency doesn’t love normal people. It loves getting things done in the most cost effective way possible

The Myth of Linearity

Until we reach adulthood, we experience life in a linear trajectory. We progress from grade to grade, one degree to another until we find ourselves in the real world.  Because we’re so conditioned to follow a linear path, we assume it’s the same in the real world: get a great job, climb the ladder, fall in love, get married, buy a house, and have kids. But very few people who reached the pinnacle of achievement seems to follow this path. People usually become CEO’s because they start their own companies, not because they gradually climbed the ladder. If you’re a middle manager at a large company with 5000 employees, the odds you’re going to be CEO are 1 in 5000. It doesn’t take a statistics degree to know those are piss poor odds.

In my conversation with Alex Banyan about how the world’s most successful people launched their careers, he said the following:

The first path is linear: go to school, get a job, pay your dues, climb the ladder, etc. The second path is exponential. You skip steps. You ignore convention and conformity. You defy the status quo.

If you plotted the both of these life paths on a graph, the linear path would initially appear to a better choice. It would appear safer, secure and more lucrative. The exponential path would initially seem risky and unprofitable. But if you look at both paths on the graph five or ten years in the future, the exponential path will shoot up, while the linear path eventually hits a plateau. Choosing the second path isn’t easy. It requires you to ignore your social programming and temporarily deal with doubt and disappointment from many of the people in your life.

Navigating Uncertainty

A lot of the power of rituals and routines comes from the simple fact that they are always there. They are grounding experiences to which you can always return.   – Jonathan Fields 


One of the main reasons I write 1000 words every morning is that it gives me what my friend Jonathan Fields refers to as a certainty anchor.

It helps me to navigate the inherent uncertainty of a creative career without feeling like  I’m going to lose my mind. By having an anchor, whether that’s a meditation practice, journaling practice, or exercise habit,  we add a little bit of certainty to a life that’s inherently uncertain.

Process Orientation

It might take a writer over a million words before he gets a book deal. It might take an actress more than 1000 auditions before she lands a starring role in a movie or TV show. There’s no such thing as an I’ve made it moment.  There are just the seeds you plant for the person eventually want to become.

Our outcomes are unpredictable, but our process doesn’t have to be. By adopting a process orientation, we’re able to develop a growth mindset, focus on progress instead of perfection, and make the uncertainty of a creative or entrepreneurial endeavor much more tolerable.

Emotional Agility and Resilience

When you face one rejection after another, or when something fails to meet your expectations you’re going to be disappointed. While our massive failures do often become gifts from the universe, it doesn’t change the fact that a situation sucks.   We put a lot of energy and effort into making ourselves feel better.  But what if that’s precisely what’s causing us to suffer?

According to psychologist Susan David “Trying to correct trolling thoughts and feelings leads to us obsess unproductively on them. Trying to smother them can lead to a range of ills from busywork to any number of self-soothing addictions. And trying to change them from negative to positive is an almost surefire way to feel worse.”

Every single time, I’ve surrendered and accepted the circumstances of my life rather than fight them, amazing things seem to happen. Loss creates openings in our lives. When we don’t fight those losses or fill that space with fear, panic, and resistance,  each loss has the potential to be replaced by a much greater gain.

Every time you get back up after you fall, you become more resilient. As I said in my last book “your shell hardens but your heart softens.” When that happens you become more powerful, more resilient, and your tolerance for uncertainty increases.

Don’t just Look at the Limitations. Consider the Possibilities

It’s possible you’ll fail, fall flat on your face, get rejected and get your ass handed to you. But it’s also possible you’ll achieve far beyond what you currently dream is possible, experience more joy than you never have before, and soar to unimaginable heights. Just because an outcome is uncertain, that doesn’t necessarily mean it’s going to be bad. This became clear to me in a conversation about making decisions with Michelle Florendo.

For decades we have been conditioned to believe the greatest lie we’ve ever been told and to choose from the options in front of us. We’re taught to follow safe, well-lit, predictable, linear paths. But the supposed safety, security, and certainty from doing so are illusions that keep us from daring greatly.

The magic in our lives takes place on the edges and outside of our comfort zones.  To do the greatest work of our lives, we have to use a compass instead of a map, follow paths that aren’t well lit and don’t come with any guarantees. “Uncertainty is a form of limitlessness,” says my friend Reema Zaman. It’s only by embracing uncertainty that we can discover the limitless potential and infinite set of possibilities in our lives.


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