“The courage to be vulnerable is not about winning or losing, it’s about the courage to show up when you can’t predict or control the outcome.” — Brene Brown in Dare to Lead
Human beings are creatures of control.
We crave certainty. Where certainty doesn’t exist, we’ll accept probability. As a rule, we like to know the outcome before we start.
It’s why people tend to stay in jobs that make them unhappy for years and even decades. They make a calculated trade of happiness and self-actualization in exchange for certainty.
Golden handcuffs.
Just tell me my job is secure and my wages are guaranteed, the thinking goes. Give me good benefits, a strong pension at 65, and I’ll serve you for life.
That’s how highly we value certainty and stability.
The safe life.
Sure, we all entertain dreams from time to time. Dreams of doing the extraordinary. Of making a bigger impact. Of making greater contributions in the lives of others. Of attempting the bold and ostentatious, whatever that looks like in our world.
We dream of showing up in a big way. But as long as it remains a dream, the outcome is certain — zero chance.
If All We Had to Do Was Dream
I mean, the dreaming part is fun. Put a guaranteed road map in front of me, and my willingness to show up for the extraordinary shoots way, way up.
- Tell me that if I launch a small business, it’ll be instantly successful and cash flow positively within its first year.
- Tell me that if I buy an investment property, I’ll be able to find fantastic tenants and the property will appreciate steadily over time.
- Tell me that if I launch an NGO, it’ll seize the imagination of thousands and make life-changing impact in a developing country.
- Tell me that if I become a realtor I’ll be able to sell multiple listings per month from the outset.
- Tell me that if I start working on a Youtube channel today, I’ll have 1M subscribers in five years.
- Tell me that if I study for the LSAT, I’ll pass the exam and be accepted into law school.
- Tell me that if I do the research and work to write a book, it’ll become a bestseller.
Of course, none of us have those sorts of guarantees. Sure, there are principles of hard work and investment that we can rely on to a certain extent. But no guarantees.
And so we tend to be a little cagey about showing up for risky ventures. About sacrificing to make big changes. About actually showing up when outcomes are uncertain.
So we hedge our bets.
The Many Fears of Failure
The fear of failure looms large. Unpack the fear of failure, and we find other fears.
- Fears of rejection.
- Fears of appearing foolish or naive in the eyes of others.
- Fears of forever losing the time, energy, and capital required.
- Fears of social judgment — “Who do you think you are, anyway?”
- Fears of what we would have to say to ourselves if we were forced to admit defeat.
YouTube: A Case Study
I remember when our 14-year-old was 12. For a while, he was intensely interested in editing videos. He was dramatic, creative, and enjoyed performing.
He launched a YouTube channel at the time and dabbled for a while. But I saw his concern about going all in — say, committing to weekly publishing.
The fear of low views and poor response was real. What would it say about him if he went to all this work and there was little to no positive response? Could that result be even worse than never trying anything at all?
Those questions don’t go away in adulthood. They only get louder.
Fear is Something to be Dealt With
One quote that made a big impression on me last year was this one from Elizabeth Gilbert, who writes about risk-taking in her book, Creative Living Beyond Fear:
“Fear is always triggered by creativity, because creativity asks you to enter into realms of uncertain outcome.
This is nothing to be ashamed of. It is, however, something to be dealt with.”
In 2019 I applied for a job that I really had no business getting. I lacked the appropriate experience, and the responsibilities would have been somewhat over my head, at least at the outset. But I knew the interview would be a good step, a good stretch for me. And sitting around the table with five people, thinking on my feet, analyzing my own strengths, weaknesses, ambitions, and vision was a valuable process.
I showed up. And I’m proud of that, because that’s the person that I want to be.
But I’m not finished. There’s still a ton of sacred safety in my life — spaces where I have yet to step out, take more risks, and embrace more uncertainty.
I have more showing up to do.
What it Looks Like to Show Up When Outcomes Are Uncertain
When I think about what showing up in uncertainty can look like, I think of some great people:
- my brother Peter and his wife Shannon, now in the process of acquiring their fourth business by the age of 35,
- my cousin-in-law, PJ, whose online startup continues to win big contracts,
- my friend Karalee, who recently moved away from a secure job to launch a new business in a completely different field,
- Trevor, a teacher, who designed and patented a new sport and recently wrote a novel on the side,
- Chris, who is starting a new career in real estate at the age of 40, and
- Jen Rao, who left a well-paying job and sold her home to live a life of mobility and remote work.
I could share more examples. But to me, this is what it can look like to step out and show up in big ways, even when outcomes are completely uncertain.
I salute this group.
What Might Have Been
It’s been said that the most common regrets of the dying are not the things they did but the things they didn’t do. The things they didn’t have the courage to try.
What might have been.
Let us not be those people. Let us not live our lives wondering what might have happened. Let’s go for it, even when the outcome is uncertain.
It doesn’t require quitting your job. But it does require facing your fears.
It requires showing up — even without a guarantee of success.
“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again … who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly.“
– Theodore Roosevelt
Tim Cavey 