What’s a Risk You Took That Wasn’t Worth It?
01.22.18

For the most part, I have been able to coast through my life avoiding the cost of taking substantial risks. This might sound unusual given the condition of my occupation as a business founder, but the reality is I was still in school when I started Man Repeller — living at home and off an allowance donated by my parents that never forced me to sacrifice anything to launch a company. Following graduation, the risks that I took for Man Repeller, already a profitable entity, were highly measured and contingent on the aforementioned profit. Hire only when you can comfortably afford it; grow it slowly and steadily; if it fails, quiet it down to pursue a “real job,” I would tell myself.

I have been, by all means, the dream client of a risk assessment manager, mitigating the presence of high stakes with financial cushions and calculated steps and with as much conviction as I have when I wear a dress over pants. But lately, I’ve been wondering if you can live a meaningful life sailing among the waters of low stakes (so much so, that I tweeted as much, and prolific Man Repeller contributor Meghan Nesmith volunteered to more formally cogitate on it). Are risks worth it even when they’re not — that is, when the intended outcome is never realized? How profound can an experience be if you never truly put your ass on the line?

This morning I asked my husband about the biggest risk he ever took. He said it was getting back together with me when he was 25; the pressure of becoming my boyfriend again after three years apart, and the implication that he would have to make some version of a commitment scared the hell out of him. But was it worth the reward? I will answer for him: Of course. Two years ago, he also quit a very comfortable job to start something new with, of course, no guarantee of success attached. He counts that as one of the most satisfying risks he has taken despite the ongoing incurrence of a pay cut. Not very helpful for the purpose of this story, but maybe that’s the point.

The human condition is such that no matter the outcome, we will convince ourselves that the decisions we make are the right ones. That we are exactly where we’re supposed to be. That even a risk that results in turmoil — mortgaging your home to start a business and failing; leaving your partner because something better might be out there only to find yourself unhappily single after a decade; turning your life upside down to move across the country and learning you hate where you have landed — is the most valuable of the lessons you learn. It’s the crux of what builds your character, makes your perspective more dynamic, and is the very essence of your upward maturity trajectory. And when you succeed following a great risk? Oh to be ballsy and right! The sense of achievement must be palpable. It must be why we bother with risk at all.

But the question remains, can you think of a risk you have taken that wasn’t worth the reward, or lack thereof? Frankly, I can’t, which is perhaps because I am so risk-averse. But I plan to change that — you just wait and see what I mean.

Collage by Emily Zirimis.

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