The Biggest Risk

I should be writing business school apps, I really should. Unfortunately, my mind has been as prone to wandering as it has been to focus lately. As a result, I find myself writing again, but nothing even remotely practical.

I’ve been doing a lot of thinking lately about life, about what it means to be successful, and ultimately what makes us happy. If you’ve been around me long enough, you’ve probably heard me ramble about eternal recurrence-a theory of individual life postulated by Nietzsche. An unattainable ideal, eternal recurrence is the idea that we should be prepared to be reincarnated in perpetuity, but living the exact same life for all eternity. You’d relive every heart-warming success and agonizing defeat on repeat for infinity.

I asked myself: what would make me comfortable with that scenario? What makes people successful on their own terms, regardless of background or creed? In the simplest terms, I guess this question could be asked another way: what do people regret at the end of their life?

As I reflected, I came to the conclusion that the things we live to regret are rarely the things that we do, but are almost always the things we don’t. The one that got away. Man I wish I’d told her how I’d felt when I had the chance. Or just kissed her, been a man. The career that we never tried. I always knew I’d make a great lawyer, always. Monuments they skipped, countries they never visited, and events they’d found some lame excuse to miss. Even when we take a big risk, we are rarely more disappointed than we would have been with ourselves for not trying. At the very least, pushing ourselves outside of our comfort zone makes us feel alive, even if it’s not for us. No one has ever been exhilarated from their living room couch.

Sure, we can live to regret the way we treated people, the marriages that didn’t work, and the opportunities we tried to take hold of, but squandered. I’d just rather live with that regret ninety nine times out of a hundred over seeing a coward looking back at me in the mirror.

Now, I’m not saying that I’m going to go base jumping or some equally foolhardy attempt to get myself killed; I’m still a risk averse person deep down and venturing outside my comfort zone is a skill that I’m learning in a lot of capacities despite what my forays into sky diving and bungee jumping might lead you to believe. All I’m saying is that I’ve taken the leap a few times over the past few years, gambling on myself, and it’s been an incredible experience. I’ve taken risks in love, my friendships, and my professional career that have required a bravado and honesty, both to myself and others, that I was previously unable to summon from within.

Taking a broader view, it’s clear that those deserving of our respect, from professional athletes to entrepreneurs to presidents, have taken calculated risks in the face of others calling them crazy or, worse, hopeless dreamers. No one has ever changed anything by playing it safe; the trick is knowing when to take a calculated risk and when to give up. Sure, it means more failure, but what does the inability to take these risks and gamble on ourselves say about who we are? The most successful entrepreneurs, for instance, are prepared to fail 10 or 11 times before hitting it big. A venture capital firm only needs to hit a few home runs in its entire portfolio to be a tremendous success, meaning that it must become extremely comfortable with repeated failure.

Examining myself, I know that I don’t need to found the next Google, but my own personal hell would be a world where I’ve stopped growing as a person and settled into a comfortable bureaucratic role somewhere, rubber stamping forms for eternity. Where my journey will lead me, I’m not sure, but I do know that I need to continue to push myself towards taking the kinds of risks that will ultimately enrich my life, scary or not.

Call me an unrepentant existentialist (and I am), but I want to be able to lie on my deathbed comfortable with the choices that I’ve made, the man I’ve become, and the lives that I’ve touched. I want to be prepared to relive this life on repeat, as absurd as that may sound. I could throw a million clichés out there about what that means: fortune favors the bold. You can never burn a bridge without looking back. Etc, etc, etc. In the end, I think we just need to admit ourselves that sometimes the biggest risk is not taking one at all.