The Lives We Didn't Live
Sometimes it’s better to insulate ourselves from the world of infinite possibility.
I’m at the age when, all around me, friends are splitting off into two camps: planning weddings, baby showers, baptisms, adoption parties…or heli-skiing in Revelstoke, swimming with sharks, and ending up in accidental throuples.1
Humans are wired for connection. But our twenties are a hard time to make life commitments. They’re a hard time to do anything. We’re still working out who we are, what we’re into, and usually the only way to discover anything notable about ourselves is to make a series of temporarily disastrous mistakes. We lack perspective, we’re useless to workplaces everywhere, our blind enthusiasm is terrifying, and no one will show us how to send a fax or explain why a fax machine has persisted over two decades into the new millennium.
In my teens and early twenties, I lived by the Regret Minimization Framework. At every juncture, I chose the path that would close the least doors—using prestige as a proxy for opportunity:
Creative Writing or AP Computer Science?
Teach For America or investment banking in New York?
Room with friends in the Lower East Side or get my own flat in Midtown?
I ended up leaving my IB analyst program after six months, giving up my New York City studio, and trying on five different roles within five years out of school. I benchmarked on external validation because I hadn’t done the inner work of discerning what I valued, how I wanted to spend my hours, and who I wanted to be in the world. I was asking the wrong questions and defaulting to other people’s ideas of success. It wasn’t ‘How do I succeed?’ but ‘What is success [a good life] to me?’
Last year, my investment banking analyst class met for a mini-reunion in Austin, equidistant from New York and California. We studied each other with amused incomprehension: one of us stayed in banking, two graduated to private equity, another to corporate finance, and I moved into tech.
Some of us are homeowners, some are engaged (or married—congrats Dom!), some are living the Central Park financier lives we always dreamed of living, and some took several detours to figure out what we truly wanted. We’re scattered across the country now, and the divide between our lives continues to widen. But at some point, as wide-eyed twenty-two year-olds, we were all on the same path.
It’s like we sprouted from the same tree, but one blossomed into a hydrangea and another into a pinecone. Studying one another was the closest we had to peering down the paths we could have taken.
Life is a non-repeatable experiment with no control. We all get one shot. The hardest paths to look at are the experiences we didn’t have, the time we didn’t spend, the commitments we didn’t make, the people we didn’t love, the lives we didn’t live.
After Pete Davis’ Dedicated: The Case for Commitment in an Age of Infinite Browsing, I can’t help but wonder if the adventurousness of the latter is required to feel something, anything, in the absence of deep, meaningful commitments in our lives.