The Biggest Regret from my Twenties

“Don’t ever let anyone ever say to you, ‘You shouldn’t regret anything.’ Don’t do that, don’t! You regret what you fucking want! And use that, use that, use that regret for anything, any way you want.” -Earl in Magnolia 

I have climbed highest mountains
I have run through the fields
Only to be with you
Only to be with you
I have run I have crawled
I have scaled these city walls
These city walls
Only to be with you
But I still haven’t found what I’m looking for
U2, “I Still Haven’t found What I’m Looking For” 


Fresh after graduating from undergrad, I remember boasting to a female friend of mine that the twenties were about seeing the world, trying a bunch of different internships, going to grad school, making a bunch of mistakes, and racking up a credit card debt. I don’t think she was very impressed.

More recently, a friend of mine and former college roommate told me, with some degree of admiration, that I had lived exactly as I said I would in my twenties. There’s probably some truth in that. I was a total thrill seeker. In the last decade, I have visited three other continents. I lived in Northern Ireland for a year, not to mention as many as five American cities. I “taught for America.” I’ve gone through two rounds of grad school. I’ve said goodbye to a few relationships with women. I moved almost every year, which of course meant constantly making new starts, trying to build new relationships. It wasn’t all bad, and I definitely developed a few skills and made some memories along the way. Hopefully, someday I won’t abandon a family in my forties because I think backpacking Europe will lead to my salvation. Been there, done that, and mostly it was…lonely. Thrills mostly fail to deliver; they don’t fill the void inside me that longs for meaning and to be known and understood.

Burying my brother had a way of changing my perspective. The trouble is: the life I’ve been living for so long just isn’t sexy anymore. I turned thirty in June, and the lead-up and aftermath has definitely seemed like my own quarter life crises. It was hard, painful, and probably very necessary. What am I living for? Does anyone really know me? Why are my commitments still so ankle-deep? Youth is worth grieving, even as age, growth, and maturity are worth celebrating. I don’t think we have to choose between the two.

I can definitely go too far in the direction of harsh, self-scolding, but I can also allow these realities to change me. Several years ago, a man told me to make sure I was running toward something, not away from it. For a positive example, take Lebron James going back to Cleveland. I nodded my head to that man, then kept running away from things.

I don’t know exactly what this looks like for me and obviously it’s not all in my control, but I want to quit running. I want to build something: a home, a commitment to a place, a career, and if I’m lucky, a relationship with a woman. So I guess that’s my vision for the thirties: build something. Here I come…

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