In the wilds of Reddit, I came across a hypothetical question: If you could go back to when you were 27, would you? They couldn’t have picked a more perfect age for this question — that was the year I moved from Chicago to San Francisco and my life really began.
I was living in the attic of a quaint Victorian in Glen Park, a neighborhood that hadn’t been discovered yet, and commuting down the coast to Half Moon Bay. Every day I zipped down iconic Highway 1, just a sheer cliff face separating my Acura from the Pacific Ocean, and had to pinch myself. I lived here, in this gorgeous place! That thought would run through my head on repeat: I live here now. I live HERE. It wasn’t a great job but I was so thrilled to have made it to the west coast it didn’t matter. For the first time since I left for college, I was home. Everything felt lighter and brighter.
If they had chosen an earlier age, my answer might be no even though college and beyond were tough years socially and emotionally for me. I just didn’t belong in the Midwest. While Today Me would know how to make those years happier or make different decisions that would change my trajectory, it would come at a cost. Looking back it’s remarkable how goal-oriented I was, how driven I was to excel in college and start my career. Who I am today no longer has the patience to grind out all-nighters or the enthusiasm for the entry level work needed to prove myself.
But 27? Hell, yes, I’d go back! It’s the perfect inflection point — I could do even better, without sacrificing what led up to it. The next decade would bring the social life I’d dreamed of, so I wouldn’t change a thing about that. Although it would be lovely to host all those dinner parties again, before so many friends moved away and started families. I’d still go to graduate school.
On the other hand, I could have done more in other areas of my life. If I had a do-over I would switch careers earlier, travel more (even if it was alone), and save harder for retirement. And certainly I would scoop up a house in the post-2008 crash! Instead I took a more laid-back approach to life, letting things unfold — not a mistake by any means, but also not seizing the advantages of youth. As cliché as it is, I don’t know where time went.
So that’s the lesson in this little thought experiment. What do I want from the years I have left? What might I look back on and wish I’d done that I’m not doing right now?