Letting Them Find Their Way…
Now it’s my kids.
Twenty-five. Twenty-three. Twenty-one. All standing at that awkward, unsteady edge of adulthood, trying to figure out who they are and where they’re going. Watching it stresses me out more than I care to admit. I want clarity for them. Stability. Forward momentum. A clean, sensible path.
And yet.
When I look back on my own early twenties, I was an absolute mess.
I was figuring it out in real time, making dumb mistakes, second-guessing everything, and thinking every decision was permanent when none of them were. And somehow, that period—the confusion, the uncertainty, the chaos—is one of the most fondly remembered stretches of my life.
I want that for my kids. Not the suffering, exactly—but the right kind of struggle. The post-college figuring-it-out years. Eating way too much cheap ramen and taking jobs that aren’t great but teach you something anyway—making choices that feel huge but turn out to be stepping stones.
After college, I lived at home and worked a truly crap job while studying for the LSAT. Then I moved into the city, went to law school, watched a lot of Mystery Science Theater 3000, drank martinis, and dated a girl who was all sorts of wrong for me. I hung out with Dave—who went to a different law school but whom I’d met at that awful job—and we stumbled our way through our twenties together.
Then there was the same wrong girl, but also weekends golfing with coworkers, wandering through shops in Wrigleyville, and what I now recognize as one small adventure after another. At the time, it didn’t feel magical. It felt uncertain. Unsettled. But looking back, it feels cinematic—like a live-action Richard Linklater movie where nothing much happens except life itself.
I don’t want to deny my kids that. I don’t want to rush them past the messy middle just because it makes me anxious. I want to be mindful—more mindful than my own parents probably were—that this phase isn’t fun while you’re in it, but it becomes meaningful with time.
So I’m here. To support them. To worry quietly. To trust the process even when it makes me uncomfortable.
And I’m also here to keep making memories of my own.
For most of my life, I’ve been able to look at whatever stage I was in and say, This is the best one yet. Somewhere along the way, I lost that perspective. I don’t want to stay stuck there.
My kids are becoming who they’re meant to be. I’m still becoming who I’m meant to be too.
I need to get back to believing that this—right now—is still the best chapter yet.