About

About

I didn't plan to be here — older than I figured I'd be, starting over in ways I didn't see coming. But here I am, and it turns out I'm not the only one.

I grew up in East Boston, working-class, the kind of place that makes you before you know it's making you. I've been a drummer, a writer, a husband, a father. I got sober decades ago and I've spent the years since paying attention — to what holds up, what falls away, and what nobody warns you about. I've buried people I loved and started over more than once. I'm not writing from the finish line. I'm writing from the road.

Older Than I Planned is exactly what it sounds like: an honest look at the second half of life. Not the glossy version where everyone's doing yoga on a beach and calling it their "best chapter." The real one — the part where you take stock, let go of some things, pick up others, and figure out who you are when the plan you had doesn't match the life you got.

I'm not here as an expert. I'm here as someone a little further down the same road, turning around to say: it's not what they told you, and it's not as lonely as it feels. Some of it's hard. Some of it's better than the first half. Most of it, nobody talks about honestly — so that's what I'm going to do here.

If you're somewhere in the second half and figuring it out as you go, you're in the right place. Pull up a chair.

— Jack

Great! You’ve successfully signed up.

Welcome back! You've successfully signed in.

You've successfully subscribed to Older Than I Planned .

Success! Check your email for magic link to sign-in.

Success! Your billing info has been updated.

Your billing was not updated.

© 2026 Jack St. Croix. All rights reserved.