I’ve been thinking lately about what I regret, the way you do at this age, and the thing that’s surprised me is which regrets turned out to matter.
The things I did wrong stopped hurting a long time ago. The arguments I shouldn’t have had. The times I was short with someone I loved. The friendships I handled badly when I was young and didn’t know any better. Some of them I apologized for. Some I didn’t, because the person was gone or the moment had passed, or I told myself it wasn’t worth dragging back up. Either way, they’re quiet now.
What isn’t quiet is the rest of it. The friend I kept meaning to call. The trip my wife and I talked about for thirty years and never took. The conversation with my father that I figured I’d have eventually.
Those are the ones that wake me up at four in the morning, and I’ve come to understand they’re not going to resolve the way the others did. There’s nothing to apologize for. The thing just didn’t happen, and now it can’t.
I used to think the hard part of getting older was making peace with what you’d done. Turns out the harder part is living with what you didn’t do.
The regrets I apologized for stopped hurting a long time ago
When I was younger, I thought guilt was the worst feeling a person could carry. The thing you said you couldn’t take back. The choice you made that hurt someone. I spent a lot of years bracing against those.
What I didn’t expect was how much they’d quiet down.
I think about my first marriage sometimes. I was twenty-six when we married and twenty-nine when I left, and I left badly. I didn’t have the language for what was wrong, so I made it her fault out loud and mine quietly, and I moved out on a Saturday while she was at her sister’s. I’ve thought about that Saturday a thousand times. I wrote her a letter in my forties, trying to say what I couldn’t say at twenty-nine. She wrote back, kindly. We’re not in touch now, but the thing between us isn’t sharp anymore. It happened. I did what I did. I said what I could say. It’s quiet.
That’s how most of the things I did wrong have gone. They had an event attached, and the event let me work on it. The other kind doesn’t work like that at all.
It’s what I never got around to that still aches
The friend I’m thinking of right now is a man named Don, whom I knew from my first job out of school. Don and I were close. We played a lot of basketball. We talked about our girlfriends, and then our wives, and then his divorce, which knocked him sideways.
After the divorce, I didn’t know what to say to him. I let two weeks go by without calling, and then a month, and then I told myself I’d see him at the company picnic. He didn’t come to the picnic. I told myself I’d call him in the new year. I didn’t call him in the new year either.
We drifted, the way men do, by not picking up the phone. I’d think about him every few months, and every few months I’d tell myself I’d reach out, and I never did. He died in 2019. I read it in the alumni newsletter. I sat at my kitchen table for a long time with that newsletter open.
I never said a wrong thing to Don. I didn’t do anything to him. I just didn’t do the thing I should have done, which was pick up the phone in 1986 and say I was sorry his marriage ended and ask him how he was. And that not-doing is somehow heavier, thirty-eight years later, than most of the things I actually did.
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There’s no wrong thing to undo, just absence
This is what I’ve come to understand about the regrets attached to things I didn’t do.
They don’t have edges. There’s no event to revisit, no moment to apologize for, no specific harm I can name and try to repair.
There’s just a place where something should have been, and instead, there isn’t anything.
When I think about my marriage, I can point to the Saturday I left. I can hold that Saturday in my hand. I can be sorry about it. When I think about Don, there is no Saturday. There is a phone I didn’t pick up, and kept not picking up until 2019, when it didn’t matter anymore.
Research says it’s common that inaction regrets are harder to shake than action regrets because they stay open-ended—you can keep imagining what might have come of them. That’s exactly right. I can picture five different versions of the friendship Don and I might have had, and none of them happened, and all of them still feel real to me when I think about him.
Some of these doors closed while I wasn’t looking
I told myself these regrets were fixable. I’d call Don eventually. I’d have the real conversation with my father eventually. My wife and I would take the trip eventually.
My father died in 2007. He was eighty-four, and his death wasn’t a surprise, and we’d had a perfectly fine relationship for fifty years that nevertheless never included the conversation I’d been meaning to have with him, which was about why he’d been the way he was when I was a boy. I had decades to ask him. I kept thinking there would be a better moment. There wasn’t a better moment. There was a hospital bed in 2007, and I held his hand, and we talked about the Phillies.
The trip my wife and I planned for our fortieth anniversary didn’t happen because by then she’d had her first stroke and couldn’t fly. We’ve been married fifty-one years now, and the version of us that would have taken that trip doesn’t exist anymore. There are still good things, but that particular thing has closed.
This is what I wish someone had told me at fifty: the window on some of these closes without warning. You think you have time. One morning, you find out you don’t, and the thing you were going to do has become a thing you can’t.
Telling myself I’ll get to it now doesn’t work the way it used to
There’s a whole genre of advice that says when you notice a regret of inaction, the answer is to go do the thing.
Take the trip. Make the call. Write the letter while you still can.
I’m not against any of that. Where I can still act, I do. I called an old colleague last spring, whom I hadn’t talked to in fifteen years, and we had a long lunch, and I’m glad I did it.
But I want to be honest about what I’ve learned at this age, which is that a meaningful share of the list is no longer available to me. The person is gone, or I’m not the man I was when the thing would have meant something, or the version of the relationship that would have been possible has changed beyond recognition.
I can’t call Don. I can’t ask my father what I wanted to ask. I can’t take the trip with the version of my wife who could still hike. A younger person reading this can act on most of their inaction regrets, and they should. By my age, a real percentage of the list has aged out, and pretending otherwise is just another way of not facing it.
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The work isn’t finishing—it’s loosening my grip
I used to think the answer to regret was to close it out. Resolve it, fix it, finish it. That worked for the regrets I could do something about. It does not work for the rest.
What I’ve been learning, slowly and not always well, is something a piece on stubborn regret describes as the work of releasing them and moving forward. Not finishing them. Releasing them. The two are not the same.
Releasing is harder than apologizing. With an apology, there’s a thing you do, and then it’s done. With release, you have to keep choosing, every time the regret shows up at four in the morning, not to grip it. And it will show up. That’s what these regrets do.
Some mornings, Don is in the room with me. So is my father. I let them be there. I don’t argue with them anymore. I don’t promise myself I’ll fix it, because I can’t. I just sit with the fact that I didn’t, and after a little while, I get up and start my day. That’s the work, as best as I can describe it. Not finishing. Loosening.
Editor’s Note: “As Told to Bolde” stories are inspired by reader submissions, interviews, and accounts shared with our editorial team. Details are often changed, combined, or dramatized, and our editors use AI tools in the writing process. See our Editorial Policy.
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