Some apologies come instantly. Others linger for years.
A while ago, a friend of mine died unexpectedly, and a group of us descended on his hometown for the funeral. I was 26, and I remember thinking that what had happened was a mark of aging: my first friend to die, inevitably the first of many. That weekend was like a scene out of a movie: a group of college friends, many of whom had lost touch over the years, reuniting for the worst possible reason.
The night after the funeral, we had a primal scream of a party, just the six of us, a shout into the void that we, at least, were still alive. In one of those late-night confessional moments one of my friends had opened up to me about something personal and though the specifics were hazy, when I woke up the next morning, all of us sprawled out on the floor, I had the unmistakable feeling that I hadn’t reacted well—that in the chaos of it all I’d said something rude or inconsiderate, or just hadn’t received what he’d told me with the grace it deserved.
It was the kind of verbal mishap that tumbled from my mouth with some frequency in my mid-twenties, the kind of thing I normally wouldn’t have thought twice about, but the context here made it especially galling: the whole weekend had been deeply, uncomfortably intimate, one of those rare moments of almost superhuman togetherness, and I’d said something dumb and hurtful. And so the memory of it ate at me for years.
I’d thought that I would just casually apologize to my friend the next time I saw him, but we hadn’t really been close since college, and for unrelated reasons I didn’t end up seeing him or even talking to him for years after that. Eventually remorse grew inside of me to the point where I couldn’t ignore it anymore, and I sent him a lengthy email apologizing, one I’d drafted and re-drafted a dozen times.
And he wrote back to say that he appreciated the apology but that he had absolutely no idea what I was talking about.
I was reminded of this incident the other day because I once again found myself telling the story of my former, failed startup, as I’ve so often found myself doing lately, and I kept using the same phrase I always do when I talk about those days: “no regrets.”
Not only that, I said, I don’t just have no regrets by happenstance. No regrets is my philosophy. Of course, there are things I’d do differently if I could do it all over again, a million small decisions I might make the other way. But regret is just a story we tell ourselves. The truth of things is hopelessly elusive anyway, so you’re better off just picking the narrative that serves you best. And the narrative that serves me best about that period is that I have no regrets.
As it so happened, I was telling this story as part of a talk I was giving, and it’s easy to spout those kinds of pithy philosophies when you’re giving a talk. “Regret is just a story we tell ourselves” looks great on a slide in 72 point Futura Condensed. But as the days after the talk went by, I couldn’t shake the feeling that I don’t really live up to my supposed philosophy.
It’s true that I don’t second-guess too many of the choices I made as a founder. But the devil-may-care attitude that lets me walk away regretless from my many career foibles is hardly present when it comes to my relationships. There I do regret, deeply and continually, more than is good for me, I think. It’s not as though my past is unusually full of woe, or that I think I’ve made worse choices than most other people—it’s just that I tend towards rumination.
Whenever I find myself getting too caught up in those kinds of thoughts, I try to think about the story of my apology to my friend. Memory is a poor guide, and the memories we think we share with others are rarely as shared as they might seem. I’m still close with my college girlfriend, and there isn’t a single story from our relationship that we both remember the same way. Half of the things I regret probably didn’t even happen the way I think they did.
I’m not suggesting that the possibility of a faulty memory means we can let ourselves off the hook for everything we think we’ve done wrong. We usually know when we’ve really hurt someone, even if there isn’t universal agreement on the specifics.. But there’s no point dwelling on every last detail when we’re probably not even remembering all the details right in the first place. When we ruminate, we’re most likely ruminating over fiction. Fiction that’s based on a true story, perhaps, but still fiction.
So I’ll revise my previous claim about “no regrets.” I’m full of regrets, a million little regrets, a steady stream of them, like one of those restaurants that serves sushi on an infinite conveyor belt. Some of those regrets almost certainly didn’t happen the way I think they did. I probably regret at least one thing I didn’t actually do. So I try to keep them shallow—not deep wounds, but paper cuts. I accept the fact that in some ways, understanding the past is just as hard as predicting the future. And I’ll keep apologizing for the things I think I did wrong, whether the other person remembers them or not.
Yours in the knowledge that half of my future regrets will likely be the things I decided to disclose in this newsletter,
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