When I look back on my life, most of the memories that nag at me today aren't things I could call "regrets" in a typical sense of the word.
I think most people talk about "regrets" as things they did but understand they shouldn't have done—actions they were fundamentally mistaken in pursuing.
I've definitely done dumb things, but I try to be hold onto some compassion for the younger/dumber version of me. There are always going to be life lessons we end up learning the hard way. By understanding that our own mistakes and failures were just a natural and inevitable part of our development, we can let go of some of that inner cringe that can hold us back in the present, and (I think) learn to be kinder to others as we see them go through that same lurching growth process.
If you can't forgive the younger version of yourself for their faults, it's even harder to forgive others.
So, no, remembering various dumb things I've done in the past—looking back on past "regrets" in the way most people use the word—generally doesn't bother me much today. I try not to let myself get stuck in that mindset, at least.
The things that still bother me today, the memories I tend to dwell on, are actually those times when I was right about something important, but then found I couldn't do anything about it.
A very simple example might be when a friend of mine started a new relationship not that long ago, and it was immediately obvious to me that things weren't going to work out, and that my friend was over-committing from a place of insecurity. Well, okay—what do you do with that?
It's generally a pretty terrible idea to mettle in another person's love life directly; we all have a lot of our own baggage that we just sort of work through over time. It's also generally a bad idea to just try to "fix" people, telling them exactly what their core character weaknesses are, tempting as it might be. Usually the best we can ever do for our friends is just to be kind and supportive, and stay committed to that friendship through the ups and downs.
If there's any way to "win" in a situation like that, it's just to wait it out. There is no better salve for insecurity than persistent and enduring care.
But being able to sit and wait things out like that—that's exactly why the "thing happening with a friend" example is really too simple. When we're dealing with situations that directly affect us, waiting things out might not be an option.
Another, more intellectually honest example: any one of the jobs I've had where I felt like my team wasn't focusing on the right problems. We'll say a programming gig, to make things concrete. I look up from my computer at one point, realize our code quality sucks, we don't have a strong/cohesive vision for the product, and the individual contributors are all generally unhappy. What do you do with that?
You can try to agitate for change, but if you can't get real traction then eventually you're just someone who complains about everything and people already know how much the situation sucks; being a whine-y jerk is a good way to get fired, or at least make your teammates hate you. You can try to stick it out and hope things get better on their own, but then you're miserable all the way through, which can hurt your productivity and make it more likely that you piss everyone off and get the axe anyway. Even if you did stick it out, your whole team might get cut if things really are going as poorly as you think they're going.
Near as I can tell, your best bet in a situation like that is to quit as soon as possible. You want to try to preserve whatever nascent relationships you have there and just exit gracefully. But, speaking personally, I spent years being broke or nearly broke after high school, and so quitting wasn't an immediate option for me a lot of the time unless I had something else already lined up. The sense of entrapment in those situations can be overwhelming.
In chess, there's a game state known by the German term zugzwang, in which any move the acting player makes can only leave their position weaker. If they could just leave things exactly as they were, forcing the other player to move, then the game might play out fine, but chess (unlike go) doesn't allow a player to "pass" on their turn. You're compelled to act and can be left off worse for it.
The chess player's only recourse is to avoid getting into such zugzwang to begin with. There's a sense in which that state is only a realization of errors previously made, and the mechanics of the game force you to play through that realization.
A good chess player might recognize certain patterns that lead them to zugzwang, and proactively avoid letting themselves get caught in the same way they were drawn in before, the same way I'm now conscious of being mentally and financially prepared to gracefully exit any job that turns out to be a poor fit for me. But in life, unlike in chess, we don't start with a fresh slate and get to pick our own set up.
Something that I think about sometimes is just that I have (from what I can tell) a rather unusually fluid concept of gender. In fact, I'm a pretty strong adherent of Queer Theory, which broadly posits that what we call "gender" doesn't exist per se; rather, there are societal expectations of gender roles that we choose how to fill. That feels very intuitively real to me—much more real than more traditional (even earlier-wave feminist) concepts of gender—and I suppose that's fitting, as it seems inseparable from my lived experiences (romantic, sexual, and otherwise) as a bisexual man.
As a writer of fiction and poetry, I frequently play this a step further, "queer-ing" some character or subject of a piece by swapping their gender (or at least the pronouns) away from their real life counterpart, or even just the first image of that fictional person I had in my head.
... I don't tell anyone when I do that, and it's hard to know how I would, even if I wanted to. What would it even mean to anyone else if I did?
But the thing is, sometimes I do want to. Part of why I write is to find new ways of connecting with others, or at least to share my ideas in new forms. The thing that sucks about the really big concepts, especially many of the ones connected to core aspects of our identity, if that we are frequently too close to them to have direct conversations about them. They can act as close friends, positioned awkwardly in the middle of a conversation about them, rightfully refusing to be spoken over.
I'm still learning more ways to approach those conversations; I'm still broadening my arsenal of indirection, finding new ways to strike surprising and meaningful connection. But it's not clear to me that I'll ever find a way to say all the things I want to say, and truly be heard.
One other big difference between chess and life, of course, is that there are no inherent rules as to how we live our lives.
In chess, the game and its outcome have meaning because both players play within the standard confines of what we call "chess": the rook moves horizontally and vertically, the bishop diagonally, etc.
In life, however, we find meaning in the rules we choose to take up, the goals and restrictions we impose upon ourselves. I might never reach the perfect ease of connection with others that I want—certainly not on all topics—but it means something to me that I'm trying.
I don't look back through my memories for regrets; I look back at the tough situations I'm determined to face again, trying to find an edge I can press to my future advantage.
It's important to maintain a certain level of self-awareness with all these things in order to hold onto our core sense of agency.
One last thing I've been thinking about a lot lately—
Michael Lewis describing John Gutfreund in the epilogue to The Big Short:
"The same veneer of courtliness masked the same animal impulse to see the world as it is, rather than as it should be."
That "animal impulse" is a really essential thing in life, I think.
Lately I've been mulling over the fact that we don't have any selection criteria for American Leadership Foundation scholarships that would serve as even a rough parallel to that basic mode of operation. And that's a bit strange, maybe, because I'm not sure if it can be taught. I do think it can be learned, though, and so it's just another place where I'm hoping to figure out how to be as helpful as possible.