I read Ryan Holiday’s “24 Things I Wish I Had Done Sooner (or my biggest regrets)” and thought I’d steal adapt the format; I wrote these quickly, with the goal of getting out answers—sort of like “Influential books (on me, that is).”

* Not trying to have kids sooner—much sooner.

* Not fundamentally growing up sooner—much sooner.

* Wasting time in humanities grad school (this is identical to the second point). It was fun at the time but the opportunity cost was so, so high.

* Student loans (which is also related to the second point). Not realizing that large parts of the higher ed system are powerful, important, and legitimate, but large parts of it are scams. Schools themselves obfuscate this basic point, which now seems so obvious to me; despite how obvious this is, no one cares enough to fix it. The student-loan system means schools have no skin in the game and incredible incentives to get students in the door, but no incentives to care what happens after they graduate. This is bad.

* There are lots of things that no one cares enough to fix, or that have established interest groups preventing fixes, and sometimes that’s just how the world is. Bullshit often wins, but it’s a mistake to let it win in your life.

* Not being able to connect normally with other humans (a family failure and one that, when young, I couldn’t even identify, let alone rectify). Diagnosis is a critical part of improvement and it took me way too long to diagnose some of those underlying problems. This regret is linked to a lot of other ones.

* Choosing what I rightly perceived to be the easy way with work.

* Short-term priorities over long-term ones.

* What matters long term? Family and people.

* What doesn’t? Stuff you buy. Status of a shallow sort. Whatever you imagine other people think of you (it doesn’t matter; all that remain is how you make them feel).

* Not knowing about or accessing the power of psychedelics. For a long time I imbibed and accepted the ’60s or ’70s narrative that psychedelics were for losers and could make you go mad. Michael Pollan’s book How To Change your Mind was essential here.

* Being afraid to be a beginner again.

* Chasing the projects of youth too far and too long.

* Being overly accepting of the “age is just a number” idea. There’s some truth in this saying, but a lot of cope, and it’s possible to get the truth without the cope. Most of us prefer the cope, however.

* There’s a lot I can’t control—including most things—but I can control my attitude. If I choose to. The “choosing to” is hard.

* You’re the sum of the five people you’re closest to and with whom you spend the most time. So choose well. I’ve often not.

* Smart, competent people congregate in particular places, and I wish I’d spent more time in those places and less time not in those places.

* Pretty much no one accomplishes as much alone as they do in groups dedicated in common goals and mutual improvement. I’ve spent a lot of my life searching for and not quite finding those kinds of groups, which makes me think about what I could’ve done differently.

* In different times and places, different important things are happening. I got overly interested in the dying dregs of literary culture, and have underinvested in what’s uniquely happening now. There’s still some utility in literary culture, but there’s a lot more elsewhere.

* You can’t do two things at once and multitasking is closer to no-tasking. Pick whatever you’re working on and ride it out. Cultivate flow.

* Some people are not going to get it and need firm boundaries. When you, or I, identify those people, pick the boundaries and hold them. The people who don’t get it also often least understand and respect boundaries.

* Life’s complicated and people have all kinds of things going on. Whatever people are doing probably makes sense from their perspective. Which doesn’t make what they’re doing right, but it may make it comprehensible.

* I don’t regret time spent building, making, and doing things. I do regret excess time passively consuming, particularly video.

* Habits compound. Including bad ones. The bad ones I regret, although I won’t list them here.

* Impatience with the right people is really bad. So is losing one’s temper with the right people.

* Incentives matter.

* Abundance is good and scarcity bad. Work towards abundance but don’t be ruled by material things either.

* No one, including me, gets to the end and is happy about staying on top of email. But don’t totally neglect logistics either. They have their place, typically at the end of the day.

* The people who win are the ones who love and master the details. And the ones who master the right ones. I too often mastered the wrong ones (like the aforementioned investing in the dregs of literary culture).

* Something else I don’t regret, and a common pitfall avoided: wasting a lot of time on “social” media, TV, and other forms of semi-addictive junk. I’ve made mistakes

* Being mean when I didn’t need to be, which is almost all of the time.

* Understanding that tact can, properly used, enable directness.

* Not looking into that thing on my tongue in July 2022, when I first noticed it, but that is very specific to me and probably not generalizable.

Reading through these, I realize that a lot of them are more about my generation than me as an individual: I made a lot of the same dumb mistakes a lot of other people made. When I was young, I thought I was different, and totally in control of my own destiny—and everyone else probably thought so too. And yet it turns out that I erred in extremely common, boring ways.