I'd do it again

09 Feb, 2026

I go too hard on myself. I have for most of my life, ever since I was old enough to hold myself morally accountable. In that context, it can be difficult to give myself credit for my achievements, especially past achievements that feel distant.

For example, I don't feel very proud about graduating high school. The person who suffered through to graduation was hardly the person I am today. I feel similarly about most of my past actions. "Maybe you deserved to be proud at the time, but what have you done lately, Dan?"

Last week, I realized one way to allow myself more kindness. No, I'm not still the person who was getting to school every morning despite terrible avoidant anxiety. Credit goes to past Dan. But I am still the person who would do that, because I did it then and I know that I'd do it again. That's the part my brain is willing to accept. If the present me were transplanted into the past, yes, I'd do it again.

The old pride

To see why I even need this sort of reframing, we have to back up to the first time my self-esteem shook. Allow me to set the stage: I was a smart kid. Not only that, I was a Smart Kid™. And believe me, I knew it.

Then, I grew up a little. I had just a few too many interactions with guys¹ who were proud to be smart, who morally valued their intelligence like a badge of high character. Think self-congratulatory MENSA types. Let me tell you, those were not my favorite guys. I had some sort of a reckoning around age 14, and my self-worth divested hard from my intelligence.

Reevaluating the roots of my self-worth was a choice, and something I worked for. Something I worked through, really. That's the sort of thing I'm proud to be proud of.

A too-rigid rule

I wound up with a tacit policy I've held for the rest of my life (so far): I'm allowed to be proud of things I do and choices I make when they take effort. I am not, however, allowed to be proud of the things I didn't work for.

The idea is to constantly expect that I do my moral best. I'm a hazardously authentic person who sticks to my values. I can look back, even at my Smart Kid™ days, and be proud of compassionate actions or whatever. The thing is, I don't. I only tend to judge myself on who I am now, what I've proven about my character lately. This philosophy has motivated a lot of moral growth, but it leaves me vulnerable to a spiral if, for whatever reason, I do anything I'm not proud of.

The past hasn't been holding enough weight. I could do ten little things I'm proud of and one I'm not, and by all means the ten should outweigh the one. But if that one is more recent, I won't feel that way. I'll feel like I was doing so well until the last second, and now I'm not as good a person as I thought.

This is stupid of me.

Synthesis

The goal is to give myself due credit for past actions. I want to get better at evaluating myself fairly, more like I evaluate others. Even when thinking about my current self, I should consider my past actions because they do say something about the present-day me I'm evaluating.

Maybe this should already have been obvious. The worry, though, was that I'd go too easy on myself because I had done a good deed, y'know, that one time. What if I become satisfied I've already hit some mark for moral success, and then I get complacent? What's to stop me from owning my past successes while excusing all my past faults? Won't I view my past self too compassionately, with the rose-tinted glasses donned for a relatable protagonist?²

To allow the wider lens, I'll have to keep my present self accountable. I should evaluate my past actions with respect to my current self. When I think about who I've been and what I've done, the question is this:

Would I do it again?

The question is really about the present, but the answer often lies in the past. Let's work a few examples on the board.

Would I bring my mom an ice pack?

When I was 2, my mom had a minor surgery. Apparently, I brought her a fresh ice pack. I don't remember doing that, and the person who did it was hardly the person I am today. My other parent probably had to help me fill the thing, but at least I attempted to help in my own underripe way. How should this impact my current view of myself?

On reflection, I am proud. I'm proud that even in the disinhibited haze of a toddler, I did something kind for my mother. It means more than doing the same under social expectation and with a clear mind. But the important question is, am I still a person who would do that for someone I love? Absolutely. Even in a fog, I would.

Would I train for a black belt?

I earned my black belt in karate³ near the end of high school. I trained for hours every week, sometimes every day, and had all the kata (choreographed forms) memorized. Good job, kid. But I forget most of it now. For years, I've been saying that I earned a black belt, not that I have a black belt or, heavens forbid, that I am a black belt. My form is probably still decent if I tried, but I haven't practiced seriously since college. I sure don't remember the kata.

High-school Dan was disciplined and persistent in a way I don't usually frame myself. What can I learn from that? Well, let's say I were in that situation again. Supposing I made a similar commitment, would I still have the discipline to follow through? I don't feel like someone who would, but I felt it even less at the time. So if I could do it then, I bet I could do it now.

Would I repeat my mistakes?

I'm not going to rehash this part quite so publicly, but I'm happy to share a few of my thoughts in case it helps someone else. I thought through a handful of my biggest regrets and shames. There are some my current self would definitely avoid. No, I would not do it again, thank you very much.

There are other regrets, though, where I'm not so sure. When I say that, I mean it very literally: I don't know if I could do much better. Admittedly, there's a bias here because my greatest regrets are the unresolved ones. I haven't retested myself against some of those pain points. I don't really want to.

So I'm going to do an experiment, and I encourage anyone reading to do the same. I'm choosing something uncomfortable to retry. Something disproportionately sore for its actual impact. Will I regret it like before, or will I do better? Too soon to tell, but at least I'll give it a real go. I can be proud of that much.

Footnotes

#reflection