Here's what I suspect would actually happen if I could send a letter back: I'd agonize over what to say, write something carefully calibrated and wise, and my younger self would read it with mild interest, think "yeah, yeah, I get it," and then continue making exactly the mistakes I made. Maybe they’d have a few new anxieties about whether he was... See more

The advice that would actually be useful is the advice I couldn't have followed.

Would I tell my younger self about my current life?

That seems like it might work, at least as motivation. "Look, everything turns out fine! You get the things you want!" But I'm not sure that's even true in the way younger me would have understood it. I got things, sure, but not the specific things I thought I wanted. I wanted to be impressive in... See more

Fact: You can't skip steps.

You need a certain amount of accumulated experience, mistakes, and random encounters with ideas before new concepts can slot into place. Telling my past self to read certain books at the wrong time would be like trying to teach calculus to someone who hasn't learned algebra yet. The information would bounce off. Worse,... See more

And then there's the problem of specificity versus actionability. The advice that's specific enough to be useful ("don't date *Anna, it will end badly") creates weird paradoxes. If I don't date *Anna, do I still become the person who would later write this letter? The advice that's general enough to be robust ("be more honest with yourself about... See more

The problem was never information. The problem was that knowing things intellectually and actually integrating them into your decision-making are completely different processes.