There’s a genre of thought experiment that involves writing letters to your younger self.

You’re supposed to impart hard-won wisdom, spare your past self some suffering, maybe tell them to buy Bitcoin or avoid that regrettable haircut.

I’ve been thinking about what I’d write in such a letter, and I’ve concluded the whole exercise is doomed from the start.

My younger self wouldn’t listen.

Worse, if they did listen, they’d undoubtedly fuck it up in some other // alternative // novel and creative way I can’t even anticipate.

The problem with advice-giving in general is that nobody takes advice. Your mate asks whether they should break up with their mediocre boyfriend, you give them a thoughtful analysis of their relationship dynamics, and three months later they’re still together and complaining about the same things.

But the Blogosphere’s favourite “letters to younger selves” genre has a special kind of futility baked in.

You’re not just battling human nature’s foundational resistance to advice. You’re fighting the specific human nature of the person you used to be. And that is futility itself.

This is me: I was anxious in ways that made perfect sense to me at the time and seem completely insane now. I cared desperately about things that turned out not to matter at all, and dismissed as unimportant the exact things that would shape my entire adult life.

If I wrote to tell my eighteen-year-old self “that philosophy class you’re dreading will change your entire worldview, and that party you’re excited about will be completely forgettable,” they’d probably think I was lying or had become boring with age. They’d go to the party anyway, skip the reading, and feel vaguely guilty about both.

The advice that would actually be useful is the advice I couldn’t have followed. “Learn to notice when you’re optimizing for looking smart rather than being correct” is great counsel, but it presupposes a level of awareness that took me years to develop. Younger me was a glorious, wondrous idiot. Younger me wouldn’t have even understood what I meant. They’d have nodded, thought they understood, and continued doing the exact thing I was warning against, now with the added confidence that they’d already learned the requisite lesson.

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, premature exposure might have inoculated me against ideas I’d later need. I’ve seen people encounter ideas far too early, decide they’ve understood them, and then walk around with a cargo cult version that makes them more wrong than if they’d never heard encountered the concept in the first place. See: people who think they understand 1984, Marxism, capitalism and human behaviour at the salad bar.

And then there’s the problem of specificity versus actionability. The advice that’s specific enough to be useful (“don’t date *Annabelle, it will end badly”) creates weird paradoxes. If I don’t date *Annabelle, 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 what you want”) is functionally no different to a Hallmark platitude that everyone already knows and nobody knows how to implement.

Younger me had probably already heard some version of every useful thing I could tell them. The problem was never information. The problem was that knowing things intellectually and actually integrating them into your decision-making are completely different processes.

I think about the Litany of Tarski sometimes: “If the sky is blue, I desire to believe that the sky is blue. If the sky is not blue, I desire to believe that the sky is not blue.”

Eighteen-year-old me could have recited this perfectly while simultaneously and convincingly lying about whether they actually enjoyed their major, whether their friends were good for them, whether their study habits were working. The gap between knowing a principle and living by it can be...enormous.

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 ways that now seem silly to me, and I accidentally became decent at things I hadn’t even considered pursuing. If I described my actual life to my younger self, they might be disappointed. They’d focus on the things I didn’t achieve and miss the things I value now that weren’t even on the radar.

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 making those mistakes. Maybe they’d overcorrect in some direction that creates different problems.

The only advice that might work is the advice they were already halfway to figuring out. If I caught them at exactly the right moment, when they were already starting to question something, then a letter might accelerate that process by a few months. But the big realizations, the fundamental shifts in perspective, those seem to require their own timeline.

They need to be earned.

To some degree, they need to hurt.

What would I write? Probably something like this: “You’re going to be fine. The things you’re worried about mostly won’t matter. The things that will matter, you can’t predict yet. Try to be kind to people, including yourself. Pay attention to what you’re actually experiencing rather than what you think you should be experiencing. Good luck. You won’t take this advice, but that’s okay. You’ll figure it out eventually.”

Then again, the whole point of the exercise is to feel like you’ve learned something, to convince yourself that you’re now wise enough to give your younger self advice.

The letter is less about the advice and more about the distance. Look how far I’ve come. Look at all the things I understand now. The younger self who wouldn’t listen is proof that I’ve grown.

Which is fine, I suppose.

We all need our little rituals of self-reassurance.

Field Notes on Now.