CLOSING — LATE LETTERS
32. Sunday Morning Thoughts
"Certainty, it turns out, is often just inexperience in disguise."
This is the last of the letters, and I wanted to end not with a grand conclusion but with a slow morning and an honest admission — that the older I get, the less sure of anything I become. A few years ago, I was living in Southeast Asia, stuck in a role that didn't fit, surrounded by circumstances I wanted to escape. I kept a mental list of everything I thought would make me happy: a company of my own, friends I could talk deeply with, the freedom to work on things that mattered. China felt like the answer. I was certain that if I could just get there, things would be different.
Today I'm in China. I have the company. I have those friends. I got exactly what I wished for. And sometimes I catch myself daydreaming about Southeast Asia — the wandering, the uncertainty, the freedom of not being anchored anywhere.
It's easy to assume the things you want will make you happy. They might. But rarely in the way you imagined, and never as completely as you hoped. The grass-is-greener effect doesn't go away once you reach the other side; it just points you back to where you came from. Maybe happiness isn't about arriving somewhere. Maybe it's about having the option to move, even if you choose to stay.
When I think back to those years in Southeast Asia — the ones that felt heavy and confusing at the time — I notice something strange. I remember them fondly now.
Rose-tinted glasses are real. Whatever you're going through that feels impossibly hard probably won't feel that way forever. You'll look back with a warmth you can't access in the moment. The difficult chapter becomes a good story. The uncertainty becomes adventure. The struggle becomes character — I wrote you a whole letter once about the golden years that didn't feel golden while I was living them, and this is the same truth, arriving quietly a second time.
The problem is that this knowledge doesn't help when you're in it. If I could send a message to my past self, it would just be: things will work out. But I also know that message wouldn't have landed. When you're in the middle of something difficult, reassurance from the future doesn't mean much.
I didn't have a five-year plan. I didn't grind toward the life I have now. I just held a few wishes somewhere in my subconscious — vague images of what I wanted — and kept moving. Most of them came true. I don't fully understand how.
Steve Jobs said you can only connect the dots looking backward. I think about that when I get anxious — when I want to see tangible results now, when I worry I'm not working on the biggest and most important thing. But the path is rarely visible while you're walking it. You can't see how the dots connect while you're still drawing them. The best things often come from directions you didn't plan for. You don't always approach the mountain from the front. Sometimes the side path is the one that gets you to the top.
Over dinner recently, my friend Angelo asked me: "Do you believe in God?" I braced for a theological debate. Instead, he talked about gratitude. His point was this: having something larger than yourself to rely on — God, the universe, whatever you call it — means you can take your hands off the wheel sometimes. You don't have to carry the full weight yourself. You can trust that things will work out.
When I was younger, I was certain about everything. No higher power. Pure rationality. I thought confidence was a sign of intelligence. But here's the irony: as I've gotten older, as my thinking has sharpened, I've become less sure about the world. Not more. When you're young and inexperienced, you think you're right about everything. When you gain wisdom, you realize how much you don't know.
Certainty, it turns out, is often just inexperience in disguise. The older I get, the more I'm learning to let the world surprise me.
December 2024