Forethought? I've never even had 1 thought

On trying new things, drive, and motivation

I’m typically a pretty stubborn person. I cite stuff like Naval saying, “I don’t want to read a million books. I want to read the same 100 great books over and over again”. I’ll take stock of my friendships each year and try to keep the people I want around close and focus less on everyone else less. I talk about how I like where I’m at, know who I want to be, what I value and it’s all about tending to my garden now.

All that is kind of bullshit though when applied to the max. I think much of it is valid— having close friends does make me incredibly happy, reading the same influential material does help reinforce what I think is important. But sometimes I feel like I’m conflating having strong beliefs with stubbornness. The goal is to have strong beliefs, loosely held. To both explore the world and exploit what I like in a constant loop.

But I’m not sure if there’s a point where I’ll be able to stop the loop — when will I be settled enough to not want to explore anything again? When will I have acquired enough “Good Things™️” that I won’t want to look for any more? I’m not sure if stopping the loop is even the goal, because it’s exhausting yet rewarding. Is the pain worth the pleasure?

My current hypothesis is it’s really not that deep — maybe someone with better epistemic thinking than me can reason otherwise, but now I just go based off of how I feel. I’ll have periods of expansion in my life where I’m incredibly prone to trying new experiences and meeting new people. Then periods of contraction where I like to stay close to what I like, prioritize existing friendships over developing new ones, and reinforce my roots by engaging more with stuff that “felt right” during my expansion period.

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The enemy of learning is thinking that you know something. All the smartest people I know really understand what they’re good at and what they’re lacking in, and are the first to say “I don’t know” when they don’t.

But what about when you don’t know what you’re lacking in? Like you feel like everything is pretty much going right and there’s no problems to work on? I obviously have problems, but overall in life I feel like this is the most stable period I’ve ever been in and I’m not used to it at all. Before this, my life felt like 20 years of mistakes, and I was always trying to fix my problems.

But after achieving a certain level of Okayness, and confidence that I could make good from mostly any situation, I am now in really unfamiliar territory.

For the first time in my life, nothing’s really wrong.

My brain keeps trying to convince me something is. I’ll have a small anxiety pang every now and then, and there’s still a million things I haven’t done, I do often get a sinking feeling that something could go wrong in the future and I’m waiting for the other shoe to drop and all that. But whenever I’m slept, showered, fed and watered, looking at my life objectively, I feel better than I ever have.

It’s going to sound crazy but there’s almost a soft of comfort in having big problems. You know exactly what to work towards. It’s like being given a list of tasks as an employee at work — no need to think about what’s important to do and why, it’s just your job to execute. But now I feel like I’m a manager, where I really have to think about my broader goals and plan what to do accordingly, and that’s way tougher cause a) it’s much more abstract and there’s no real right answer and b) I’m not used to this sort of big picture planning since everything was so task oriented before.

My life used to look like:

Problem #1: You don’t have any money and you need money to live.

Solution: Work on making money and save up so you can do what you want.

Problem #2: Canada sucks, there’s some cool people here but for a couple reasons it’s not the best place for you to live forever.

Solution: Get out of Canada. Get a visa and move to SF.

Problem #3: You’re lonely and have no good friends.

Solution: Do things you like around people, meet more people, work on being yourself around them, and stay close to people you feel good around.

But now, it’s more like:

Problem: ???? Nothing is obviously wrong but it’s always possible to be better and life is long so you should probably do stuff so you gotta figure out what you want to do.

Solution: 🤷‍♂️

The periods of my life where I’ve felt like this, I figured out what to do just by doing some random stuff and seeing how I felt about it. But it’s almost like the more I’ve done, the more I expect myself to do, and so before when I could just try things with nothing to lose, now I expect myself to really commit to the next thing I choose. It has to be THE thing — otherwise I’m just wasting time doing stuff that doesn’t matter right?

Sometimes all these thoughts feel overwhelming but I anticipate that this, too, shall pass. One day I’ll just start doing things again without thinking about it, and this natural period of ease and stability is needed in my ongoing sprint → rest lifecycle.

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I’ve been describing to some friends recently how I feel like I’ve changed immensely over the past 2 years. That I feel like a completely different person — not someone else, but who I always was, and these past 2 years have just uncovered more of him underneath the masks I developed in my youth.

I’ll say something like:

It’s like there’s a new CEO in my brain who’s been in charge for the past 2 years. But the former CEO is still around and got demoted to a VP and he’s grumpy about it. And the former CEO was around for 20 years so the new guy sometimes listens to him cause he brought the company this far and feels pressured cause the old guy is so stubborn. But the new CEO is here for a reason, because the same guy who built a company isn’t necessarily the same person fit to grow it.

In most ways I’m not actually that different at my core internally. I do feel like I’ve always been this way but I realize the outer didn’t always match the inner. I always thought I looked good in my head, but these past 2 years my physical health improved a lot and I finally match that inner expectation. I bought new clothes to bring the inner outside. I moved to SF since that’s a place I always felt like even though I was making the same jokes, people laughed harder. I told the same stories but people listened more intently. Everything that made me weird in high school made me cool in SF.

And in some ways that’s frightening, since I still sometimes censor myself expecting some sort of rejection to happen if I say or do what I really want, but it doesn’t. And that’s unexpected. And unexpected is scary. And so in some ways, it feels like everything I’ve known has been for nothing. Instead of learning and moving forward, it feels like all I’m doing is unlearning to stay where I am. I know I am still moving forward, and that unlearning itself is progress, but it’s almost like I have a debt to pay off, to unlearn everything holding me back, before I can move forward at the pace I want to. And that staying still is the “stability”.

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I’ve been thinking about how the 20 years of mistakes I made are what led me to this point of feeling so good. I love being right so innately I always had a fear of making mistakes. But my life got way better when, irrespective of the outcome, I just started trying stuff. I think my fear now is moreso that 'I’ll make the same mistakes, that I haven’t actually learned from them and am still as dumb as my 16 year old self.

When I’m at my best, I actively try to make new mistakes. I’ll run little experiments on myself like “oh, sleeping at 5 am makes me feel like trash, what if I just don’t sleep at all and then reset my schedule going forward?”¹ And I’ve done that before — it was a bad idea. But I realized what I was currently doing wasn’t working, and so even if I tried something else and it didn’t work, it couldn’t really get much worse than where I was currently at.

I spent 20 years in Toronto and just didn’t feel great — after my last job ended, I didn’t know what to do. With no income source I spent 4 months in SF, just cause I felt good while I was there. Left for 2 months, came back, ended up moving there permanently. I didn’t know I’d find a job I love and friends that feel like family along the way. I just knew that something I was doing wasn’t working and that I wanted to be in San Francisco — worst case I’m back in Toronto living with my parents where I started. If moving to SF was a mistake, so was living in Toronto. At least it was a new mistake.

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If I think about my motivation over the years, a lot of it was based on dark energy. Proving to people in high school that I would “make it”. Proving to my mentors that they were wrong about me being lazy. Proving to the girls that rejected me that I actually could be attractive and successful. Proving to my parents I didn’t need a college degree to be successful and stable. A lot of it was vengeance based, and driven by my inferred expectations of other people.

That dark energy is still within me, and I worry about it from time to time, but many of my major moves in the past year have been driven by light, love, and hope. Life became a little lighter after I spent less time alone guessing the thoughts of the people around me and instead spending more time with them trying to learn about their inner worlds. I started thinking less of them in relation to me and more about them as people with their own lives, doubts, fears, hopes, and dreams. Which has led me to think about myself from my POV rather than how others may see me.

Since doing that, I feel like my drive has actually lessened. I feel like I’m coming to a point where I don’t do nearly as much as I did, and yet I feel more satisfied, stable and happy than I’ve ever been by an order of magnitude.

Unlike I learned as a kid, life is not just about doing things and looking back on the list of things you’ve done and feeling happy or sad based on how little or how much you’ve done. I have friends who accomplish incredible things yet are still down on themselves and don’t even appreciate the things they’ve done nearly as much as I do or the world does, so that really can’t be it.

At my best moments this year (about 60% of the time) I find myself in a good, happy state — and whatever I do whether the world sees it as big or small, important or useless, good or bad — I take into account my judgement the most, which was almost never true before this year. I’m still fighting the war in myself of trying to get better everyday just for my own pleasure vs. showing my growth to prove to the world I have value, but this year I’ve finally been winning more just by looking inwards and asking myself if I’m pleased.

I still love doing stuff — there’s no drug like learning. But this year I learned a bunch of stuff that my 16 year old self would call useless yet be secretly really happy about and interested in if he met me today. Guitar, Chinese, mechanical engineering, writing, making videos — all this stuff I’m an incredible novice at but it brings me so much joy having tried it. I’m so proud I made the world a bit bigger for myself rather than sticking to my silo of being a really rich computer person, which is all I thought I was meant from from 16-20.

Now I have no idea what I’m meant for. I don’t feel the need to find out.

I just want to bathe in the possibilities

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Thank you to 柯凯琳 without whom I wouldn’t write anywhere close to as much as I do now. And for making me feel good about the stuff I think isn’t good enough (like this blog post initially).

1. I’ve experimented a lot with my sleep. Currently I find I’m best sleeping about 8-9 hours uninterrupted between about 1-10am. I’ve set up my life around this — as in I know I’ll never be able to work a typical 9-5 while feeling fully rested and maximally productive. So I usually work from about 12-6 and 10-12 and have felt the best working at jobs that don’t care when I work as long as I drive output.