Dear Self; we need to talk about ambition

By Elizabeth @ 2023-08-30T18:58 (+66)

This is a linkpost to https://acesounderglass.com/2023/08/26/dear-self-we-need-to-talk-about-ambition/

I keep seeing advice on ambition, aimed at people in college or early in their career, that would have been really bad for me at similar ages. Rather than contribute (more) to the list of people giving poorly universalized advice on ambition, I have written a letter to the one person I know my advice is right for: myself in the past.

The Letter

Dear Past Elizabeth,

Your life is, in some sense, a series of definitions of success. 

First you’re in early school, and success is defined for you by a handful of adults. You go where they say, do the assignments they say, when they say, and doing well means meeting the goals they set for you. Even your hippie elementary school gives you very few choices about life. You get choices in your leisure activity, but that (as they have explained to you) is leisure and thus unimportant, and there’s no success or failure in it. 

Then you get further in school, and the authorities give you some choice over the hoops you jump through. You can choose which book you write your report on or even what classes you take (within a predetermined set). This feels like freedom, but you’re in still a system someone else designed and set the win conditions for. You can fulfill a college distribution requirement with any history class at all- but you are going to take one, and the professor is the one determining if you succeeded at it. 

More insidiously, you’ll like it. Creating your own definition of success feels scary;enacting it feels impossible. The fact that school lays out neat little hoops for you to jump through is a feature.

Work (you’ll be a programmer) is where things get screwy. Programming contains multiple definitions of success (manager, principal, freelancing, development, testing, bigtech, start-up, money-maxing, altruistic projects…), and multiple ways to go about them. If your goals lie outside of programming altogether (art, parenting, travel..), it’s relatively easy to work out a way to fund it via programming while still having the time to do what you want. Not trivial, but have you seen what people in other jobs go through? With programming it’s at least possible.

But you like hoops. You’re comfortable with hoops. So you’re going to waste years chasing down various definitions of success within programming, and by the time you give up will be too exhausted to continue in it at all. I think you (I) should have considered “just chill while I figure shit out” much earlier, much more seriously. It was reasonable to give their way a try, just due to the sheer convenience if it had worked, but I should have learned faster.

Eventually you will break out of the Seattle bigtech bubble, and into the overlapping bubbles of effective altruism, lesswrong, and the bay area start-up scene. All of three of these contain a lot of people shouting “be ambitious!” and “be independent!”. And because they shout it so loudly and frequently you will think “surely, now I am in a wide open world and not on a path”. But you will be wrong, because “be ambitious (in ways the people say this understand and respect)” and “be independent (in ways they think are cool and not crazy)” are still hoops and still determined by other people, just one more level meta.

Like the programming path, the legible independent ambition path works for some people, but not you. The things you do when pushed to Think Big and Be Independent produce incidental learning at best, but never achieve anything directly. They can’t, because you made up the goals to impress other people. This becomes increasingly depressing, as you fail at your alleged goals and at your real goal of impressing people. 

So what do we do then? Give up on having goals? Only by their definition. What seems to work best for us is leaning into annoyance or even anger at problems in the world, and hate-fixing them. 

You’ve always hated people being wrong, and it turns out a lot of things can be defined as “wrong” if you have the right temperament. Women’s pants have tiny pockets that won’t fit my phone? Wrong. TSA eating hours of my life for no gain? Wrong. Medical-grade fatigue? Wrong. People dying of preventable diseases? Extremely wrong. And wrong things are satisfying to fix.

A nice facet of this approach is that you can start small and it will naturally grow over time. Pocket extenders might give you a nice efficacy high at first, but soon you’ve built a tolerance and are taking on bigger and bigger wrongs just to feel alive. And you have more energy for that effort because of the problems you fixed earlier. 

A year ago I got really mad that people were becoming vegan without paying any attention to nutrition and decided to do something about it. That stopped being fun like a week in and was mostly a miserable slog. People yelled at me for doing it, which was pretty unpleasant. I was constantly on the verge of giving up but they were so wrong I couldn’t let it go. And then it ballooned into something huge. 

[Author’s note: The vegan epistemics sequence isn’t done yet. I kept finding one more post I needed before the big one, and eventually ran into a time-consuming commitment that ate my entire July and August. I hope to wrap this up soon, and I’m confident that something will be coming in the next month, but can’t rule out another 5 just-one-more posts.]

The spite-based path to impact and altruism is not the easiest road. Spite is a less fun emotion than hope, and makes fewer friends. But I also can’t bring myself to wish I didn’t have this drive, because it is my actual value system. Not caring if people destroy the commons would be easier in many ways but then the commons would be destroyed and that’s worse. 

It does seem good to have the option to be motivated by hope and not just anger-at-wrongness, and I’m experimenting with that now. I think it is working, but I don’t think I could have done it without the previous, spite-based projects.

Some specific advice

The following are a few tips I think might be generally useful as you think about how to spend your time. 

Plans don’t have to route through employment 

You’re never going to love programming. Trying was probably the right thing to do at the time, but I think you should have given up faster. Giving up would have been easier if you’d separated giving up on loving programming or succeeding in the career from funding your life via programming. You could have had many years of rest and vest if you’d been open to it. 

Would your life have been missing something? Yes. Was programming ever going to provide that thing? Not directly. But the free time and savings sure were helpful in the pursuit. 

Ways to identify fake ambition

Sometimes it’s hard to tell if you authentically want something, or are trying to impress people with how ambitious you are. Here are a few tricks I’ve picked up for distinguishing them.

1. What do you feel when you think about shrinking the project?
   1. Anger, fear, or disappointment that the goal won’t be accomplished = seems like you care a lot, good sign for the project. 
   2. Relief = project seems like a lot of work. Consider if you’re up for that level of work before beginning (but the answer might be yes).
   3. Fear of failure = this is a terrible sign, unless you have some reason the smaller version is more likely to fail (if you do, try the question again with a version that is easier and more likely to succeed). If failure feels like a bigger threat for a project that is objectively easier, that’s a suggestion you are, on some level, not taking the big version seriously. If you were, it would be scarier.
   4. Fear of other people’s reaction = your primary motivation here is probably social. Knowing that, do you still want to go forward? The answer can be yes, although if so I hope the project is cheap.
2. If you fail, will you or the people around you go “well what did you expect?” That would suggest your goal is unachievable from your current state.
   1. Another reason smaller projects can be scarier is that people will judge you more for failing. Don’t let this push you into too-big projects.
3. If you fail, will it be educational? “No” is both a sign the project is too big (because you don’t understand it well enough) and a reason the project is too big (you’re going to pour all that energy in and not even get learning out?)
4. How does concrete, accurate, actionable criticism make you feel? If it’s a real goal you should be delighted, because feedback helps you reach that goal faster. Or if you’re a little less evolved, not delighted, but at least it feels like a really productive massage or workout, where it hurts but you can tell it will be worth it. If you feel terrified, or angry, or especially unsupported, that suggests you care more about the social aspect of the project than its outcome.
5. Does the project give you a satisfying feeling of contact with reality? That’s maybe a sign it’s a real goal, and definitely good in general.
   1. What does “contact with reality” mean? That is a very reasonable question I don’t have a good answer for, at least not in words. Hopefully you’ll know it when you see it.

Some of the people talking about ambition and independence mean it

You will never impress them until you give up on doing so.

One friend in particular got palpably more respect for you 5 seconds after you gave up on impressing him. Not “dismissed as irrelevant” or “overcame your need for” his approval, just “accepted the reality that it wasn’t going to happen and stopped putting energy into it.” 

I could end this story with “…and then eventually you did real things he respected a lot” but that’s kind of like telling people it’s fine to not worry about their weight because chilling out will cause them to lose weight. It’s sometimes true, but if this is going to work it needs to not matter. 

Comparison is the thief of joy until you find the right reference group

Respect from other humans is a fundamental need, and I don’t want you to attempt to live without it. I just want you to have an accurate scale. Luckily, life is going to provide one for you that you can live with.

I spent a lot of time in the bay area feeling stupid and lazy. This got worse and worse until I went to Andy’s wedding in 2018. Andy, while quite ambitious in his hippy way, was about as far outside the bay area ambition bubble as you could get.  During the reception I had a flash of insight that I only look stupid and lazy next to the brilliant and driven people I deliberately sought out because I am smart and kind of driven (but not as much as them). Next to Andy’s hippy friends I am a titan of industry.

This felt like a socially unacceptable cure for anxiety at the time, but I talked to Andy about it a few years later and he said “oh yeah, it’s always been clear you were the friend of mine most likely to be remembered after you die”. Which is is a pretty intense thing to say, and honestly kind of weird because at the time you met his hippy goals definitely outscaled your programming goals. But he definitely wasn’t mad.

I don’t want to lean too hard on this. The point isn’t “I’m better than them because I’m ambitious”. They’re living their own best lives that wouldn’t be improved if I started shouting at them about ambition or the glorious fight for epistemics. It’s just that I’m not failing all the time.

Sometimes procrastination is a workers’ strike

If you just don’t seem to be able to focus on something, consider that you might not actually want to do it and you should quit. Better yet, get curious about why you don’t seem to want to work on it, with “I hate it and want to quit” being one of many options. This will save you a lot of time and misery. 

Your taste will always exceed your ability

…which means things you make will always be disappointing relative to the image in your head. People will tell you the cure is to push through and do lots of stuff anyway (my favorites). There’s definitely something to that, but I have this nagging feeling that that’s only half a cure. It looks to me like “stop thinking and just ship it” is as much of an avoidance strategy as “you can’t ship things until they’re perfect”.

Every once in a while I ask the internet “hey, how do you tell when to release subpar work and when to keep improving?” and no one has ever given me a satisfactory answer. Hopefully I’ll have something for you in a few years.

Conclusion

You should give “let other people set your success criteria” a good shot. When it works it’s way easier than creating your own. But you should recognize when you’re doing it (even if one of the success criteria you’re trying to meet is “be independent”), and when it doesn’t work you should move on. 

Best of luck,

-Elizabeth