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) s...

Tom Ruery

Tom Ruery