How to Pick a Career (That Actually Fits You)

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TL;DR: Conventional wisdom sucks. Reason from first principles to pick a career for yourself.


  • “Typical” life path sucks. Everyone floats down the “river” with the same macro guidance, and then get spit out into the real world which is completely different.
  • It’s worth thinking about this stuff: a typical career will take up somewhere between 20% and 60% of your meaningful adult life
  • Options = intersection of yearnings (what you want) and reality (what is possible)


Yearnings: What You Want

  • Everyone has a personal yearnings octopus with all of their conflicting thoughts and feelings
    • Personal tentacle: why billionaires don’t just retire and do nothing
    • Social tentacle: obsessed with what people think of you
    • Lifestyle tentacle: just wants pleasure and relaxation
    • Moral tentacle: what kind of impact can I make?
    • Practical tentacle: oh shoot I have to pay rent
    • Human yearning is a game of choices and sacrifices and compromise


  • Dissecting yearnings: “Why? Why? Why?”…leads to a “Because”
  • Interrogate your yearnings to see if they are truly yours.
    • Do you treat the words of your external influences as information, held and considered by an authentic inner you, that you’ve carefully decided to embrace? Or are your influences themselves actually in your brain, masquerading as the inner you?
  • Prioritize your yearnings
    • You are what you do. Your priorities are easily observable through your actions.


  • As you prioritize, remember you are the only wise one in the room. You are the only one with the full picture.

Reality: What Is Possible

  • Yearnings help you figure out what you want. What you think you want is what you are in the habit of wanting, not what you truly deep down want.
  • Beliefs that dictate career possibilities:
    • Beliefs about the world
      • Today’s world goes through dramatic changes each decade, which usually leaves conventional wisdom wildly outdated. But we’re wired for an ancient world where almost nothing ever changed, so we all reason like cooks and treat conventional wisdom as equivalent to truth
      • Think critically about all of the possibilities! They are way more numerous than conventional wisdom would have you think.
    • Beliefs about your own potential
      • With enough time, could you get good enough at this game to potentially reach wherever your definition of success in that career?
        • Progress = Pace * Persistence
          • Pace: level of chefness, work ethic, natural ability
          • Persistence: how much time you are willing to commit to chasing
      • Conventional wisdom doesn’t get how non-traditional careers work – it only thinks in terms of a narrow aspect of successs: talent and hard work. When career paths have game boards with much more going on, conventional wisdom just throws its hands up and calls it “luck”.
      • Don’t think of strengths and weaknesses as snapshots of individual skills (e.g. dribbling a basketball). Rather, think of them as important signaling traits (stubbornness, work ethic).
        • Think in terms of potential for improvement
          • Ex: if you gave Michael Jordan a basketball at 25 for the first time, it would be wrong to call basketball a weakness under this framework
  • Take all these factors to build your reality box

Connecting the Dots


  • Your career is a series of dots. Connect those dots.
  • How do I know if I should move?
    • Ask yourself truly deep down what doubts you have.
  • Goal: not happiness, but contentment: feel like you’re currently taking the best crack you can at a good life path.
  • Summary of post:


  • Final thoughts:
    • It’s when we feel too good that we run the risk of becoming overconfident, intellectually complacent, and set in our ways. It’s exactly when we think we have life all figured out that we end up losing our way.
    • The mistakes that bother me most are the ones that happened because someone else tookt he wheel of my head and overruled the quited, insecure voice of my authentic self – the mistakes that I knew at the time, deep down, were wrong.


  • Drier than most WBW posts but still engaging and of course informative
  • Always seems to put into words things I’ve thought for a long time. Nice.
  • Did not trigger as much existential dread about my own career choices as I thought it would. Still quite happy about software development/entrepreneurship/machine learning as things I work hard at and enjoy.