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Steve McGarvey

Dear Younger Me

Ten letters, written as career judgment addressed to a younger self, with AI as the thread running through all of them. A different register from Judgment Under Constraint: personal, direct, warmer.

They converge on one conviction: judgment is built through time, under real conditions, not shortcuts. Read them start to finish, or pick the one that matches where you are.

  1. The Work Didn't Change. The Conditions Did.

    The framing letter for the series: judgment used to hide behind effort. Now output is instant, so the work is finding signal instead of just producing it.

  2. Imposter Syndrome Is Real. So Are Imposters.

    On telling the discomfort of not knowing yet apart from the discomfort of a gap you haven't closed. AI makes both feelings harder to tell apart.

  3. You Are Not Your User.

    You are not your user, no matter how much empathy or confidence tells you otherwise. On projection, distance, and where real evidence actually comes from.

  4. Sounding Right Is Not the Same as Being Right.

    A well-articulated opinion and a correct one are not the same thing, and AI makes that gap easier to miss. On naming where a claim actually came from.

  5. Fast Answers Hide Bad Questions.

    The faster an answer arrives, the more likely someone skipped the harder work of asking the right question. On protecting the space for inquiry.

  6. Good Work Doesn't Move on Its Own.

    Good work doesn't move on its own. Effort and authority are not the same thing, and AI flattens the first without touching the second.

  7. Your Career Is Not an Internship.

    No one is pacing your learning for you, and AI can hide that fact for a while. On owning your own development instead of waiting for permission.

  8. Clarity Is the Leverage.

    Clarity doesn't emerge automatically from good thinking. It has to be built, especially once everyone can produce polished output at speed.

  9. Hold Your Judgment, Not the Outcome.

    Disagreement is not a verdict on your value. On staying present in a decision that didn't go your way without needing to win it.

  10. Signal Is Harder to Find Now. That's the Job.

    The closing letter: judgment doesn't announce itself, it accumulates. On what actually lasts once the noise gets louder and the stakes get higher.