Jason Caldwell

    Notebook

    Notes on design, craft, and building things that matter.

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    JMSKARTL
    1,500+ readers
    September 8, 2026

    Out of Jurisdiction

    Every study has a jurisdiction: a limit on what it can rule on. Most of the skill is knowing where that line falls.

    Design7 min read
    July 28, 2026

    Boiled Tofu

    Most of the strong opinions in any product org are a bad exemplar or a wrong context wearing the costume of a real finding. Before an experience becomes a verdict, work out which of three things you're actually holding.

    Product8 min read
    June 29, 2026

    Finish the Row

    Web software is never done. We've built a whole religion out of it. But nobody asks whether the never-done model is good for the people building it — and the answer is often no.

    Culture13 min read
    June 10, 2026

    The 51st Feature

    The competitor ships fifty features. So the plan becomes: we need fifty-one. But the market keeps rewarding the opposite — over and over, you find companies that ship less and win anyway. The question is why.

    Product11 min read
    May 20, 2026

    Customer Obsessed Is Not Customer Obedient

    At some point "listen to your customers" came to mean "do what your customers say." Customer obedience is order-taking. Customer obsession is caring about the problem more than the request.

    Product4 min read
    May 1, 2026

    The Luck We Edit Out

    When a product wins, we reverse-engineer a clean story — the roadmap choices, the focus, the execution. The luck gets edited out. But timing accounts for more than the idea, the team, and the business model combined.

    Product5 min read
    April 8, 2026

    The Mirage of Obvious

    "Make it more intuitive." Everyone nods. But intuitive for whom? "Intuitive" isn't something a design is — it's something that happens between a design and a particular person's history with everything else they've ever used.

    Design8 min read
    March 3, 2026

    Free-99

    I drive past two grocery stores to shop with Linda. I pay 20% more to ship with Peter. I trust a man who identifies screws by feel. Somewhere, a professor is drawing a red X through my decisions.

    Culture5 min read