Jason Caldwell

Notebook

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

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JMSKARTL
1,500+ readers
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