REWORK

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Don't write it down

Explore episode Jul 15, 2026
Business
Roadmaps create illusions of agreement

Don't write it down · Jul 15, 2026

A bullet point on a roadmap makes customers believe a future feature will solve their specific problem, when in reality the final shape of the feature may not match their expectations at all.

Where this was said

Why 37signals doesn't do roadmaps

At 9:54 · chapter starts 7:37

DHH introduces the concept from Getting Real: the illusion of agreement. A bullet on a roadmap says 'upload permissions' or 'guest access' — one line that customers read and project their entire mental model onto. The feature ships. It's in the right vicinity but has the wrong handle, the wrong shape, the wrong defaults. Now the customer feels suckered: they bought the product on a promise that never existed except in their imagination. Jason makes this visceral with the calendar example: announce you're adding a calendar, and every customer imagines their own perfect calendar. The one that ships won't sync with Outlook, won't have an agenda view, won't allow jumping four years ahead. Useless, they'll say — even though a fully functional calendar did ship. The word 'calendar' was never a promise about any specific capability; it was just wrapping paper. And the illusion, Jason observes, only grows larger and stranger as you move outside your own team: internal misalignment is bad enough, but external misalignment with customers who share none of your vocabulary or mental model is an order of magnitude worse.

Business
Why 37signals Doesn't Make Roadmaps

Don't write it down · Jul 15, 2026 Business

37signals plans roughly one month ahead and nothing more. Launching one feature opens trails to the next — rigidly pre-planning six months out kills that optionality. Basecamp's 22-year track record is the argument: if you're worried about uncertainty, look at the longevity.

Business
Roadmaps Are Illusions of Agreement

Don't write it down · Jul 15, 2026 Business

A one-line bullet on a roadmap means nothing. Customers imagine their specific version of 'calendar' or 'guest access,' while the final product takes a completely different shape. Buy software for what it is today — everything else is gravy.

Business
Forward promises always end in regret

Don't write it down · Jul 15, 2026

Every time 37signals has publicly promised a future feature on a timeline, it has ended in regret — not necessarily because the feature was wrong, but because the deadline was constraining.

Business
Forward Promises Always End in Regret

Don't write it down · Jul 15, 2026 Business

Every time 37signals made a public promise about a future feature, it ended in regret. Not always because the feature was wrong, but because the deadline crowded out everything else. Deferring a promise is a weaselly yes — if it truly mattered, you'd be building it right now.

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