OH: "Database design, including demoralisation."
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I'm a huge fan of Swift's 'Error Handling Rationale' design document: https://github.com/swiftlang/swift/blob/9315673c003875158852579bd1f33480cdec5461/docs/ErrorHandlingRationale.md#fundamentals
It carefully defines terminology and compares with other languages, so you can understand Swift's position and preference in the design space.
Exploring design ideas using AI as a learning assistant, for creative exploration: https://andymatuschak.org/hmwl/
@krinkle A surprising number of PL design workarounds are "just add another equals sign" 🙃