That moment when you find yourself reading LLVM IR to work out what your compiler did. Is that a sign of a difficult bug or poor tooling?
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Bril is a cute intermediate language for teaching (think simplified LLVM IR): https://www.cs.cornell.edu/~asampson/blog/bril.html
The idea of providing a standard JSON format to help students write basic passes is really elegant.
I find it fascinating how some businesses have scheduled downtime for their websites (e.g. my electricity provider last weekend), but others don't.
I suspect it's primarily culture. You generally need to turn off electricity to do work, so your other tooling may reflect that.
An ad hoc, informally-specified, bug-ridden, slow implementation of half of a text adventure game -- or as I like to call it, a compiler.