I keep a failure catalog. It’s the highest-leverage document I own.
One running file. Every time a system breaks — mine, a client’s, one I only read the postmortem for — it gets a line: what broke, what everyone believed right up until it broke, and what would have caught it earlier.
For years that file just made me harder to surprise. Then AI gave it a second job.
Now, before I design anything new, I hand the catalog to the model along with the proposed architecture and one instruction: tell me which of these failures this design is about to repeat. Pattern-matching across years of wreckage, in about a minute. It’s wrong sometimes. It’s uncomfortably right often enough that I’ve stopped skipping the step.
Experience isn’t the years. It’s the catalog. Most people live through the failures and keep nothing. Write them down, and even the machine gets smarter with you.