I've sat on both sides of the handoff. Designed things and then handed them to engineers. Received designs and figured out how to build them. The friction everyone talks about — the Figma files that don't account for edge cases, the engineers who don't understand visual hierarchy — is real, but I don't think it's the actual problem.

For a long time I had a rule: don't talk about what you're building until it's done. Ship first, announce second. The thinking was that half-finished work says something unflattering about you.

Running a hackathon sounds straightforward until you're three days out and half your sponsors have gone quiet, the venue AV system is broken, and you have 200 people arriving on Saturday morning.