Multiple times, because I'm boneheaded
Showed up to an Air Force Academy interview in high school and didn't think to wear a suit jacket, depsite my father telling me to wear the damn jacket. Walked into the room where the other candidates were, and everyone else was fully suited up. The fukking embarrassment...
Failed almost all my courses or got D's my first semester in college trying to live The American Pie life.
Flunked my pilot's license exam and had to shell out another 500 dollars a month later, instead of being proactive with my studies.
Got fired from my first job out of college for not doing the bare minimum.
I'd say recently again, as lifestyle creep was starting to affect my finances as of late. Nothing devastating, but I live in Cali, and I'm looking to secure home ownership and a new car in the next few years, so I gotta tighten my belt build my wealth up instead of falling pretty to consumerism ploys meant to divorce people from their money.