Lesson #1 - play a lot with better players. I am fortunate to play fairly often with some top pro's; it makes the run of the mill good players a lot less imposing.
Lesson #2 - I haven't found my choke point yet, in terms of dollars. I no longer get nervous in league play, even near the end of a long, close match. I no longer get nervous in local 9-ball tournament play. I still get NERVOUS AS HELL playing with a top touring pro, even though I consider them a friend - it's stupid and I need to get over it.
Lesson #3 - there's no need to avoid playing someone you don't know, just step up, have a little heart, but don't let it hurt you financially. If this guy would have been older I probably would not have played for that much - thinking he probably was OHB in disguise.
Lesson #4 - Money won is just the same as money earned - I got no great thrill from it - probably would have been just as pleased if we were playing for fun, it's cool being able to compete with good players. I'm not sure how I would have felt if I lost, probably bad, probably won't wager this much in the future.