I have two. I wish I had finished my college degree when I was young, unmarried, and working part time instead of cramming 4 years into 24. That’s right; 24 years separated my first college course (an 8am English class in the fall of 1984) from my last (a senior project in May 2008). By the time I finished, I was paying more for a textbook than I started out paying for a class. I’m glad I finished (my fiancée likely would never have even spoken to me if I hadn’t had a degree), but I finished with a load of student loans I wouldn’t have had if I had done it the right way. And my career might have advanced farther faster if my resume had gotten put in the stack to be interviewed instead of rejected without examination because I didn’t have a degree.
Second, I wish I had done at least one tour of some sort of military service. It would have been the perfect time. It was after Vietnam but before Desert Storm. The biggest thing we invaded was the island of Grenada, which I think required a bass boat, four riflemen and a squad of cooks. But alas, I had already discovered the allure of making just enough money to spend it all, and the military don’t pay SQUAT (a fact I will rectify one day when I’m President).