I could write a long list, but I got to FIRE eventually, so fuck it. It all worked out fine in the end. My five-year FIREversary is next week.
I wrote myself a list at one point, to confront my regrets and get over them. This might seem like strange behavior from a post-FIRE perspective, but there's a certain bitterness you have to choke back when you're facing a 7 year sentence in cubicle prison and you know your own boneheaded choices put you there. Mine included things like:
-picking a low-pay college major
-prioritizing the purchase of a house
-trading up to a bigger house
-driving a truck for years
-buying a fixer-upper investment property and pouring my energy into it instead of getting a master's degree 5 years earlier than I did. (I earned minimum wage or less on that adventure)
-buying high-dividend stocks instead of growth stocks
-buying a boat
-sticking with a relatively conservative stock allocation from 2009-2015 (cost estimate: $250k).
-I once bet, and lost, $5k on gold puts before I understood much about how options worked.
-I sold an AMZN $1,000 strike call option last summer because I was down 25% on a $5k investment (trying to avoid my earlier mistake with gold). Had I held I would have quadrupled my money.
-I was sitting in a master's-level economics classroom in late 2008, learning about monetary velocity and how the great depression occurred, realizing that the government was doing all the correct things to avoid a depression right at that moment, and STILL failed to go all-in and stay all-in in the midst of the SECOND crash of my investing career.
The net value of these mistakes? Probably millions. Yet, the satisfying part - maybe only to me - is knowing the following: You had to learn these lessons, you'll never make those specific mistakes again, and the universe of mistakes you are vulnerable to has shrunken by that many. Learning and chicken pox are a lot alike.
It wasn't all a self-beatdown. I also wrote a contrasting list of things that I did well, especially if I went against trends to do so. E.g. maintaining full-ride scholarship at a state school, doing my own house and auto repairs, always earning the 401k match even when my pay sucked, marrying a relatively high earner who's also frugal, etc. The exercise was worth it.