Dumbest things I have ever done. Let me think...
1) Buying our first house in 1973, we wanted to be home owners before we understood what that actually meant.
2) Buying a 1974 Fiat.
3) Buying a beat-up VW van around 1978.
4) Buying a beat-up VW Beetle around 1980.
5) Buying our second house in 1982 @ a 9% mortgage rate.
6) Buying our third house in 1987 @ a 13% mortgage rate.
7) Working for a company that had no ethical compass.