Like others I have mentally ill relatives recklessly blowing through their money.
However, I also have friends who lived below their means for years, followed the advice of bankers and financial advisers, and ended up with huge financial losses in 2008 and beyond. One friend had bought her modest house for cash, but lost all the money that was supposed to pay for her kids’ college and had to mortgage the house since there was no market to sell it anymore, and so on… … I really can’t see where she went wrong except she followed the advice of a paid expert. I think she lost more than a million dollars. She did everything the expert told her, including finally divesting herself of some things probably at the exact wrong time… when she really didn’t seem to me to have anything left to lose, but I don’t pretend to understand what all went on. I know before she hired him she had at least a million in cash (insurance and inheritance) that she felt was too much money not to invest. She will not be retiring at 65.
adding: I know more than one person taken advantage of during those years, some worse than others. I just still can’t believe anyone would knowingly take advantage of a widow with children. fwiw

Totally get it. We drive our vehicles into the ground too.