28 years ago...Selling my house in Ojai, CA at the bottom of a R.E. cycle and getting locked out of home ownership for many years as the price of homes went up, up ,up...... I Squandered the profit on cars, boats & crap. (I was 23 years old) & paid capital gains taxes.

Playing the rigged options market.

Using credit cards to 'help' bridge cash flow in a small business and then not paying the cards off right away.

And Any debt.
Maybe these are the best financial lessons that ever happened to me....I learned my lesson.

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"Our Lady of Blessed Acceleration...
don't Fail Us Now"