This isn't the stupidist financial "mistake" but it is worth noting.
A few years ago I was eyeing a stock that had gotten beaten down hard during the market crash in 2008. I could've gotten in around $2 a share. I decided to wait. Two weeks later the stock jumped to $15 a share. I could've turned $2000 into $15000 in two weeks. I still kick myself over that one.
A few years ago I was eyeing a stock that had gotten beaten down hard during the market crash in 2008. I could've gotten in around $2 a share. I decided to wait. Two weeks later the stock jumped to $15 a share. I could've turned $2000 into $15000 in two weeks. I still kick myself over that one.

The market was red hot, homes sold in 5 minutes (As they had for decades), and not even our really fiscally conservative relatives thought twice about our plan our cautioned us. But 9/11 happened and we lost $100,000 over night. {To be fair - with the last bubble burst, it was much slower in coming - and far more predictable, if you ask me. People weren't losing $100,000 in "one day" just out of nowhere}. BUT, we were buying the second home very conservatively, and had lots of options, so just went through with it. I can't say I would change anything (except selling house #1 sooner if I had a crystal ball). But I do admit next time I would ask myself, "How would I feel if house #1 plummeted in value overnight?" It's kind of a catch 22, because I have seen real estate skyrocket here overnight too. (& if we abandoned our planned and bought any later, we might have had to pay $100+ more on new home - which is largely why we just went through with home #2 purchase). So, I can't say I learned to "never buy a new house without selling the old one." I have just learned that nothing is certain - don't count your eggs before they hatch - *anything* can happen!
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