What is your worst financial horror story?

[Cue flashlight under the chin] I’m going to answer this question with a personal tale of woe.

When I was younger, I was reasonably financially responsible. I credit my parents with my money management skills. But then I decided to take a shit all over that. And, with a partner, opened a bar—the kind where people go to drink.

There were a lot of reasons not to pour my money into this bar. But I didn’t use any to say “no.” And that’s not only hindsight talking. I had doubts at the time. I suggested less complex alternatives. But it took me a long time before I started saying “no,” and by that time, I was deep in it.

It didn’t go well. I’ll spare you the details of undercapitalization, inexperienced owners, burnout, debt collectors, repossessions, and the rest. I was in a pit that I had to climb out of. And I did. It took me several years. And not without help – an attorney to renegotiate debt terms, a short-term loan at an attractive interest rate, and some luck/divine intervention.

The debts may be gone, but the regrets linger. I still sometimes think about the things I could have done with the money instead of flushing it down that toilet. And I want to blame my partner, but I can’t. No one put a gun to my head. It wasn’t blackmail. If I had said “no” in the beginning, it would have been a non-starter.

I really hope I’ve learned something from the experience. Mostly about listening to my gut, following common sense, and saying “no” when I want to say “no.” But sometimes I’m not that bright.


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