Many times in my life I have continued doing something, even though I knew it was the wrong thing (or the stupid thing to do) just because I couldn’t figure out how to end things. You may recollect some of my bigger screw ups from My Top 5 Investing Regrets in my Life, but there are plenty of others out there as well.
You say you’d like examples of these humiliations in my life? I am nothing if not accommodating:
- Continuing to pay for whole life insurance long after I had figured out I was paying too much for something I didn’t need at the time (I was 24 at the time). Why didn’t I just walk away sooner? Stupidity is as good a guess as any.
- Had a mortgage at 12% annual rate and didn’t go in to renegotiate when rates had gone down to 6% and I had a year still left!
- Held onto Nortel shares for far too long, and got badly burned by it’s eventual demise. I’d like to say I did the same with stock options, but my options were never worth any more than $326.51 (which I never saw).
- Didn’t get out of TD Mutual funds in my kids’ RESP accounts, in fact I should have transferred it all over to TD Waterhouse, now I didn’t really lose money on the deal, but it does still beg the question, “What was I thinking?”
- Left money on my credit cards and paid the outrageous credit card interest rates for about 2 years, again, “What was I thinking?”
The Ultimate Example
This photo shows the ultimate example of someone who should have just stopped and waited for a tow truck. If you look closely you see a missing right rear tire and an imprint in the parking lot where the driver pulled it into this parking spot. I took this photo a while ago, but it sticks with me as a good example of, what were you thinking?

Was it Worth It?
“I just figured I’d drive and find a spot to park the car”, that is the only thing that I can guess the driver was thinking



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