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It was some time in the 2000s, and I was at the outlets in Flemington, New Jersey. I stumbled upon a pair of black leather Cole Haan shoes priced at $75, marked down from $300. It was the only pair left, and the shoes happened to be my size. How could I possibly resist?
I hated those shoes. No matter how many times I wore the darned things—and, trust me, I didn’t give up easily—my feet screamed. The stiff leather never got any softer, and the shoes ended up languishing at the back of my closet for years until I finally stuffed them in the charity bin at the local supermarket.
The lesson: Just because something is on sale doesn’t mean it’s a bargain.
So, what purchase do you most regret?
I don’t really regret my purchases. I was thoughtful when I made them and I’ve really learned from them, even the bad ones. That was all a part of life.
(Like what a sunk cost? That would be funny except for the fact my wife and I were once led to invest in a small submarine for tourists to see underwater fish, rays and other wildlife. It was a fun operating business in Hawaii that wanted to expand to the Virgin Islands. And we were young and impressionable. It was a limited partnership investment in the very low five figures. Now THAT was a “sunk” cost. It went bad, but we actually got more than 50% of our money back in the end, so I’m not ashamed to tell the story.)
But I do greatly regret not exercising options and diversifying a big chunk of my portfolio when the company I worked for was sold. I later took a big hit when the new managers stumbled, and that was on me. That was a “non-purchase”. Cie la vie.
It was the late 70’s and runaway inflation. I was snookered into buying – of all things – “investment grade” collectible tax stamps. Based on the sincerity of the stamp broker and his evidence of the stamp’s rapid growth in value, it was certain to be a sweet deal… until it turned sour. Once I became disenchanted with the speculative returns, it quickly became apparent that I didn’t have a clue what I was investing in, and that I failed to consider ease of liquidation and transaction fees.
The loss on that sure-thing-investment still smarts. But, it taught me to be a whole lot more Humble with my Dollar!
My sister was going to make a killing collecting Beenie Babies.
Something I’ve heard people commonly purchase and then regret is expensive exercise equipment. We’ve bought several that we’ve gotten great use out of, but the one I’m thinking of was used a few times and never again. We ended up selling it back to the store as used for a lot less.
Worst by far was shorting orange juice futures a week before a significant snap freeze in Florida in the early 80s. Couldn’t get out for 5 sleepless nights!