Nobody’s Perfect: My 10 Dumbest Money Mistakes

Money mistakes. We’ve all made them during our lives at one time or another.

Today I’m not going to talk about the little mistakes we make on occasion, like going to the movies on a whim and finding out if you had gotten there 30 minutes earlier you could have taken advantage of the 50%-off matinee prices.

Or betting your buddy from Boston $100 that the Lakers would beat the Celtics in the 2008 NBA Finals, even without Andrew Bynum and Trevor Ariza — although that was painful.

Instead, I’m going to talk about the type of money mistakes that really haunt some people — and by that I mean the truly stupid stuff that occasionally gives folks nightmares and leaves them waking up in a cold sweat.

I know I’ve made at least ten of them over my lifetime.

So, as a public service to you, my loyal readers, I now share with you in reverse order, ten of the dumbest money moves I’ve ever made. Some items are not expensive mistakes, but they are all very dumb mistakes that could have been avoided.

In any case, always remember: Do as I say, not as I do…

10. Trying to save a few bucks on my lawn and irrigation contractor.

When evaluating multiple contractor bids for anything, the lowest price is not necessarily the best deal — especially if the lowest price is significantly less than the other offers. In 1997 I saved over $1000 getting the backyard of my new house landscaped. Curiously, the quoted price from the contractor I selected was significantly lower than the next highest bid, but that didn’t deter me at all, no sir. Instead of questioning how he could offer such a ridiculously low price, I was simply ecstatic that the contractor would give me such a great deal! Twelve years later I continue to be reminded on an annual basis exactly how he was able to give me such a “great” deal, the answer revealed every time a sprinkler pipe bursts due to the shoddy material the contractor used to cut corners.

9. The hope chest I bought for my girlfriend.

Note to self: Never buy your girlfriend or wife an expensive birthday present if you have any inkling that she is going to dump you one month later.

8. Buying Styx’s Kilroy Was Here album.

In 1981, Styx released their epic album Paradise Theatre. I played it so many times in my little Datsun 510 that I ended up wearing the first cassette out, which required me to trudge back to Tower Records and buy another one. (Kids, if you aren’t sure what a record or cassette tape is, drop me a comment and Uncle Len will tell you all about it.) Needless to say, when Styx finally released their follow-up album, Kilroy Was Here, I was the first one in line at Tower Records to buy it. Little did I know that the album was a complete abomination, but I have nobody to blame but myself. I really should have known better; after all, the first single from the album was Mr. Roboto. And, yes, I realize it was only $8, but that album was really bad.

7. The 7-day 6-night “all-inclusive package-deal” vacation in the Bahamas.

Note to Self #2: If somebody offers you a Christmas present that happens to be a 7-day, 6-night “package deal” to the Bahamas for two for $235.99, it’s probably not a good deal. I don’t care if the year was 1991; taking inflation into account that still amounts to only $355 in current-year dollars. By the way, it turned out that “all-inclusive” did not include: 1) our airfare from Los Angeles to Miami; 2) food; 3) drinks; 4) entertainment. What it did cover was lodging in a dilapidated apartment pretending to be a “luxury condo,” and a 5-hour “cruise” from Miami to the Bahamas in a rusty old boat that looked better-suited to towing barges up the Mississippi River. To top it all off, the first three days we were there it never stopped raining. We eventually decided to cut our “all-inclusive vacation” short and returned home on day four. The sun finally broke out from the clouds on our “return cruise” to Miami. The Bahamas suck.

6. “Investing” $1000 in a recording studio.

For five years, I was in a rock and roll band. We were known as the Relics and we even made an album I am very proud of (more on this in Part 2). Early on in my misguided quest to become a rock and roll star, our band was befriended by a smooth-talking shyster who actually got me to “invest” $1000 of my hard-earned money into the construction of a recording studio that was to be located in this guy’s house. In return, the band would be allowed to record our album for free. Heck, I even contributed a couple hundred hours of labor on the project. Bottom line: once the guy got his studio finished, he was pretty much finished with us too. Yes, that wrapper around my head does indeed say “Tootsie Pop.”

The first five mistakes listed here are minor and relatively inexpensive. I discuss the remaining five dumbest money mistakes I ever made in Part 2 of this article — and, I promise you, they are not only dumb, but really expensive too.

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