My 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 everyday money leaks or niggling oversights we all make from time to time, like leaving the lights on or buying a burger at a fast food joint and then forgetting to use the 2-for-1 coupon in your wallet.

Instead, I want to address the type of money mistakes that continue to haunt me. Epic bloopers that still wake me up and leave me covered in a cold sweat.

Here, in reverse order, are ten of the dumbest. True, some of these slipups aren’t expensive, but they all could have been avoided.

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. In 1997 I saved over $1000 getting the backyard of my new house landscaped. One contractor presented an estimate that was significantly lower than the next highest bid, but I didn’t question him. After all, I was ecstatic that he was willing to give me such a great deal! Unfortunately, I eventually discovered how he was able to give me such a “great” deal; in fact, for the next several years I was reminded every time a shoddy pipe, valve or sprinkler head that was used to cut corners failed.

9. The hope chest I bought for an old 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. The 7-day 6-night vacation in the Bahamas.

If somebody offers you a Christmas present that happens to be a 7-day, 6-night “package deal” to the Bahamas for two for $199, it’s probably not a good deal. Although this was back in 1991, if you take inflation into account that still amounts to a little more than $300 today. My girlfriend and I took the bait and it ended up being the worst vacation ever. It turns out that “all-inclusive” did not include: 1) our airfare from Los Angeles to Miami; 2) food; 3) drinks; 4) entertainment. It did cover lodging in a dilapidated apartment in a terrible part of town, and a five-hour “cruise” from Miami to the Bahamas — in a rusty old boat that looked like it should have been towing barges up and down the Mississippi River. Adding insult to injury, it never stopped raining. Anyway, on day four we cut our “all-inclusive vacation” short and returned home. The Bahamas suck.

7. Buying Styx’ Kilroy Was Here album.

In 1981, Styx released their epic album Paradise Theatre. I would pop that compact cassette in my little 1971 Datsun 510 and play it so many times that I eventually wore it out. 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. Big mistake. The album was a complete and utter abomination. I really should have known — after all, the first single from the album was something called “Mr. Roboto.” Domo arigato. From what I can tell, that means “buyer beware” in Japanese.

6. Investing $1000 in a recording studio.

Speaking of music, I spent five years of my youth in a rock and roll band. We were known as the Relics and we even made an album (that went nowhere, but got this cool review many years later). At some point during 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 his home recording studio in exchange for free recording time. Heck, I even contributed a couple hundred hours of labor on the project. The bottom line: Once the guy got his studio finished, he was finished with us too. We never saw him again.

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

Photo Credit: Pic 2 Fly


  1. 13


    Ouch, some of them kinda hurt 😉

    My biggest mistake was not saving money when I was younger and getting into debt for car I could have saved for.

  2. 15


    Heh heh, that’s hilarious. Sorry about your all inclusive vacation. :)
    I got the cheapest mouse from office depot a couple of months ago and it broke already. That’s the last one I remember. Next time, I’ll get the 2nd cheapest one. Jeez…

  3. 17


    We all make dumb mistakes with money. We wouldn’t be human if we were all money geniuses from birth. What a bummer that you had such an awful vacation experience. That’s the worst. Can’t wait to read part two.

  4. 18


    I have had the same type of experience you had with the recording studio. I started a web design business with my friend and a guy who owned a local bar. Our first client paid us $3000 for a great website I spent weeks perfecting. Once the money came in the bar owner decided we needed to buy a special computer for upcoming projects. Suddenly once the computer was bought the bar guy decided he didn’t want to participate anymore and took off with the computer. (now that I am smarted I realize how important a lawyer, contracts, and getting everything in writing is) I never saw a dime of the money and our business struggled to pay our bills without that much needed money. It was a mistake I will never make again!


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