Financial Blunders So Thoughtless, It’s Scary!

MichaelBeliefs, Education, Misc, Real Estate, Saving Money, Taxes16 Comments

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Happy Halloween friends!  I hope you’re enjoying this fun holiday with some good company.

In the spirit of this spooky holiday, I thought it’d be fun to recount a few of my financial blunders.  Some are so thoughtless, it’s SCARY!!

Hopefully, you can learn from my money mistakes, or at least have a quick laugh.

1. Stole $40 from My Dad’s Wallet

financial blundersSo when I was just 8 years old, I really wanted to get my hands on some cold hard cash!  My juvenile desire was so great that I stole two $20 bills from my Dad’s wallet and denied ever seeing them when he came asking us kids if we’d seen it.  A month or two passed and I had to launder it.

So, I took one of the $20 bills with me one day when we were shopping in a bookstore.  In an empty aisle I dropped the $20 bill, then walked around a minute before returning.  When my sister and Mom were in view, I did my best acting, “Oh my gosh!!  I just found $20!”  After a couple high fives, I pocketed it and returned it home into my piggy bank.

To be honest, I don’t know what I did with the other twenty, but my Dad never officially called me out even if he had his suspicions.  Instead, he taught me the value of money over the years by example.  Thanks, Dad!

2. Destroyed a Rare Baseball Card

baseball-cardIn elementary school, I coerced my friend into trading me a pretty expensive baseball card (worth $750 today) for several other cards that were essentially worthless… yes, I know… that wasn’t very nice!!

To make matters worse, I carried the rare baseball card out during recess in my pocket.  After playing 20 minutes of dodgeball, the near-mint baseball card had a two new creases right down the middle of it.  This essentially cut the value of the card by 95%… ouch!

Perhaps it was a bit of poetic justice since I wasn’t too nice to begin with.

3. Bought a Rental Home That Couldn’t Be Rented

RH2After the last housing downturn in 2008, I finally pulled the trigger and purchased my very first rental home.  I was elated because the numbers looked great in my pro forma (estimated projections).  I was super proud of myself for waiting until the market corrected itself in 2010.

There was only one problem.  I couldn’t rent it out!  Turns out there was a long-term (99 year) rental restriction on the property.  I was s&$! out of luck.  If you’d like to read more about how it all worked out, check out my post – My First Rental Property Was a FAT Failure.

Make sure you read EVERYTHING before you sign your contract.

4. Worked One Day for a Year

stupid-487043_640I had been looking for a job during the summer leading into my senior year of high school.  Nothing really caught my attention until my cousin gave me a referral to work the concessions stand at the Hollywood Bowl.  I excitedly jumped on the opportunity and drove over later that week for a quick interview.  They said okay and I scheduled my first evening.

The following week I worked one evening for 5 hours and got paid $4/hour.  I made a whopping $20!  I never returned after that one night because I started back to school the week after.  Additionally, it also took me over an hour to commute to the location, so I also wasted gas and time getting there and back.

Here’s what else was lame.  I was set up as a W2 employee so I had taxes withheld on $20.  I wasn’t about to file a tax return on $20 of income that year, so I blindly gave Uncle Sam my money for free.  Ahhh, to be young and ignorant.

5. Wasted $300 on a Horse Betting System

horse-racingAs a kid, I was always fascinated by gambling.  Trips to Las Vegas gave me googly eyes and my ears focused in the clanging of falling quarters.

My cousin and I realized that we could legally gamble when we turned 18… at least at the race track.

As soon as I turned 18, my best friend and I made a trip to the local horse racing track.  We were super psych’d up to go because we had just purchased a brand new $150 horse betting system that was a sure thing!

It turned out the systems didn’t work at all and we lost another couple hundred dollars in bets that day.

A couple of years later in a college statistics class, I finally studied the expected odds of gambling.  I was crushed to find out that the odds were rigged against me from the beginning.  Gambling completely lost it’s prior allure and it’s one of my least favorite past times.

6. Paid a Fake Border Crossing Fee

stopI don’t know about you, but sometimes when you’re traveling in a foreign country (especially a 3rd world country), it can get a bit stressful trying to comply with pertinent laws, taxes, and fees.

My wife and I were traveling in Central America with some friends and decided to take a quick side tour into Guatemala from Belize.  When we got to the border there were signs clearly marked NO FEE to exit or enter Guatemala.

When we entered, we were greeted by uniformed officials asking us to pay an entrance tax.  We were a bit suspicious of this tax, but with limited Spanish we ultimately complied.  It came out to $20 for the 4 of us.  It wasn’t a lot of money, but when you’re under stress you don’t think as well.  We gave them the money and moved on.

I hate getting scammed!!


Sometimes the most thoughtless mistakes we make with money are also the most valuable ones.

You can see when I was young, I made some poor judgment calls because I thought I wanted money.  When I was older, I still made mistakes, but it was at least with the right intentions.

One thing to observe is how your financial mistakes mature over time.  Which ones are the scariest to you?

Readers, what are some of your most thoughtless financial blunders of all time?  What did you learn from them?


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Hi, I have been blessed to take an early retirement in my mid-30's so I can focus on becoming a better father, blogger, and investor.

My goal is to help you find your personal path to financial freedom, and to enjoy the entire journey.

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16 Comments on “Financial Blunders So Thoughtless, It’s Scary!”

  1. These are some great stories Michael. On the last one, if a uniformed officer is asking for $20, it’s kind of hard to say no. I’d categorize that as more in the “getting robbed” category than making a bad final decision.

  2. Rather than call these ‘mistakes’, you could think of these as lessons learned…because that’s what they really are!

    Without making mistakes, we can’t learn! I bet you’ll never need to repeat any of these ‘lessons’ again!

    1. Agreed, Mr. Tako… but ‘lessons learned’ doesn’t sound as sexy! 😉

      And don’t be so sure I won’t repeat these same ‘lessons’ again…hah.

  3. I can’t believe you couldn’t rent out your own home because of a clause in the contract. Former owners shouldn’t be able to control what you do when it’s your own property!

    There are great stories Michael, thank you for sharing them 🙂

    1. Well, it wasn’t the former owner, FS. It was the homeowners association that the property was a part of. Either way, it sucked and I was picking myself in the pants for many years!

  4. That’s hilarious. I have many similar stories.

    I was really into baseball cards when I was young – what was the card you traded for?

    Super into gambling too – when I turned 18 my friends and I drove nearly 2 hours to the Chumash Indian Casino pretty regularly haha.

    Then when I was 19 I have a pretty similar story of not working. After my first year in college I was living at home and my parents said I needed to get a summer job. So I interviewed at Jamba Juice and was offered the job. I figured that satisfied the requirement and I didn’t ever follow up to schedule getting started ….

    1. Brian, the card that got smashed as a Topps 1968 Johnny Bench Rookie card.

      That’s so funny you have so many of the same stories. What was your game of choice at the Indian casino?

  5. Those are some good ones, Michael. Hope you had a fun Halloween.

    I love the story about the mint condition baseball card…that’s a shame it was ruined! My brothers and I collected all sorts of cards for years and years and had some good ones. After we were grown and moved out, they were stored safely in books and plastic coverings to keep them in good shape…all held in my parents closet. They moved houses and without knowing it until after that they got rid of all the cards! Bummer!

  6. I think my biggest financial mistakes would be spending every dollar I earned in college on idiotic brand name clothes. I bought tons of Lacoste polos that I would never even wear today. Truly a waste of cash!

    1. Yes! Don’t you hate it when you spend a bunch of money on stuff you ultimately don’t use. I don’t know about you, but when I do that I tend to just keep it so I don’t feel like I’ve completely wasted it. But, sometimes that’s even worse!

      I don’t think I’ve worm a Lacoste polo since elementary school. 😉

  7. Cheers for sharing Mike and I particularly like the border crossing one ;)!
    Glad you learned from taking $40 from your day as well..

    I’d have to say mine is “investing” 5K into a FX trading system that was supposed to be simple and require 20 mins per day..

    What you realise from this is the importance of doing your due diligence and that usually it’s not as easy as it’s presented..

    Hope you’re well man!

      1. The 5K I spent was for the training, I didn’t actually end up placing any live FX trades. it was a relatively high pressure sell at a seminar for a company.. They did provide support and on-going education although it was much more involved then originally suggested..

        Definitely a powerful lesson learned 🙂

  8. Those are some tough lessons. But in the end the wisdom gained is a lot more valuable than what you lost at the time. The border crossing fee was interesting. I can’t imagine what other types of scams they have ready for tourists.

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