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5 Idiotic Money Mistakes From My 20’s

It sort of pains me to say that I’ll be turning 30 years old in May. It’s really hard to believe, but as I have been told by many that “time will only speed up.” So, I figured that instead of wallowing in my self-pity, I would attempt to be wise in my old(er) age and explore the blunders of my 20’s in an effort to avoid the same money mistakes in my 30’s. After much pondering and reminiscing, I have come up with five money mistakes that I have made in the past and absolutely NEVER want to make again.

money mistakes#1. Dragged My Feet on Investing

I started my professional career in September of 2008 when the market was near it’s all-time low. Sure, I didn’t make a ton of money starting out, and the company I worked for didn’t match my contribution, but these were just excuses so that I wouldn’t feel quite as bad about not investing for my future like I knew I was supposed to.

If I would have been wise, I would have looked for more work than my 40-hour per week temp job that paid just $16 an hour, because I could have then easily invested thousands into the market. Instead, I worked the bare minimum and played a TON of video games. To be completely honest, it was a pretty fun year, but by the end of it I still had no money and hadn’t yet put a dent into my student loans – a definite money mistake.

#2. Withdrew Money From My 401k

When I finally did get around to investing in my company 401k (because they started matching my contributions), I pulled another bonehead move. First of all, I ended up leaving the company to work elsewhere, and because I wasn’t vested in the company’s contribution until three years later, I ended up with none of that benefit. Secondly, instead of being wise and rolling that money into a new 401k with the next company, I decided to withdraw the entire amount and paid a 10% penalty because of it. Thankfully it wasn’t huge dollars, but it was still pretty stupid.

money mistakes volvo#3. Ignored Maintenance on My Volvo

Car maintenance can certainly be pesky and cost quite a few dollars here and there. When I lived down in Florida, my Volvo S80 seemed to be nickeling and diming me to death, so I made the wise move to just stop fixing stuff and hoped for the best (note the sarcasm). Instead of repairing a cracked coolant tank that would continually go dry (and cause my car to overheat) for $700, I ended up losing thousands because my head gasket eventually blew and made the car absolutely worthless. This decision to fix nothing probably cost me an extra $1,500 in the end, which definitely qualifies as an idiotic money mistake. If I would have just kept up with the maintenance, I probably could have driven that car for a couple more years.

#4. Spent Thousands Instead of Paying Down Debt

I was young, in debt, and in love, and on this rare occasion I let my emotions get the better of me. I was 23 years old and had recently moved to Florida because the job market in Michigan was absolutely terrible. Before moving, my Dad graciously loaned me $3,000 to buy a decent car (that Volvo that I was describing in money mistake #3), and had also agreed to sell my old car for me while I was away.

That old car didn’t sell very quickly (it definitely wasn’t anyone’s dream car), but when he did finally sell it, stupid me didn’t just give the money back to him. Nope. Instead, I ordered him to send me the cash so I could buy a wedding ring for my girlfriend. And, looking back, that probably wasn’t the best move since she left me four years later… Sorry, Dad.

#5. Missed a Huge Job Opportunity by Avoiding Confrontation

I don’t mean to pat myself on the back, but I am pretty quick when it comes to catching onto things and understanding complex situations, which makes me a pretty valuable employee. At the time, I was working at a company headquarters and was being offered a full-time job as a Merchandising Analyst. This sounds all well and good, but at the same time another department in the same company was interested in having me work for them as an e-Commerce Marketing Analyst. Before I really stopped to think about, the heads of the Merchandising department called me into their office and convinced me that there was much more room for growth with them, so I agreed and was immediately part of their team.

money mistakesAfter a couple weeks, I realized that their advice was total crap. I was now a Merchandising Analyst and my boss was a Senior Manager, who was three levels above me. What do you think the odds were of me moving up into that role? Pretty much zero. And, because the company was so siloed, I couldn’t move up into another department either. I was stuck.

If I would have taken the e-Commerce job, I would have likely been made into a manager in a year or less because it was such a booming department. My career could have taken off, but instead I was stuck in a thankless job with no chance of moving up or out into another department. This decision probably cost me hundreds of thousands of dollars over the course of my lifetime.

I Will Not Make These Same Mistakes Again

These five money mistakes were quite costly, and I fully intend to never make them again. Thankfully, there were many other potential mistakes that I have been able to avoid with the advice of other personal finance gurus via the net and quality books.

I advise you to learn from your financial mistakes as well. As you can see from my money mistakes above, I am not perfect. Nobody is. We have all made our fair share of money mistakes, so do not be ashamed of the poor choices of your past. Simply learning from your mistakes could make the difference between a wealthy future and a mediocre, paycheck-to-paycheck lifestyle. Choose the path to wealth and freedom and dare to learn from your past mistakes.

What money mistakes have you made in the past?

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My name is Derek, and I have my Bachelors Degree in Finance from Grand Valley State University. After graduation, I was not able to find a job that fully utilized my degree, but I still had a passion for Finance! So, I decided to focus my passion in the stock market. I studied Cash Flows, Balance Sheets, and Income Statements, put some money into the market and saw a good return on my investment. As satisfying as this was, I still felt that something was missing. I have a passion for Finance, but I also have a passion for people. If you have a willingness to learn, I will continue to teach.


  1. Oh man,a comment box is not big enough for mine! I do like the saying “Live and Learn”. It’s awesome though that you realized things before 30. I have been so low and beyond stupid with money that I am actually in a good place right now despite my debt. That is my positive 🙂 I would say yours is you made mistakes young and learned from them young so you got time.

    • Sounds like you’re already in the process of taking that “hard left” to turn your finances around, Dawn. Good for you!

  2. These are definitely mistakes but nothing that will derail you from your goals and your opportunities in the long run. I’ve made similar mistakes and the key is to learn from them and don’t repeat the same mistake more than once. Do that and you’ll be fine!

    • True. Since I had a solid overall focus from a young age, I didn’t get derailed to badly. Compared to most, I am in a great spot right now. Thanks for the comment MB!

  3. We definitely all make mistakes, but it is important that you have learned from those mistakes! I’ve also made some mistakes, and I have definitely learned from them as well. Thanks for sharing!

    • Thanks for leaving your comments Lauren! Learning from our mistakes sounds easy, but many of us don’t even realize when we’ve made them! This is where education and reflection are important.

  4. I made the same mistake by ignoring maintenance with my Chevy Malibu. The head gasket also blew as well. I know I will never make that mistake again.

    • Yeah, ditto. That moment when you know your car has become completely worthless is nothing I want to experience again! 😉

  5. The best lesson learned is that those were mistakes and how to make better decisions the next time. There are some people that wouldn’t have realized they were mistakes and they will continue to make mistake after mistake.

    • True. There are PLENTY of people that never realize their mistakes. But, it still sucks to make them in the first place, whether you realize it or not…

  6. Those are pretty big mistakes, but you have come a long way! It just shows you that no matter how much we screw up, we can make up for it by making smarter choices going forward. The key though is to make a change and not just stay on the same path.

    • There is always room for learning and improvement, no matter who you are! Thanks for the comment, Jon.

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