What are the Biggest Financial Mistakes You’ve Made?

I’ve come a long way in my financial journey. From a debt-ridden college grad who struggled to pay her bills to a homeowner who’s financially stable enough to start her own business, it’s been quite a ride.

Learn from your financial mistakes Big Money Mistakes

Along the way, I’ve had my fair share of mistakes (and then some!). But I wouldn’t change too many things. Sure, if I hadn’t made these mistakes I’d most likely have a lot more money now, but I’ve always said that I’m happy because if I had to make financial mistakes, thank goodness I did so at a young age.

In making these mistakes over the years, I’ve learned so much about myself, about money and about the psychology behind financial decisions. I’ve also learned how to budget, why it’s important to save for retirement and how to gain control over emotional spending.

With each mistake I make, I take time to analyze my mishaps to the best of my ability. I try to figure out the who, what, when, where and why in an effort to avoid making the same mistake(s) in the future. After all, if you’re not learning from your mistakes and aren’t changing your behaviors, what’s the point in analyzing anything?

Big financial mistakes I’ve made

If I were to list all of the mistakes I’ve made with money over the years, I’m quite certain this list would be way too long. Instead, I’ll focus on the biggest ones that have had the largest impact on my financial present and future:

I put my head in the sand

When I was struggling with ballooning credit card balances, I made a horrible error by trying to ignore the situation. Despite how I joke about becoming the Princess of Interest and Queen of the Shredder, I shudder to think about how I used to behave. If only I’d faced the situation head-on earlier, I’d probably have saved myself thousands by not spending mindless and recklessly.

I shopped away stress

Accumulating all of my past credit card debt (Yep, over $14K) didn’t happen overnight. It was a product of my misaligned tendency to shop when I was stressed, angry, bored or wanting to feel social. I viewed shopping as an outlet rather than a necessity for finding the things I need at a great price. I was all about the want when I really should have focused on the need. I also, for a brief period of time, defined myself and self worth by the things I had and the money I could spend…ugh…ick…blech.

I struggled in silence

Not once did I reach out to family or friends about my financial situation. Why? Because deep down, I was ashamed, embarrassed and felt guilty. Instead of asking for help or soliciting advice from those I trusted, I continued to shop my way into oblivion. It wasn’t until I discovered the MSN Money boards that I found some much-needed inspiration and support to tackle my financial demons.


What are the biggest financial mistakes you’ve made?


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Freelancer; reformed spendaholic; risk taker; adventure seeker; world traveler; rose smeller; debt destroyer. My mission is to inspire others to live a healthy, balanced life one cent at a time.


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  1. The biggest mistake I made was loaning money to someone I was only dating. Needless to say, we broke up and she refused to pay back the $5k. Its ironic because I ended the relationship after realizing she wasn't the kind of person that would honor her debts. I knew the money was gone, but it was worth it.

    • I lucked out with my purchase, even though my first-floor neighbor was a nightmare for a while. I advocate that people visit their potential neighbors and the area at least four different times (weekday, weeknight, weekend day, weekend night). A little research goes a long way!

      Sorry you had to go through that though–I know how stressful it can be!

  2. I've never made any credit card blunders but my big mistake is co signing on a student loan for my then husband. It's a tough spot to be in. He begged me to and I wasn't comfortable with it but didn't feel I had a choice. Since being divorced it's that one thing hanging over my head. BOO!! Oh well. Such is life.
    My recent post Four Day Weekend

  3. Our biggest financial mistake was actually not SPENDING some money! When my husband was in school, we put every penny into paying his tuition. We didn't date, didn't travel, didn't spend any money on ourselves. And by the end of six years (yep, that's how long it took him to finally finish school), we were walking on a dangerous edge in our relationships. We since became a lot closer again. But I wish we would invest a little more money in us and nourish our marriage. No matter why you try to save money (paying debt, invest etc. etc.), never forget about things in life that are a lot more important than a bank account.
    My recent post Our half bath reveal!

  4. Does it have to be just one financial mistake?! ;) I think for me it was funding several vacations entirely with credit cards. Sure, it they were fun when they lasted but I spent years paying those needless vacations off.

  5. Well, prior to getting into rental property for ourselves, my wife and I put at least $150k into a series of debt and equity deals with a struggling company. While it's still possible that the money could come back (and it's even possible it could become hugely profitable), it is also possible that it will be a total loss. Fortunately, we're still in our 20's and doing very well financially, so we'll chalk it up to a tuition payment to the school of investing!

      • Not likely, except for the education as I mentioned…But we've made a number of much better investments since which produce monthly cash flow, and we'll consider any return we might receive from the previous investments to be gravy (which would be reinvested). Thanks though!

        • You're welcome–I'm a hopeless optimist when it comes to things eventually working themselves out. But you're right, the education aspect of a situation like this is huge.

          Good to hear that your other investments are working out better—cash is king!

  6. I will have to say getting married before finishing school. I thought I could still get Pell grants and continue with school. I was advised by many people in my life that it was the best choice for the time, but I wish one person would have known about school. At the time none of the people in my life cared if I was in school, but I dropped them all to the curb not too long after that. I am glad for the mistake, because I learned a lot about finances since then. I also learned that two people making $8.50 an hour is considered livable wages and the government won't help in the slightest…
    My recent post What is your Daily Survival Number?

    • Wow…that's unreal about the livable wages bit…how on Earth?

      I'm sorry you had to go through such an ordeal with school and with those people–I hope everything has worked out for the best! You can never discount a learning experience in my opinion

  7. The biggest mistake I made was not starting and following a budget when I became a freelancer when I was laid off. I had such a huge cushion to work with and I blew it because I was careless. In my (sort of) defense I wasn't prepared at all to become a freelancer because of the circumstances, which is what I hope to teach through my blog.
    My recent post Are you living a life using all of your 5 senses?

  8. I ran up credit cards several times and I once bought a $25,000 car without having a job at the time! Thankfully, I learned from all of my mistakes and quit repeating them.

  9. When I was 22 I was driving a fairly new Toyota Tundra, which had a big payment and was very inefficient on gas. I made a decision to sell it and buy a cheap used car that was more fuel efficient. Three days later I walked off of a car lot with a brand new, $21,000 Mitsubishi Lancer. :)

  10. I have made a few financial mistakes in my life but the biggest thing I regret is not educating myself on finances until later in life. In hindsight I should have started earlier. My parents didn't teach the value of your finances. My mother had terrible spending habits she has declared bankruptcy twice so I had to learn all this stuff on my own.
    My recent post Yale and Harvard Suing Their Student for Default

    • I'm writing about the impact parents have on the future decisions their children make about finances—please come back and visit :)

      But it's so true…it's never too early to learn about money and how to use it well!

  11. I have a couple…

    1st – not filing charges against a my x-husbands sister when she stole my SS# and got some credit cards in my name. Wrote some checks on my checking account (x husband begged me not to press charges because it was his sister….)

    2nd – Staying in the above relationship far to long wasting my time being put behind "but they are my family"

    3rd – after finally leaving the above relationship and filing for divorce, I walked away with a nice hunk of money that I put in a money market account and moved home for a bit trying to decide what or where I was going live. My dad kept telling I should buy a place. I really just wanted to rent a nice little apartment or share a house with a friend. Only to succumb to dads wisdom of buying something. I bought a condo…it offered me the apartment living but at a huge cost.

    I've been here 8 years. My property values have dumped with everyone forcloseing or short selling that my 2005 purchase of 195k was 224k in 2008 and is now 106K….still owing 137k on it. Zillow says $169K but the comps aren't there. We could rent it for 1200 to 1250…which is about the cost of the mortgage and condo fee, which includes heat and cooking. But do we (I did get remarried) really want to become landlords….sigh.

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