Jan. 9, 2021

My All-Time Greatest Money Mistakes

Success Through Failure

It is never easy to admit a mistake. It is tough to talk to about money mistakes. Like religion and politics, money is one of those taboo subjects that people do not like to speak openly about. Throughout most of my adult life, I was just like everyone else in that regard. From the outside in, I am sure that I looked like I had my money life together. In many ways, I did. But in more ways, I was a mess.

As my wife and I are now approaching financial independence and retirement, I have decided to take a fun look back and the mistakes we have made along the way. I consider these mistakes “great” because we could learn from them and come out the other side. Mistakes are impermanent. You have to “start where you are.” Scott Adams, the cartoon Dilbert writer, wrote a book titled How to Fail at Almost Everything and Still Win Big. The following list is an example of just that!

My All-Time Greatest Money Mistakes
  • Storing all my paper route money inside of trophies. That money never worked for me, and I often forgot it was even there.
  • Getting a credit card when I got to college so I could get a free t-shirt.
  • Using the credit card that I got at college for the free t-shirt. I had no idea that you had to pay that money back.
  • Using my credit card at college to buy things for other people, having them pay me cash, then spending the cash.
  • Taking out student loans in graduate school that I did not need to lease a new Ford Explorer.
  • Leasing two Ford Explorers.
  • Not contributing to my first workplace 401K for over two years because “I needed” that money.
  • Getting into $15,000 of credit card debt and having to borrow money from my Dad to get out of it (I paid him= back).
  • Buying our first home with 100% financing.
  • Getting lucky and selling that home before the market crashed in 2008, buying another home with 100% financing (2 loans).
  • Taking on a second loan for our home was almost 10% interest and had a balloon payment of $85,000 after 10 years.
  • Selling our first home rather than keeping it and making it a rental property.
  • Buying 5 new cars.
  • Not tracking our money soon enough.
  • Discovering we were spending $2300/mo on food for a family of 4.
  • Not investing more at a younger age, I did allow for the magic of compounding to work for me.
  • Keeping up with the Jones’s in general. Buying stuff that we thought we needed but didn’t make us happy.

Well, there it is. I am sure that I will think of more. When I do, I will add them to this list or write another post. I am grateful for each item on that list because I learned something from all of them, which I hope allows me to help others avoid those same mistakes.

Please share some money mistakes that you have made in the comments below. An important part of achieving financial independence is talking about money, good and bad. Leaning on a community of people with similar goals can help you get there faster!

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