A List of Dumb Things I’ve Done With Money

6 min read
March 14, 2023

Piggy bank wrapped in bandages with spilled coins underneath it


 I’m a financial advisor. And you would expect me to be good with money. It’s kind of a requirement for the job.

And before you start worrying, you can relax… I am indeed good with money.

But I wasn’t always. And even today, I’m not perfect. When working with a professional in any context, it can be tempting to feel like you’re the only one with challenges. It can be easy to feel alone and critical of yourself.

You might feel like everyone has this money stuff figured out, especially your financial advisor. This can lead to feelings of shame or discouragement around money.

Here’s a secret: no one is perfect when it comes to money. We all make mistakes and we all have room to grow.

One thing I am very focused on is helping folks let go of shame and judgment related to money. And so I thought it would be fun to be a little bit vulnerable and demonstrate how imperfect I am when it comes to money.

Just like many of us, I have a history of making less-than-stellar financial decisions. But I’ve learned from those decisions and have seen them as opportunities for growth.

If you struggle with feelings of shame around money, I hope that seeing my speed bumps along the way will help you feel less alone.

So here are some of the dumb things I’ve done with money!

Racked Up a Bunch of Credit Card Debt That I Couldn't Pay

One of the first negative memories I have about my own finances is when I racked up a bunch of credit card debt in college and shortly after. I don’t remember the exact amount but I’m 99% sure it was over $50,000.

I also had a bunch of different cards and played the balance transfer game by moving debt from one card to another in an effort to avoid high-interest rates (which eventually caught up to me).

So what did I buy with all those credit cards? It wasn’t one big purchase or anything (with one exception that we’ll talk about next). It was death by a thousand cuts.

It was eating out, electronics, furniture, travel, and generally just living off credit cards without any sort of budget whatsoever.

I treated my credit cards like a never-ending supply of money and gave no thought to the fact that I would eventually have to pay it back.

Eventually, I did pay it back. But it took years and lots of discipline to stay focused on it. When I finally paid off my credit card debt, I felt an incredible sense of accomplishment and vowed to never go into credit card debt again.

Put 100% of Trade School Tuition on a Credit Card

This is technically part of the previous point but it was so crazy that it deserves its own section. After college, I owned a digital marketing agency and was continuing to grow that business. But I was also interested in a part-time career in the wellness industry.

So what did I do? I dropped $6,000 on a credit card for a training program in this field without a second thought. I finished the program and worked for a while in this field and then stopped after a few years.

It was a great experience that led to an incredibly rich community of friends and opportunities. But paying off the card at over 20% interest was not awesome.

In retrospect, I had other options (like a payment plan) that would have saved money and made a lot more sense but I was feeling impulsive so I got to pay lots of interest for years as a result.

Mixed Business and Personal Funds

I’ve mentioned that I owned a digital marketing agency for many years before selling it and growing into my career as a financial advisor.

These days, I consider myself pretty darn business savvy and I consult with business owners on a regular basis.

However, that savviness took some time to acquire. In my less-savvy days, I was pretty horrible about mixing business and personal finances. I did the very thing that I now caution business owners against – I treated my business like a piggy bank.

I pulled money out for all sorts of things that weren’t always business related. Not only was I doing harm to my business, but I was also destroying the “corporate veil” that was designed to provide liability protection to me. If there had been any sort of major lawsuit or liability issue, my personal assets would likely be fair game because of my poor management of business funds.

Luckily, that’s all in the past. But I still look back on those days with a cringe (and thankful that I didn’t get myself in more trouble)!

Didn’t Pay My Quarterly Estimates

I harp on quarterly estimated taxes a lot. And for good reason. I’ve seen so many business owners and freelancers get into a pickle by not paying their quarterly taxes.

Two of the biggest issues that come from not paying quarterly taxes are:

  • Your cash flow is ruined because you have a huge tax bill in April.
  • You get hit with penalties for not paying on schedule.

Once you get behind, it can be very difficult to get caught up.

So guess what I did for years? You guessed it: did not pay my quarterly estimates.

I distinctly remember some years when I looked at my five-figure tax bill and just sank into depression because I didn’t know how I was going to pay it.

Of course, now I make taxes part of my budget, and how I structure my bank accounts.

But back in the day, I was really good at ignoring the advice of my accountant which resulted in penalties and big tax surprises.

Lesson learned!

Overdrafted My Checking Account

Of all the “dumb” things I’ve done with money, this one is probably the one that I’m most ashamed of (there’s that shame again).

Yes, I have overdrafted my checking account more than once.

I’m pretty sure that 99% of people in this country have overdrafted their accounts at least once in their lives.

But there’s something about seeing that negative balance (along with the $35 “kick in the face” fee that goes with it) that can really destroy your self-esteem.

Back when I was less financially secure, an overdraft was pretty disastrous and was difficult to recover from. In later years it was more of an inconvenience but no less shame-inducing.

In theory, if you budget your money well and pay attention, you should never have to worry about overdrafting. But this is not how life works.

Everyone sometimes gets distracted. Everyone sometimes has “life happens” events that can lead to issues like this. No one is immune to making mistakes with money.

Learning From Money Decisions

So there you have it. A list of dumb things I’ve done with money. I’m sure there is more, but these are the things that stuck out most to me.

We all make mistakes with money. You may have your own list of things that you look back on with shame.

I encourage you to think about what you’ve learned from those experiences. How do you handle money differently today as a result of your past money decisions? How have these experiences strengthened your ability to build wealth?

While it can be hard to let go of criticism that we direct at ourselves, our past experiences with money can have a positive impact on our financial future if we unpack the lessons learned each time.

Michael Reynolds Headshot

About the Author

Michael is a CERTIFIED FINANCIAL PLANNER™ (CFP®) and owner of Elevation Financial, a fee-only financial planning and investment management firm serving progressive SRI/ESG investors.


Did you know XYPN advisors provide virtual services? They can work with clients in any state! Find an Advisor.