My Most Mortifying Money Moment

You had to do something bad to wind up like this!

“The rate at which a person can mature is directly proportional to the embarrassment he can tolerate.”
–Douglas Engelbart

I knew better. When I was a carefree bachelor stationed in Germany, I lived life to the hilt. I traveled a lot. I went out a lot. I charged a lot.

So, when I came back to the States and sold my car, I paid cash for its replacement and used the remainder of the proceeds to pay off my credit card debt. I was debt free.

Just eighteen months later, I was on the phone with my soon to be fiancé, confessing to being saddled with five digits of credit card debt and only a semester into law school. She, on the other hand, was a paragon of financial virtue and had no such consumer debt, only a car loan.


Fortunately, she didn’t let that stop her from committing to me. Thank goodness. It also gave me the impetus I needed to stop the madness and arrest the slide.

Few things are as humbling as admitting your failings to someone you so badly want to impress. – Click to Tweet

That was tough medicine admitting my financial failings. I had earned good money in the Army yet had little to show for it, and it wasn’t like I could point to things which had gone on my credit card and say “boy, that was worth it.” Instead, I’d nickeled and dimed myself into quite a daunting credit card bill with nothing to show for it.

“But I’m going to be a lawyer and make a ton of money!” I’d tell myself in my weak moments, which were often, to rationalize my decisions.

I never became a lawyer. In fact, I never even finished law school, becoming, instead, so enamored with business school that I eschewed the JD/MBA program just to finish my MBA.

It took that moment of mortification to drive me to change my behavior. Few things are as humbling as admitting your failings to someone you so badly want to impress.

Then again, few reliefs are as great as the feeling of having the burden of debt lifted from your shoulders. If you’re in debt, I hope you get to have that feeling, as it’s liberating. If you’ve never been in debt, then don’t go seeking to get that feeling of relief. It’s the exact same feeling of relief as the one that you get when you stop banging your head against a wall. Your head feels better because it’s not receiving repeated blows. However, all of the banging which happened to get you to that point sure does hurt.

What’s your most mortifying money moment? Tell us about it in the comments below. No stone throwing. We’ve all been there.

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Jason Hull was the co-founder of Broadtree Partners, a firm that acquires $1-5MM EBITDA companies. He also was the co-founder of open source search consultancy OpenSource Connections, a premier Solr and ElasticSearch firm. He and his wife FIREd (financial independence retire early) at 46 and 45, respectively. He has a BS from the United States Military Academy at West Point and a MBA from the University of Virginia Darden Graduate School of Business. He held a CFP certification from 2015 - 2021. You can read more about him in the About Page. If you live in Johnson County, Texas or the surrounding areas, he and his wife are cash buyers of Johnson County, Texas houses.

4 thoughts on “My Most Mortifying Money Moment

  1. Yes, our financial mistakes can be humbling if we don’t continue to stick our heads in the sand and ignore them. Humbling is good because it means we’re paying attention, and you really wanted things to change. I’ve been in cc overwhelm also – but no more. As a Certified Money Coach for Women & Couples I love helping people pull the covers back on their money challenges, understand where those problems started (yes, it isn’t mom and dad’s fault, but it starts at home) and create step-by-step change.

    1. Hi, Lynn! Thanks for stopping by!

      I agree that there usually is some underlying script or limiting belief which prevents us from doing what we know we should do, and we’ve probably had that script for so long that we don’t even know or realize it’s there, much less how it started. Personal finance, from an academic point of view, is not that hard. Money in > money out. Yet, a lot of us have no idea where the script started, don’t know that it exists, and, therefore, have trouble getting over it. It’s 20% knowing what to do, and 80% beating our Monkey Brain to do what we’re supposed to – part of which includes exposing and overcoming those limiting beliefs and scripts.

  2. Same story, different service. USAF 1999-2006, practically nothing financially to show for 7 years of decent salary and 5 years of flight pay. UT MBA 2008. My most mortifying money moment? Other than blowing $2k on an ill-advised MLM while still wearing blue (my first foray into the business world) and $5k on a private pilot’s license, I would have to say it would be taking out additional student loans because I was naive enough to rely on the VA being expeditious about disbursing GI Bill money.

    1. I understand the allure of MLM. It seems like you can make a great deal of money if you’re successful. I think I read that somewhere between only 1-5% of MLM reps are profitable.

      Sorry to read of the VA bureaucracy. I wish I could say I was surprised. At least a MBA from UT Austin is a good one with a reasonably good chance of a positive ROI.

      Thanks for commenting and for your service!

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