My Worst Financial Mistake
And it has nothing to do with money.

My wife and I have recently been using a set of icebreaker prompts as an exercise to learn more about each other’s history. It’s been fun and has sparked quite a few rabbit hole conversations that would have otherwise never come up.
A question from last week was, “What is your biggest financial mistake?”
I’ve made plenty in my life, but three come to mind immediately.
My most embarrassing mistake was actively choosing to overdraft my checking account, with the accompanying $35 charge, to fill up my gas tank with $30 worth of gas.
My biggest monetary mistake was choosing to take out student loans in order to attend Butler University, a private school, when I could have gone to any state school in Indiana tuition-free due to my father being a disabled veteran.
My biggest overall mistake was not learning how to talk about money with my wife from a position of love, trust, and respect at the beginning of my marriage.
Instead, I had an approach that combined two bad financial attitudes, both of which (of course) were rooted in my childhood.
(Trying to) Be the Breadwinner
My first bad attitude the classic 1950’s assumption that the husband should be the breadwinner of the family, allowing the wife to stay at home and raise the children.
Looking back, this was definitely sourced from me being a child of divorce, raised by a single mom. My anger at my dad took on the form of rebelling by trying to be everything he wasn’t.
- I would be completely present with my kids, not absent like him.
- I would be completely sober, not an alcoholic like him.
- I would completely financially support my family, not abandon it like him.
The unfortunate consequence of these attitudes is that I took things to the extreme opposite of his behavior, which is just as unhealthy. Sometimes it’s worse, since we can be under the impression that we’re “doing the right thing.”
(For a deeper dive, read No More Mr. Nice Guy.)
Without getting too deep into my psyche, I was so focused earning enough money that I lost sight of how I could actually be a good husband and father.
There were multiple repercussions of this tunnel vision.
- I put undue pressure on myself to advance my career and increase my salary to the level necessary for the stay-at-home-mom arrangement.
- When I didn’t attain that income level, I was wracked with guilt that I was failing as a husband, a father, and a man.
- I didn’t support Amelia the way she needed, especially the first couple of years of marriage and parenthood.
- I ignored that Amelia truly enjoys her work and didn’t desire to be a stay at home mom in the traditional sense.
I was not a good partner those first few years.
Husband Knows Best
The second bad attitude I had was that I didn’t talk with Amelia about our financial goals or how to reach them. Reaching back again to my childhood, this probably stemmed from a) seeing my mom always worried about money and b) seeing her pretend it wasn’t a problem.
I tried my damnedest to mimic that nonchalance so Amelia wouldn’t be anxious about our finances. Ultimately, my attitude was quite selfish, as I didn’t want to feel the discomfort that comes with having the kind of hard money talks that all couples need to have.
Just like my previous attitude, my lack of communication completely backfired.
- It cut her off from giving her own financial input.
- It silenced her emotional status from the financial conversation.
The result of my foolish choices was that Amelia felt like she couldn’t talk to me about money without getting into an argument. And she was right. I was (and still am, to some degree) as stubborn as a mule.
So instead of trying to change something she had no control over, she decided to just let me have full responsibility of our finances. At first I was delighted (yes, I was kind of an ass), but then I started to really feel the burden of managing our finances that rested squarely on my shoulders.
That burden turned into misplaced resentment, which, when combined with the guilt I felt as described above, turned into lying about our overall financial health.
That lying caught up to me years later when I had made a didn’t tell her the true balance of our credit card. As has happened to liars throughout history, the person being lied to ultimately found the truth.
The worst part wasn’t the money that we owed.
The worst part was that I had broken her trust, and it would take a long time before I would start to get it back.
It has taken years of trial and error, with so many errors on my part, but we have gotten much better at communicating about money.
- We use You Need a Budget to track our expenses and plan for the future.
- We have one credit card for cash back, the Costco Citi card.
- We have weekly budget check-ins on Sunday afternoons.
Most importantly, we are talk constantly about what we buy, what we save, and what our financial future looks like.
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This article is for informational purposes only, it should not be considered Financial or Legal Advice. Not all information will be accurate. Consult a financial professional before making any major financial decisions.






