The Worst Financial Mistake I’ve Ever Made

This blog is about Mr. Sense and me journeying towards financial freedom as Christians whose purpose is to glorify God. My husband and I try to make financial decisions based on (1) our core belief that all the money belongs to God and (2) our shared goal of financial independence long before we’re eligible for Social Security payments. I’ve written about lots of our frugal wins along the way, from bike commuting streaks to grocery deals. But my life hasn’t always been like this. In fact, not too many years ago, I made a series of serious financial mistakes that underscored everything that was wrong with my financial and spiritual mindset at the time. 

My hope in revealing my biggest, most embarrassing blunder to the whole internet is twofold. Ideally, anyone in the same situation will recognize the obvious warning signs and steer clear. And hopefully readers who may feel depressed and hopeless after falling for seductive scams or being victimized by unfortunate circumstances outside of their control can be buoyed by the knowledge that misfortune (or in cases like mine, pure stupidity) doesn’t have to be a life sentence. 

This really lame story begins with my falling for a charming older man when I was fresh out of college. I was so flattered by his attention and excited to go on actual dates to interesting restaurants and cultural events instead of meeting dudes who needed me to pick them up because their cars were broken down (this seemed to be a frequent problem for men in their early twenties). My new boyfriend always waved me off when it was time to pay the bill. He was knowledgeable about my chosen career and gave me lots of helpful advice in that area. This advice, paired with my strong work ethic and enthusiasm, helped me to quickly advance in my field.

My paychecks grew steadily and soon outpaced my then-boyfriend’s. With hindsight, I can see the red flags multiplying right around this time. Instead of being happy for me, Mr. Nonsense seemed a little annoyed with my success. When I received praise or a bonus at work, I found myself not mentioning it to him because I didn’t want to argue about it. It felt a little weird, but I figured he was just old fashioned. Lots of men would probably have bruised egos if their girlfriends out-earned them, right?

Meanwhile, my boyfriend was facing some financial headaches. It was never very clear to me what was going on. His phone was always ringing, but he never picked it up or even looked at who was calling. Once, I stopped by his apartment when he wasn’t home. The mailbox was overflowing and a summons notice about a bill was taped to the door. He blew off my questions. Without us talking about it, I started covering the tab for dates and incidentals. Fortunately, I was flush with cash by then and could easily handle a few extra restaurant bills. 

Mr. Nonsense was always helping out various family members with money problems, but he was soon comfortable asking me for cash to tide him over for bills. I had the money, and the amounts seemed pretty small. Plus, I knew he was a kind-hearted family type who was always helping friends and family with handyman jobs and bills.

Eventually, I realized how much I had been covering– thousands of dollars over a year or so. The romance was waning, and I felt frustrated and panicked whenever I saw the look on his face that meant he was about to ask for a small loan, which I knew wasn’t really a loan. 

I resolved to tackle the issue head-on instead of waiting for the next request. I asked him to go for a walk with me, and I told him I couldn’t keep writing checks. It was bad for our relationship, I said. I was mentally prepared for a difficult conversation, but it veered further off track than I had anticipated. 

“Wow. I can’t believe how selfish you are!”

He took his wallet out of his pocket, withdrew a few dollar bills, and tossed them at me. They fluttered down onto the sidewalk like dead helicopter leaves from a tree. 

“There you go, since that’s all you care about.”

He stomped off. I picked up the crumpled dollar bills off the sidewalk, feeling dazed. I didn’t hear from him for a week. 

I wish I could say the scales fell from my eyes immediately, but that’s not what happened. I fixated on his words: selfish, selfish, selfish. I didn’t want money to ruin a relationship with someone I cared about. 

Though it took a few more months, I eventually got my head screwed on straight and got out of what was obviously a bad situation, to the immense satisfaction of my friends who had been urging a break-up for years. I don’t have a ledger of the total cost, but it was bad. There were a million better uses for that money, and I failed to steward it properly. 

This whole scenario was an easily preventable error of judgment. I knew Michele Singletary’s rule about “playing banker to your baby,” and I ignored it because I was swept up in my feelings. I entangled myself financially with someone who wasn’t my husband, leading to unrecoverable losses. What a surprise!  

But… looking back, I think this experience was one of the most valuable money lessons of my lifetime. Growing up with responsible Christian parents, I lacked exposure to financial ineptitude. I didn’t know what “floating a check” meant, and I barely understood why credit card companies advertised low interest rates, because who pays interest on a credit card? 

In the long run, this experience taught me more about money management that I could have learned from any library book or lecture from my mom. I choose not to lament the wasted money and ill-conceived relationship. I paid out a bunch of money and received a  valuable financial education in return. 

Here’s the lesson I paid thousands of dollars to learn, but you can hopefully accept for free: Being wise with our resources isn’t selfish; it’s stewardship. Finally figuring that out was worth every penny it cost me. 


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