“Personal finance…is more personal than it is finance.”
– Tim Maurer
"Did I just make a mistake?"
That’s never a question you want to be asking yourself. But let’s be honest—we all have. It’s a gut-punch moment, one that can shake your confidence and make you second-guess everything. I know because I’ve been there. And today, I want to share a story I’ve only told to close friends and family—until now.
It was June 2023, a quiet Sunday evening. My wife and I were at the kitchen table, going over our budget and goals for the next six months. After a long discussion, we agreed: we were staying put. No house hunting, no big financial leaps—just stability and a solid plan. We felt good about it.
The next day, we threw that plan out the window.
A house went up for auction. It was perfect—two acres overlooking Massanutten Mountain, two homes on the property with incredible income potential, and somehow, miraculously, within our price range. It was everything we had dreamed of for our family. Caught up in the excitement, I placed a bid.
I won.
And that’s when the nightmare began.
To spare you the gritty details: the kitchen was two inches out of level, the foundation was sitting in a foot of water after a rainstorm, and the walls were crumbling. The cost to make it livable was beyond our means. We had no choice but to back out—losing our $10,000 earnest money deposit in the process.
If I’m being honest, that was the lowest point of my life. Ten thousand reasons to be angry with myself, and ten thousand more voices in my head telling me I had failed.
I started avoiding decisions altogether. I didn’t trust myself anymore. The psychological effects of a bad financial decision are real. I became risk-averse, unwilling to take any step that might lead to another loss. Worse yet, I stopped caring. For the next six months, I ignored our budget, our goals—everything. I just didn’t want to deal with it.
Turns out, I wasn’t alone.
A study by Consumer Fed found the following:
Two-thirds of middle class Americans (67%) said that, in the past, they had made at least one “really bad financial decision,” and nearly half of those questioned (47%) acknowledged that they had made more than one bad decision. The typical (median) cost of these bad decisions was $5,000, but the average cost was $23,000. 1
Realizing that I wasn’t the only one who had made a costly mistake was eye-opening, but it also raised an important question: how do we move forward? How do we recover from financial missteps and regain our confidence?
- Forgive ourselves.
You may have heard the saying “familiarity breeds contempt”. Well, I would say unforgiveness does the same. Except in the case of personal financial mistakes, that contempt is aimed right back at you. It’s impossible to find resolve while struggling to fully forgive yourself.
- Determine the motive.
Now, this isn’t to say that having a good motive excuses poor decision making, but it will give you insight as to why the mistake was made. I would argue that honesty is the best policy here. Whatever you motive, good or bad, be honest with yourself. That’s a far better antidote than pointing fingers.
- Revisit your plan to determine your best course forward.
This is the last step of the process and cannot be effectively accomplished until you’ve done the work of forgiveness and digging up the motive. Many of us may have the inclination to get right back to the numbers, but for significant setbacks/emotional tolls, numbers won’t fix anything, not yet at least. This might be the time to pull in a professional, I did, and it helped so much.
Moving forward does take patience. Recovery will take time and discipline. But setbacks don’t have to define your future—they can refine it. If you stay committed to your plan and take small, intentional steps forward, progress is still possible.
For us, that journey took time, but we kept pushing ahead. And now, later this month, my wife and I will close on our first home. Our daughters are finally going to get that yard we’ve been praying for—a place to grow, play, and make memories.
Stay the course. Even if the road gets rocky, I promise you—it will pay off.