Do you want your kids to feel comfortable coming to you when they make a money mistake?
Start with a confession, not a lecture.
Years ago, I told my kids about one of my dumbest money mistakes. I had been renting a small storage unit for a pile of old stuff that easily could have fit in my garage. Most of it probably should have been donated years earlier. By the end, that little unit was costing me $97 a month.
And every single month, when the charge hit my card, I had the same thought: “I need to cancel that.”
Then I did nothing.
Month after month after month.
I finally cleaned it out with help from my daughter and asked the front desk when I had first rented the unit.
Gulp.
I had been paying for pointless storage for 13 years.
My kids laughed at my idiocy. Fair enough.
But that conversation did something useful. It showed them that smart adults still do stupid things with money. It showed them that procrastination is expensive. And it showed them that in our family, money mistakes are safe to talk about before they snowball.
That’s the tip: if you want honest money conversations at home, skip the polished success story and tell the dumb one instead.
- The recurring charge you ignored for years.
- The subscription you forgot to cancel.
- The purchase you regretted instantly.
- The “great deal” that wasn’t. (Looking at you, 1984 Jeep Cherokee!)
Those stories do more than entertain your kids. They give them permission to bring you their own mistakes early, while the problems are still small enough to fix.
Tell one tonight.



