This is the best-ever piece I’ve seen here on The Billfold, bar none.
I’m glad you let your son come into his own, and you discovered for yourself that he was grown-up enough to take on grown-up responsibilities.
And like you, my parents were pretty terrible at managing money. Despite my father having a job in the upper levels of the Federal civil-service pay-grades (he literally could not have earned more without taking on a job managing hundreds of employees) they still managed to get into serious debt, despite living in a tiny house and driving ancient cars.
But all three of us boys turned out okay, money-wise, learning exactly the correct lessons from my parents’ struggles with money while we were growing up. (For them, the final “Come to Jesus” moment was when I finally convinced them to make an appointment with a local Consumer Credit Counseling Service affiliate after they asked my younger brother to loan them money out of his savings for “debt consolidation”.)
I don’t have any kids, but seeing the kids of others, I’m convinced that kids are largely gonna be themselves, and absent abject neglect (and sometimes in spite of it), there’s not a great deal parents can do to influence this. Make sure they experience life, don’t coddle them from the real world, and they’ll figure things out (or not).