Check out this wonderful first-person essay by Pat Jordan from Men’s Journal. Jordan writes how he learned about money from his father, a professional grifter:
In many ways, I am my father’s son. once, in my 60s, I told my father, in his 90s, that I was not much like him. “How so?” he asked. I said, “I never gamble.” He laughed, a dismissive laugh, and said, “You? A freelance writer for 40 years?” He was right. He had taught me how to con people early in my life. I used that knowledge in my late 20s to hustle pool like him. I wore construction clothes at lunchtime. I conned my marks into spotting me the eight and nine in nine ball, and if I lost I always went to the men’s room, climbed out a window, and left without paying. A lesson from the old man. “Always check the men’s-room window before you play,” he said. “Because even if you lose, you’re not gonna pay.” Years later, when I became a writer, I conned editors into giving me assignments. “You got to find out what they want,” he said, “then give it to them. Tell them anything they want to hear to get the assignment, then write it the way you want.”
He taught me so many things that became a part of my life, that determined how I lived my life. He taught me that only a fool believes in perfect justice. “There’s no such thing as an accident,” he said. “You’re supposed to know the other guy always runs the stop sign.” He taught me that a man never quits no matter how defeated he feels, that a man always has to have the courage of his suffering. And most important, he taught me that “there are only three vices in this world, kid: broads, booze, and gambling, and if you’re gonna do it right, pick one and stick to it.” I was in my 20s, with a wife and three kids, and there wasn’t much room in my life for vice. Years later, however, I had more than a passing acquaintance with one of those, and it wasn’t booze or gambling.
But in the one way that really mattered, to me anyway, I was not much like Dad at all. I never had his purity of understanding of the true nature of money. That has always shamed me. I have been burdened, conflicted, cursed, you might say, by my own fearful need to hoard money to forestall that looming disaster always around the bend, the foreclosed house from my youth.