The other morning, I sacrificed my usual workout with my trainer and instead did something nice for my children. I went to a wealth management seminar at the Crescent Club, where the topic was how best to structure trusts for one’s progeny so as to influence the choices they make. Noblesse oblige, indeed. The attendees were all self-made multimillionaires, and all of us had more money than we were likely to spend in our lifetimes. The central question was: how do we give it to our kids without ruining them?

The seminar facilitator discussed strategies for dribbling out the dough to our kids at such milestones and in such amounts as to guarantee they lived their lives in accordance with our wishes. Graduate from college, get $250,000. Earn a degree in law or medicine, get $500,000. Marry the right kind of spouse, get $1 million. And if the kids wanted to trod some unconventional path—becoming a high school English teacher or, say, a journalist—you could supplement their income if they were following a sincere passion (as opposed to slacking it after failing to hit a higher trajectory).

Strangely, though, neither the facilitator nor my business-minded cohorts even paused to consider that the top-down management of one’s children’s lives could just as easily destroy their drive and perseverance as shoveling piles of money into their bank accounts. Will your son really work hard at his job knowing that simply by getting married he has more coming to him than his boss will earn in a lifetime? 

My father grew up in the Depression, in a factory town in the Midwest. The meals of watery soup and bread, the shoes that forever pinched, the toyless Christmases, the neighbor’s furniture piled on the curb—they twisted his soul’s outlook on the world into a fixed rictus of anxiety and fear, an unshakable belief that all one’s possessions were forever at risk of being snatched away. Therefore my childhood was haunted by Depression’s ghost. My brother and I shared our single-story ranch house with austerity and denial as our childhood companions, while my parents squirreled away every spare nickel my father ever earned.

We never went without, but watery soup and bread were replaced with canned food bearing white labels and black lettering, the first “generic” brands. The milk we drank was Carnation Instant, which we took turns whisking to smooth out the lumps (“made milk” we called it). This occupied our time while we waited for our bread to thaw enough that we could hand-pat it flat for the toaster. My mother bought day-old white bread loaves in bulk and piled them in the garage freezer. She dubbed it “diamond bread” because of the sparkly ice crystals.

I remember trying on a winter coat in a stranger’s driveway while my mother haggled over the garage-sale price. Nine years old, standing there in someone else’s coat while my mother counted out the change, my own soul’s smile tightened, and I swore my life would be different.

My life is different. Material want and shame are powerful goads to success, and I have succeeded, financially, beyond my parents’ wildest imagination. The property tax on my house alone exceeds the highest salary my father ever earned. I don’t bother to look at the prices on the menus at Dallas’ priciest restaurants. We get personalized Christmas cards each year from the Four Seasons corporate office. And our kids have more toys than a whole day care center could put to use.

But given the price of toys these days, they are essentially free—so when should you deny them to your children? In my parents’ case, it was easy: always. “No” was the default response to any question involving the procurement of a material good. The money wasn’t there. And whatever it was that we wanted, we didn’t need it. So they were spared the modern philosophical questions that most parents, and particularly the affluent parent, must ask themselves: how much should you give your children now, and how much should you leave them when you’re gone?

A saleswoman recently cajoled me into buying a $400 stuffed Hermès horse for my baby daughter—thereby answering the “How much now?” question. (That tingling sensation you felt was the electromagnetic charge caused by my father spinning at 5,000 rpm in his grave.) Daily doses of Hermès horses, Birkin purses, and Jimmy Choo shoes. The odd private jet charter to Aspen. That and the suicidal sailor dive of the stock market have probably rendered moot the “How much when you’re gone?” question.

On a positive note, my kids will have to develop the drive and perseverance to marry the children of my friends.

Write to martycortland@gmail.com.