Alison and Bruno, a couple in their early 40s, had been married for 14 years and had a 12-year-old daughter, Sara. Bruno’s software company, which he’d founded in graduate school, had become immensely profitable, and he’d moved his family into a big house in an elite part of Toronto. Increasingly, he and Alison found themselves at odds over how to spend their money, particularly when it came to Sara. Bruno suggested they seek outside help, hoping to find common ground in the parenting of their daughter.

Bruno’s parents were solidly middle-class people whose own parents were Italian. The second of three children, Bruno had grown up happily in southwestern Ontario,  leaving home to attend university.  He’d had summer jobs since he was 12, and had saved enough to pay his own tuition.

Alison, the younger of two daughters, had grown up in Rosedale, attended private school in Switzerland, and traveled widely. So had her sister, but the two girls were drastically different.  Studious, kind and rather shy, Alison loved animals and wore her privileged life discreetly. Her sister, on the other hand, felt entitled and could be obnoxious and demanding, She had an insatiable desire for the finer things, got a car at age 16, and had her own luxury apartment in first-year university—all at her parents’ expense. She had no qualms about making a scene when she didn’t get what she wanted.  Alison was frequently embarrassed, and attributed her sister’s character and behaviour to their parents’ indulgence.

As a result, Alison carefully limited their financial expenditures on Sara. Bruno, on the other hand, wanted Sara to have the best—all the things his own family couldn’t afford when he was growing up—and he didn’t understand why Alison believed Sara would inevitably end up like Alison’s sister.  They argued over birthday gifts, clothing allowance, even private tennis lessons. Alison agreed that they needed help.

I encouraged Alison to remember her sister at 10, and to compare her daughter to her sister in very specific ways. “Actually,” Alison said, after we’d gone through that exercise, “Sara’s much more like I was at that age—reserved and quiet and polite. She works hard at school, and she’s a thoughtful child.” Sara was very keen on sports—just like Alison’s sister—and on skiing in particular. Bruno wanted to buy her the best equipment and take her to Whistler at Christmas for expert instruction. He suggested they join one of the private ski clubs north of the city, and buy a condo nearby. Alison agreed that Sara would probably thrive, but worried that her daughter would turn into a mini version of her sister: spoiled, indulged, unmotivated.

It didn’t take long for Bruno and Alison to work out a way to bring skiing into their lives.  They’d rent a condo in ski country, and they’d all take lessons together. Each month they’d sit down and evaluate Sara’s growth in confidence, expertise and choice of friends. If they found that she was not healthily engaged in club activities, wasn’t committed to improving, or they didn’t like the direction her social life was taking, they would reconsider.

Alison had always been drawn to Bruno’s unpretentious “normalcy” and work ethic and wanted Sara to be that way, too.  Bruno felt reassured that Alison was increasingly able to see Sara as she really was, not as the inevitable clone of her sister. Resolving the skiing issue took pressure out of other financial and parenting decisions, and gave them a template for how to think about such things.

The last time we spoke, Bruno had embraced the sport as well, and the whole family was planning a winter trip to reconnect with Bruno’s working-class relatives in northern Italy—an area that also happened to offer excellent skiing.