For Ron Lieber, the path to his latest book began with an otherwise straightforward question on a car ride home from a family trip with his then-four-year-old daughter. “She asked me why we didn’t have a second home, and I was stumped into silence,” Lieber recalls. “She was old enough to ask, but barely enough to understand the concept – I didn’t know what to say.”

While some readers responded to this anecdote in Lieber’s New York York Times column, “Your Money,” with derision, the incident underscored the author’s intention in writing his newly-released book, The Opposite of Spoiled: Raising Kids Who Are Grounded, Generous, and Smart about Money. “We need to end an epidemic of silence around money in families. We have a mistaken impression that talking about money will lead to money-grubbing children – but money does not subvert values,” Lieber insists.

But how did a personal finance columnist find himself dispensing advice about kids and wealth? The better question may be: how did Lieber find himself to be a personal finance columnist in the first place?

“I was a kid whose social class changed midstream,” reflects Lieber. After his parents’ divorce, (“Itself an economic event,” Lieber notes) his father lost his job and he and his siblings went from ‘the kids who had’ to the ‘kids who had less.’ Finding ways to beat the system – first of financial aid as a college student, then of frequent flyer miles in his 20s – became the norm. While others might lament needing to keep such close track of their finances, Lieber credits his family’s change of economic situation with having forced him to figure out the kinds of topics he addresses in his column.

Eventually, Lieber noticed a theme cropping up again and again from his readers – parents who followed his column began sharing some of the “crazy and hard” questions that their own children were asking about money, and Lieber would take a stab at providing an answer, then asking readers to improve them. “There were some complicated conversations in their communities. People with more were starting to feel demonized, as if they had to apologize for their wealth and their kids,” says Lieber. “People with less felt like their noses were being rubbed in everyone’s good fortune. They thought I might be a good person to come in and set everybody straight.”

Lieber recalls a strong and vibrant Jewish upbringing, and as a child, was a member of  Temple Shalom, Chicago’s largest Reform congregation. As co-president of his synagogue youth group, Lieber was certainly involved, but points out that this was a time “before the mitzvah project, before Jewish Teen Funders Network, and before communities began to redouble their efforts to connect Jewish values with the idea of a more modest way of living.” Lieber “would have welcomed the opportunity to wrestle with this stuff a little more,” which is today well-tackled in the growing field of Jewish teen philanthropy. “It’s connected to the realities in terms of the way these kids live,” says Lieber. “I visited the Seventh Grade Philanthropy Fund [at Brandeis Hillel Day School in the San Francisco Bay Area] and it was completely inspiring. In addition to giving 13 year olds adult responsibilities and seeing them rise to the occasion and evaluating adults that come to them for money, it’s a lesson for tradeoff: Who is most in need? Who are we to make that decision? What do we need to know about the world in order to make a good choice? It’s so spectacular in so many ways.”

Of course, not all parents find themselves in the position to discuss family finances in the same way. As is easily evidenced in the responses to Lieber’s columns, parents have found (or not found, as the case may be) many ways to broach financial issues with kids. Some take early opportunities to teach their children good practices, some wait until the need arises, and others aren’t sure where to begin. “Talking about money in all sorts of ways is a fantastic way to teach them all the values – like patience, modesty, generosity – that add up to the ‘opposite of spoiled,’” Lieber says.

To get the best of Lieber’s counsel, you’ll have to read The Opposite of Spoiled. But what advice does this father have for parents worried that it’s already far too late to raise the tricky topic of money with their kids? “Kids love participating in adult conversations,” he says. “It gets their brains working in new ways. Parents forget that they’re in charge, they make the rules. We have more power than we may think. The die isn’t permanently cast.”