Olivia: A recent poll found that 64% of kids have absolutely no idea if their parents give to charity, or how much. For nearly two-thirds of children, family generosity is a total black box. Jackson: Wow, 64 percent? That's… a lot of silence. It feels like we're all walking on eggshells around the topic of money, especially with our kids. We're terrified of saying the wrong thing, so we end up saying nothing at all. Olivia: Exactly. And that's the central premise of Ron Lieber's fantastic book, The Opposite of Spoiled: Raising Kids Who Are Grounded, Generous, and Smart About Money. Lieber, who's a long-time 'Your Money' columnist for The New York Times and a multiple-time winner of the Gerald Loeb Award—basically the Pulitzer for business journalism—argues that this silence is the root of the problem. Jackson: It's interesting he wrote this. You'd think a top financial journalist would have all the answers, but he's been open about how his own kids' questions about money completely stumped him and made him question everything. Olivia: That's what makes the book so authentic. It’s not a lecture from on high. It’s a field guide from a parent in the trenches who decided to use his reporting skills to find real answers. He argues that our discomfort is creating a generation of kids who are unprepared for the financial realities of the world. Jackson: Okay, so this isn't just about teaching them to save their pennies. This is a bigger mission. Olivia: It's a manifesto against silence. The core of our podcast today is really an exploration of how to transform money from a taboo topic of anxiety into our most powerful tool for teaching children about values, responsibility, and what it truly means to live a good life.

Jackson: So why are we all so quiet? Is it just awkwardness, or is there something deeper going on? I know when my son asks, "Are we rich?" my brain just short-circuits. Olivia: That's the universal fear, isn't it? Lieber says it comes from a good place. We're afraid that if we talk about money, we'll raise materialistic, "money-grubbing" kids. We want to protect their innocence. But he argues that in today's world, with social media showing off curated wealth and college costs soaring, silence is no longer a viable strategy. It's actually a form of neglect. Jackson: Neglect? That's a strong word. Olivia: It is, but he backs it up with one of the most powerful stories in the book. It’s about a high school sophomore named Jacob Swindell-Sakoor who was invited to give a keynote speech at an education conference. Jackson: A high schooler giving a keynote? Good for him. Olivia: Right. And he gets up in front of all these adults—teachers, administrators—and he just lets them have it. He says that when adults dodge kids' questions about money, they are being "completely irresponsible." And then he drops this incredible phrase. He calls it "blatant institutional adultism." Jackson: Hold on, what on earth is 'institutional adultism'? It sounds serious. Olivia: It is. It’s the idea that adults, as a system, are disrespecting and disempowering young people by withholding crucial information they need to survive. Jacob’s killer line was, "But how can we be the future if you’re not going to teach us about money, which is our future?" Jackson: Wow. That is a mic drop from a teenager. It completely reframes the issue. It’s not about our comfort; it’s about their future. It makes my "uh... it's complicated, son" answer feel pretty weak. Olivia: And that's Lieber's point. Kids are smart. They're trying to figure out the world, and money is a huge, mysterious part of it. When we're silent, they don't stop being curious. They just go find the answers somewhere else, probably from a friend who knows just as little as they do, or worse, from the internet. Remember the story of Kaden, the 13-year-old who looked up his financial planner dad's salary on Salary.com and came back with a wildly inflated number? Jackson: Oh man, I can feel the sweat on that dad's brow. It's the ultimate "gotcha" moment. So what's the alternative? Do we just hand them our tax returns? Olivia: Not necessarily. Lieber offers a simple, brilliant tool to start the conversation. When a kid asks a tricky money question, like "Are we rich?" or "How much do you make?", the best first response is another question: "Why do you ask?" Jackson: 'Why do you ask?' That's it? Olivia: That's it. It’s genius because it does two things. First, it buys you a second to think. Second, and more importantly, it reveals the real question behind the question. The kid asking "Are we rich?" might not be asking for your net worth. They might be asking, "My friend's family just got a new boat, are we going to be okay?" or "I saw a homeless person on the street, could that happen to us?" Jackson: Huh. That makes so much sense. You're not answering the literal question; you're addressing the underlying anxiety or curiosity. It turns a potential interrogation into a real conversation. Olivia: Precisely. It’s about arming them with information. As one expert in the book says, "This is human self-defense!" We wouldn't send them out into the world without teaching them to look both ways before crossing the street. Why would we send them out without any financial literacy?

Jackson: Okay, so we need to talk. The most common way we "talk" is through allowance. But I get the feeling Lieber is about to blow up my whole system. I've always paid my kids for chores. It felt... right. Isn't that how the real world works? Olivia: You're not alone. The book cites surveys showing that somewhere around 89 percent of American parents tie allowance to chores. It feels intuitive. But Lieber makes a compelling, counter-intuitive argument. He says chores and allowance should be completely separate. Jackson: Completely separate? So you just... give them money for breathing? That sounds like the very definition of entitlement. Olivia: I know, it sounds radical. But here’s the reframe: Chores are what we do because we're part of a family. We all contribute to the household. You don't get paid to take out the trash for the same reason your kids shouldn't. It's a shared responsibility. Allowance, on the other hand, is purely a teaching tool. Jackson: A teaching tool for what, exactly? Olivia: For learning how to handle money. Lieber wants us to think of allowance as a financial flight simulator. It's a safe, low-stakes environment where kids can practice budgeting, saving, and even making dumb mistakes without crashing a real 747. The goal isn't to pay them for work; it's to give them hands-on experience with financial decision-making. Jackson: A financial flight simulator. I like that analogy. So how does this simulator work? Olivia: The classic model he champions is the three-jar system: Spend, Save, and Give. Every time they get their allowance, they physically divide the money into these three clear, visible containers. The 'Spend' jar is for immediate gratification—the candy, the small toy. The 'Save' jar is for bigger goals, teaching patience and delayed gratification. And the 'Give' jar introduces the concept of charity and thinking beyond themselves. Jackson: And the mistakes part? That's the piece that makes me nervous. What if they just blow it all on junk? Olivia: That's the whole point! Lieber would say, "Let them!" He tells this fantastic story about a financial planner named Cheryl Holland. She decided to give her high school daughter her entire annual clothing budget in one lump sum on a debit card. Jackson: Oh, I can see where this is going. Olivia: You bet. The daughter immediately went on a massive shopping spree at PINK Victoria's Secret. Bought a ton of stuff. A few months later, she'd outgrown some of the pricey jeans she'd bought. The money was gone, and she had nothing to wear for the rest of the year. Jackson: That's a parent's nightmare. What did the mom do? Olivia: Nothing. She let her daughter experience the full, searing regret of that bad decision. And what happened? The daughter transformed. She started watching for sales, using coupons, earning extra money for things she wanted. She became, in her mother's words, an "excellent shopper." She learned a lesson in that low-stakes environment that will serve her for the rest of her life. Jackson: Okay, that's a powerful lesson. Learning from failure when the stakes are a pair of jeans, not a mortgage payment. The flight simulator. I get it now. It’s not about the chores; it’s about the choices. Olivia: Exactly. And it's about building financial muscle memory over a decade or more. As Lieber says, "We parents are in the adult-making business after all."

Olivia: And that idea of learning from experience is the perfect bridge to the biggest question of all, the one that keeps so many parents up at night: how do we stop our kids from becoming spoiled? Jackson: Ah, the million-dollar question. I'm immediately thinking of that classic bit with Chris Rock and Jon Stewart. Stewart is agonizing over his kids being rich, and Rock just deadpans, "My kids are rich. I have nothing in common with them." It's hilarious because it's so painfully true. Olivia: And Rock's solution? To send his kids to "Camp Kick-Ass" in Harlem to get their lunch money taken and get beat up a little. Jackson: Every parent in a comfortable suburb laughed and then thought, "Is there a waitlist for that camp?" We're all terrified of raising these little tyrants who've never known real hardship and have no perspective. Olivia: Lieber's answer isn't quite 'Camp Kick-Ass,' but it's not far off in spirit. He talks about the power of "symbolic deprivation." It's about intentionally creating experiences that strip away the non-essentials and remind kids what they actually need to be happy. Jackson: Symbolic deprivation. Sounds intense. What does that look like in practice? Olivia: He tells the story of Pine Island Camp in Maine, a place that's been running since 1902. The boys sleep in open-sided tents. There's no electricity. Bathing happens with biodegradable soap in the lake. The camp director says their motto is, "We don’t think about stuff, we think about soul." It’s a total reset button. Jackson: That sounds amazing, but most of us can't send our kids to a 100-year-old rustic camp in Maine. What's a more accessible version of that? Olivia: This is where the book gets really profound. It's not about manufacturing fake hardship. It's about engineering real perspective. He highlights the Manhattan Country School in New York City, which has this incredible tradition. They take field trips to each other's homes. Jackson: To each other's homes? Olivia: Yes. The school has a sliding tuition scale, so the student body is incredibly diverse economically. One week, a group of five-year-olds might be visiting a classmate in a sprawling Upper East Side townhouse. The next week, they're taking the subway to visit a friend in a housing project in the Bronx. Jackson: Wow. That's... incredibly powerful. They're literally walking in their classmates' shoes. Olivia: They trace their classmate's daily commute. They see their neighborhood, their playground, their bedroom. The teacher said the goal is for them to find commonalities. They might notice, "Hey, you have Legos, and I have Legos!" It breaks down the walls of assumption and builds genuine empathy. Jackson: That's it, isn't it? It’s not about making rich kids feel guilty. It's about making all kids feel connected. It's about understanding that "normal" looks different for everyone. As one sociologist in the book says, we need to be honest with our kids that life isn't just about merit. There is luck, and circumstance, and the family you were born into. Olivia: And that honesty, that perspective, is the ultimate antidote to being spoiled. It fosters gratitude. The book is filled with research showing that grateful kids have higher grades, better life satisfaction, and lower levels of envy and depression.

Jackson: It's amazing how it all connects. It starts with just breaking the silence, then moves to creating that 'financial flight simulator' with allowance, and finally, it's about grounding all those practical lessons in the deeper values of gratitude and perspective. Olivia: It all comes back to conversation. These aren't one-time lectures; they are ongoing dialogues that evolve as our kids grow. Lieber's ultimate point is that our spending, saving, and giving habits are a living record of our values. Our kids are watching, and they're learning from what we do, but even more from what we say about what we do. Jackson: So the takeaway isn't a 10-point plan. It's a shift in mindset. Money isn't the goal; it's the curriculum. It’s the language we use to teach some of the most important lessons in life. Olivia: Beautifully put. And the book is so hopeful. It argues that we can raise a generation that is more grounded, more generous, and smarter about money than we are. Jackson: I love that. Maybe the first step for anyone listening is just to start a small, simple conversation. Forget the big, scary "Are we rich?" question for a moment. Olivia: What would you suggest? Jackson: Maybe just ask your kid at dinner tonight, "What's one thing you're grateful for today?" Or, "If you had ten dollars to give away, who would you give it to and why?" See where that conversation goes. It's a small start, but it opens the door. Olivia: That's a perfect first step. And for our listeners, we'd love to hear from you. What are some of the money rules or rituals in your family? What's the funniest or most challenging money question your kid has ever asked you? Let us know on our social channels. We learn so much from this community. Jackson: Absolutely. This is a topic where we're all just figuring it out together. Olivia: This is Aibrary, signing off.