For many years, I hosted Friday night Shabbat dinner debates with my two kids and my two step-kids. The topic could be anything from “Should parents monitor their kids’ social media?” to “Is it the government’s responsibility to pay for college?” Often the kids, now all in their twenties, would request a different topic (“Do video games cause violence?” was a favorite), and I typically relented. The topic didn’t matter. My role, much to their frustration, was always the same: devil’s advocate. No matter the issue, I took the opposing view.
Over time, I realized I wasn’t teaching them how to win arguments. I was teaching them something far more important: intellectual humility—an appreciation for what they don’t know or can’t know. That capacity is especially essential at a time when many professors, high-school teachers, and social media “influencers” promote sweeping social theories and present their opinions as unquestionable truths.
When a high school administrator, for example, confidently announces that norms such as promptness or objectivity are “white supremacy values” (if you doubt this, consult the website of the National Education Association, the country’s largest teachers’ union), they are offering an opinion—a poorly reasoned one—dressed up as certainty. There is no shortage of analogues on the political right, where conspiracy theorists, entertainers, and podcasters pretend that they, too, have a monopoly on wisdom.
So how can we teach our kids to think critically, account for cognitive biases, know what they don’t know and wrestle with complex issues?
What follows are arguments I’ve had with my kids, lightly fictionalized in dialogue with a daughter, Ariella, an intellectually precocious university freshman. These examples illustrate the habits of mind that cultivate intellectual humility and the pursuit of truth.
1. Steelman the Opposition
ARIELLA: Dad, this super-conservative guy Jeremy at school says Trump is right to send in ICE after undocumented immigrants. He infuriates me.
DAD: What’s his reasoning?
ARIELLA: His reasoning is he hates immigrants. The cruelty is the point, Dad.
DAD: I bet he has a better argument than that. Remember Jonathan Haidt’s moral foundations theory? Liberals tend to emphasize compassion and fairness. Conservatives add loyalty, respect for tradition, and a sense of the sacred.
It sounds like your moral intuition is that people facing oppression or distress deserve the chance to stay in this country. His intuition might be that unlawfully entering the country violates his sense of fairness and our national sovereignty, which must be protected.
ARIELLA: So I have to buy into his moral assumptions?
DAD: Of course not. But you should know what they are and the strongest version of his argument. You may find he’s not such a bad guy, and it will sharpen your own thinking.
ARIELLA: Sometimes I just get so tired of your both-sides-ism.
DAD: The alternative is one-side-ism, where you stop examining multiple perspectives and just accept the first one that feels right.
2. Think Like a Bayesian
ARIELLA: Dad, you’re a big free trader so you must hate Trump’s tariffs.
DAD: I’m not a fan, and I’m worried. But who knows? Maybe they’ll work.
ARIELLA: Come on, Dad! You know refusing cheaper imports causes inflation.
DAD: I do think that. But what probability would you assign that tariffs might have some long-term positive effect?
ARIELLA: Ugh. Fine—30%, max.
DAD: So you’re acknowledging a 30% chance we’re wrong. I’d say 20%. Either way, we’re admitting uncertainty. Our economy is complex, and we might be missing something.
ARIELLA: Okay, then what are the chances you’re wrong about DEI being harmful?
DAD: There are studies that show that DEI programs fail to achieve their stated goals and actually generate resentment. But it’s largely a question of values, and such perspectives aren’t easily quantifiable. It’s like asking the odds that a human embryo has moral rights. One’s answer depends on moral assumptions that aren’t empirically testable or falsifiable. I’ll argue my view vigorously but I can’t assign it a percentage.
ARIELLA: The answer is zero, Dad.
3. Understand Tradeoffs
ARIELLA: I’m sick of drug companies bilking us. The price of insulin in the U.S. compared to Europe is disgusting.
DAD: I agree that we pay too much. But let me ask you something: Why does the U.S. invent so many more drugs than Europe, close to twice as many?
ARIELLA: What does that have to do with insulin prices?
DAD: Quite a lot. One reason we innovate more may be that companies know they can recoup R&D costs. Europe benefits from American medical research while its consumers pay less. You want more cancer drugs, don’t you?
ARIELLA: So we should just let drug companies get away with highway robbery?
DAD: I am not saying that. I want you to grapple with the tradeoffs. When we discuss price controls, we need to weigh the negative effects. We want affordability without killing the incentive for new breakthroughs.
4. Avoid Snap Judgments: “What Would Change Your Mind?”
ARIELLA: Dad, Israel bombed a hospital in Gaza. It’s horrible!
DAD: I saw the reports. But let’s not jump to conclusions.
ARIELLA: What could ever justify bombing a hospital?
DAD: First, we don’t know who caused the explosion. And if Israel did, we don’t know the intent. We don’t know whether Hamas used the hospital for military purposes. Let’s wait for verified information.
ARIELLA: Fine. But suppose the IDF did deliberately bomb a hospital.
DAD: I doubt that, but if solid evidence emerged, I’d be outraged. The point is to hold off until facts, not the shock of the initial horrific scenes, guide our judgment.
ARIELLA: I still don’t think it’s ever justified to bomb a hospital.
DAD: What would it take to change your mind?
ARIELLA: Two things. I would have to learn that Israel didn’t do it or that there were no patients in the hospital, just terrorists shooting from it.
DAD: Let’s wait and see, then.
Over time, I realized I wasn’t teaching them how to win arguments. I was teaching them something far more important: intellectual humility—an appreciation for what they don’t know or can’t know.
5. There Can Be More Than One Cause
ARIELLA: Dad, in my sociology class, we learned that more than a third of incarcerated people are black even though black Americans make up only 14% of the population. That’s pure systemic racism.
DAD: Why assume the disparity is solely due to systemic racism?
ARIELLA: What else could it be?
DAD: Harvard sociologist Orlando Patterson argues that in many inner-city neighborhoods, a small minority of residents—around 15%—generates a disproportionate share of violence and disorder. He calls it “endemic violence.”
ARIELLA: So he’s blaming black people for their oppression.
DAD: No. He’s offering another factor that contributes to violence and therefore incarceration rates. If you rule out cultural differences entirely, then structural racism becomes the only explanation by default for any disparity. But reality is often multi-causal.
ARIELLA: So which is it, culture or structure?
DAD: Probably some of both. Serious thinking requires parsing competing explanations, not settling with one.
6. Lived Experience is Not Enough
ARIELLA: When we deny one people’s claims of oppression, people will deny Jewish claims, too.
DAD: First, no group is monolithic. Not all black Americans or all Jews or all Latinos make the same claims. You’re hearing from a small sample at school.
And second, it’s okay to question lived experience—ours or anyone else’s. If reliable survey data show that young Americans are more supportive of Jews than I thought, I want to know. Lived experience matters, but it cannot automatically override every other form of evidence.
7. Some Things Actually are True
ARIELLA: My English professor has us deconstructing all kinds of texts. She challenges the idea of objective truth and says what we call “truth” is really shaped by language, culture, and power. She even argues that a lot of what we consider “knowledge” is just white men protecting their status.
DAD: You like your air fryer, don’t you? Or is that just a social construct?
ARIELLA: Seriously, Dad.
DAD: I am serious. Building an air fryer requires an accumulation of scientific knowledge like thermodynamics, circuitry, and materials science. If all knowledge were just a power play by elites, why would anyone develop technologies that help everyone, including poor people? Rational thought and the scientific method aren’t mere social constructions. They’ve produced massive improvements in human well-being.
ARIELLA: Fine, but you’re ignoring something. For centuries, universities and scientific societies were open almost exclusively to white men. They controlled who could publish, who got credentials, and who had access to labs. That dictated what was considered “real” knowledge.
DAD: You’re right that powerful people have shaped the boundaries of knowledge in self-serving ways. Your professor is giving you a valuable lens for understanding how institutions work. Just remember that it’s one lens even if she treats it as a one-size-fits-all explanation. It’s useful for spotting bias and exclusion, but it’s not a complete explanation of how knowledge is created. Don’t settle for a single tool in your intellectual toolbox. Use all of them.
Conclusion
Intellectual humility isn’t about doubting everything or watering down our convictions. It’s about recognizing the limits of our own understanding. The skills of intellectual humility—steel-manning arguments, assigning probabilities, identifying trade-offs, resisting snap judgments, acknowledging multiple causes, weighing lived experience against evidence, and distinguishing socially constructed ideas from actual truths—isn’t innate. It must be taught and practiced.
In a polarized age that rewards outrage, over-confidence, and absolutism, raising children who can pause, question, listen, and think is one of the most radical things we can do.
