Real Insights: Trust, Freedom, and the Future—A Conversation with Lenore Skenazy
This interview is part of the R Street Institute’s new Real Insights series, featuring deep conversations with a diverse range of experts, authors, and leaders about the intersection of leadership and issues critical to our civic discourse, democracy, and culture. We will release a new interview every three weeks and you can find them all here. Want to speak with Erica? Please contact pr@rstreet.org.
Introduction
How do we build a world where trust—not control—defines how we lead, work, and live together? I revisit this question often, whether I am considering governance, organizational leadership, or even the subtle ways we raise our children.
That is why my conversation with Lenore Skenazy felt so relevant. Lenore, founder of the Free-Range Kids movement and co-founder of Let Grow, has spent years pushing others to rethink childhood, independence, and risk. What struck me within our discussion was how clearly her insights resonate beyond parenting, speaking directly to the broader questions our society faces around trust, agency, and our impulses to optimize for control rather than growth.
Our conversation deepened my thinking around how we prepare not just children, but ourselves, for navigating a complex, uncertain future. If we want institutions and societies that can thrive amidst uncertainty, we must begin with trust. And, that process starts earlier than we might think.
Key Insights:
Surveillance and the Erosion of Trust
Lenore shared a simple but profound insight: “It’s not certainty that gives you peace of mind. It’s trust.”
Everywhere we look today there’s an obsession with certainty: tracking our children with apps, monitoring employees’ productivity, attempting to erase uncertainty from our lives. However, in seeking certainty, we’re actually dismantling the trust essential for healthy relationships, productive workplaces, and resilient democracies.
Lenore illustrated this dissonance clearly, imagining how it feels to be a teen: “If I said I wouldn’t go to the party and then I didn’t, is that because I’m trustworthy, or because you were tracking me? There’s no way to prove I’m the former when the latter is happening.”
This point resonates powerfully for me, both as a parent and as a leader. Leaders who insist on constant oversight—’butts in seats’ and keystroke monitoring—aren’t cultivating accountability. They’re undermining trust.
“When we normalize surveillance as ‘just checking,’ we redefine relationships—work, family, social—into something devoid of trust.”
To foster responsibility, we must give people room to demonstrate trustworthiness. Yet, we’re designing a world that assumes distrust as its default.
Kids as the Canary in the Coal Mine
Lenore pointed out something important: “Kids are always the canary in the coal mine when it comes to culture change.”
How we treat children reveals deeper truths about our society’s trajectory. Today, childhood is heavily supervised, overly structured, and increasingly risk-averse.
But democracy thrives when citizens are confident in their ability to navigate uncertainty, exercise initiative, and trust each other. If we teach children that the idea of risk is inherently dangerous and bad and independence something to fear, what kind of adults—and democratic citizens—are we creating?
“Liberty was foundational in our country, but it’s eroding rapidly for children. Anything justified as ‘protecting our precious children’ quickly leads to more surveillance, more control, more policing.”
At R Street, we’re focused on cultivating trust, pluralism, and the institutional guardrails that support democracy. Lenore’s perspective adds an essential dimension: to build robust democratic institutions, we must consider the culture we’re creating at every level, starting with childhood.
The Perils of Optimization
Lenore challenged our widespread fixation on optimization: “We’re optimizing for safety, but safety isn’t the only good in the world.”
This optimization fixation applies far beyond parenting. In institutions—including our own—there’s often a temptation to prioritize efficiency and control. But this can backfire, eroding the trust and autonomy that actually fuel creativity and long-term resilience. At R Street, we’re building a learning culture that values curiosity, experimentation, and pluralism. Lenore’s insight refocuses this: if we want democratic institutions rooted in trust, we have to begin by trusting the youngest among us.
Lenore cited a fascinating Yale study: parents intervened half as much when they were told children’s messy, frustrating experiences were valuable learning opportunities. That insight struck a chord because I see parallels in the workplace. We often believe more control and oversight are helpful, but, instead, they frequently stunt genuine growth.
“When adults optimize play by structuring every moment, it’s like putting kids under a Chuck E. Cheese dome. They might have fun, but they lose all the crucial, messy learning that comes naturally through unstructured play.”
Credible Optimism and the Role of Think Tanks
A theme I often return to is credible optimism—the belief that clarity and realism don’t have to mean cynicism. Lenore captured this idea in her classic straightforwardness:
“If you don’t have optimism, you might as well not have a think tank.”
She’s right. The future remains unwritten, yet public discourse frequently presumes inevitable decline. Think tanks, leaders, and policymakers can—and must—do more than diagnose problems; we must actively shape positive futures.
Lenore reminded me historically, optimists are usually proven right: “We fixate on negative outcomes and completely misjudge the odds.”
She further explained that when we approach life—especially childhood—purely through a risk-reward lens, we miss something essential. In parenting, if we weigh even a joyful, everyday activity like walking to school against the worst-case scenario of death, no amount of mental health, confidence, or wonder can outweigh that fear. Freedom never wins when our culture magnifies rare risks to the point where any risk feels unacceptable.
However, the problem goes deeper: the rewards that matter most—the feeling of a great day, a lesson learned, a flash of awe—are often intangible and difficult to measure. If we focus only on measurable outcomes (like grades or future achievements), we undervalue the very experiences that shape resilient, imaginative citizens. In this way, Lenore challenges us to reconsider how we weigh risks and rewards. This challenge extends not only to children but also to our entire civic culture. If we want robust democratic institutions, we need to nurture a culture that trusts individuals to navigate life’s uncertainties, not one that tries to eliminate them.
Final Thoughts: Why This Matters
My conversation with Lenore left me with an important insight: How we structure childhood shapes how we structure society. To build a democracy founded on trust, agency, and responsibility, we must instill these values early. That means resisting the urge to control every outcome; embracing risk and uncertainty; and remembering surveillance does not foster trust—freedom and responsibility do.
Lenore has already had a significant influence on the way our society thinks about childhood, but I think her insights go even further—they inform how we shape leadership, democracy, and the future itself.