Freedom With Boundaries
Shortly after the first wave of COVID-19, something unexpected happened in the wide-open spaces of America. The National Park Service began closing gates, not because the wilderness was unsafe, but because it had become too crowded. With gyms, restaurants, and theaters shut down, millions of people turned to the only open sanctuary they could find: the outdoors. We all craved freedom, and the national parks seemed to hold it.
But as crowds poured in, those landscapes of solitude and wonder began to buckle under the weight of too many footprints. Parking lots overflowed, trails eroded, wildlife grew agitated, and visitors who longed for peace instead found themselves elbow-to-elbow with strangers. So the Park Service did something counterintuitive: they shut the parks down, then slowly reopened them with timed-entry systems.
At first, it felt restrictive. Why should you have to schedule freedom? But the wisdom was clear. By saying, “Yes, when you reserve a slot,” the parks ensured that each person could encounter beauty without being overrun. The rules didn’t steal freedom; they protected it. The boundaries allowed the wildness to remain wild.
Sometimes, parenting feels much the same. We are stewards of a wilderness; our children’s emerging freedom, curiosity, and independence. And like the Park Service, we often face the challenge of balancing access with readiness, desire with responsibility. Our job isn’t to slam the gate shut with a hard “No,” nor is it to fling it wide open without thought. It’s to manage the flow with love, wisdom, and timing.
That’s where a simple phrase has reshaped my parenting: “Yes, when…”
The Power of “Yes, When”
Several years ago, my son asked for a TV in his bedroom. Everything in me wanted to answer with an immediate no. I had visions of him staying up all night, glued to cartoons, ignoring homework, drifting into isolation. It felt like a bad idea on every level.
But instead of shutting it down, I paused. I asked myself: What’s the real concern here? It wasn’t that the request itself was unreasonable, it was that he wasn’t yet showing the responsibility to handle it. So I shifted my answer:
Yes, when you show me you can keep your routines without reminders.
Yes, when you finish your chores consistently.
Yes, when you demonstrate you can balance freedom with responsibility.
It changed the whole dynamic. Suddenly, the TV wasn’t a forbidden treasure hidden behind a locked door. It was a possibility. One he could work toward by cultivating maturity. The responsibility shifted from me as the gatekeeper to him as the climber. If he wanted the summit, the trail was clear.
Over time, something beautiful happened. He began taking ownership of his routines. Not perfectly, of course. He stumbled plenty, just like any hiker loses footing on a steep trail. But his motivation grew, because he wasn’t just following rules to avoid punishment; he was climbing toward a dream. He was connecting consistently and discipline with his dreams.
When the day finally came and the TV appeared in his room, the victory wasn’t about electronics. It was about self-mastery, resilience, and the confidence that he had earned something by stepping into responsibility.
The Psychology of “Yes”
My instincts found later affirmation in Daniel Siegel and Tina Payne Bryson’s book The Yes Brain. Their research explores how a parent’s posture of openness, curiosity instead of fear, and responsiveness instead of reactivity shapes a child’s development.
They describe the “Yes Brain” as one that is:
- Receptive rather than reactive. It leans into challenges instead of shutting down.
- Resilient. It bounces back from setbacks because it isn’t ruled by fear.
- Open. It explores rather than avoids.
- Balanced. It learns to manage impulses while pursuing growth.
When parents create a culture of “Yes, when,” we model this way of being. We teach that freedom is not arbitrary but connected to readiness. We also communicate trust: I believe you are capable of growth, and I will help you get there.
Psychologists call this scaffolding. Just as climbers use ropes and anchors to explore heights they couldn’t reach alone, children need parents who provide both freedom and support, allowing them to stretch without falling into chaos. “Yes, when” is a belay system. It doesn’t eliminate risk, but it makes exploration safe enough to lead to growth.
Freedom With Guardrails
When my son eventually got his TV, it didn’t mean an endless stream of cartoons or late-night YouTube excursions. Freedom without boundaries isn’t freedom at all, it’s chaos. So we added guardrails: internet access shut off at a certain time, homework before screen time, shared family conversations about what was being watched.
This wasn’t about control for its own sake. It was about protecting what mattered most: his sleep, his education, and his relationships. The same way the Park Service limits visitors to preserve the wilderness, boundaries around privileges preserve their purpose.
Children, by nature, will push those edges. Not because they’re defiant, but because they’re explorers. They want to know where the trail ends, how sturdy the bridge really is, whether the rope will hold. Part of our role as parents is to let them test those boundaries safely; without letting them tumble off a cliff.
Guardrails give them the best of both worlds: the exhilaration of freedom and the security of structure.
The Danger of Reactive Parenting
The opposite of “Yes, when” is reactive parenting. Where our responses are driven by fear, frustration, or fatigue. In those moments, we say “No, because I said so,” or “Fine, whatever, just stop asking.”
Both extremes erode trust. Hard reactivity (always no) shuts down curiosity and teaches kids that desire is dangerous. Soft reactivity (always yes) fosters entitlement and prevents children from developing responsibility.
Responsiveness, however, listens, discerns, and collaborates. It acknowledges the request, names the concerns, and lays out a pathway forward. It says, “I hear you. I want to move toward your dream with you. But let’s do it in a way that helps you grow.”
In the mountains, reactivity is like scrambling off-trail in a storm, you risk injury or getting lost. Responsiveness is like studying the map, choosing the safest route, and pressing on with wisdom.
Raising Responsible Explorers
Every child longs for freedom the same way hikers long for ridgelines and climbers long for summits. And just like in the wild, those freedoms must be earned through preparation, endurance, and respect for the terrain.
Our job isn’t to keep them in the parking lot forever, nor to send them blindly into avalanche zones. It’s to help them build the skills, resilience, and maturity to walk farther, climb higher, and carry responsibility well.
This requires patience. Sometimes it means saying:
- “Yes, when you’ve practiced piano for a full month without reminders.”
- “Yes, when you’ve shown you can return the car on time and with a full tank.”
- “Yes, when your grades reflect steady effort, not last-minute scrambling.”
Each “when” is a milestone on the trail. And each completed milestone gives a child the deep satisfaction of accomplishment. They don’t just receive a privilege, they become the kind of person who can handle it.
Parenting as Partnership
What I love most about “Yes, when” is that it turns parenting into a partnership. It shifts the narrative from me versus you into us together against the challenge.
When my kids stumble (and they always do), it opens the door to rich conversations:
- “What got in the way this week?”
- “How do you think you could stay on track next time?”
- “What matters most to you about this goal?”
Instead of power struggles, we have coaching sessions. Instead of shame, we cultivate reflection. Instead of simply enforcing rules, we build resilience and self-awareness.
That, I believe, is how children grow into well-rounded, grounded adults. Not because they’ve been endlessly protected from risk, but because they’ve been trusted to grow into freedom, step by step.
Conclusion: The Trail Ahead
Parenting is less like guarding a fortress and more like guiding an expedition. We carry the maps, but our children carry the dreams. Our job is to keep them safe while also teaching them how to read the terrain for themselves.
Like the National Parks during the pandemic, sometimes we have to close the gates. Not to deny freedom forever, but to preserve its beauty for the right time. Sometimes we have to say, “Yes, when…” to help our children experience freedom in a way that shapes them rather than overwhelms them.
So let me leave you with this reflection:
What dreams are your children asking for today? What would it look like to turn your “no” into a “yes, when…” to give them both the gift of freedom and the growth that comes with it?
Because in the end, the greatest privilege we can give our children isn’t a TV, a phone, or a car. It’s the steady confidence that they can climb toward their own dreams; with wisdom, resilience, and hope.
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