Earlier this year, I stumbled across my children’s copy of Shel Silverstein’s Where the Sidewalk Ends and was struck by his invitation to step off the pavement and into the “soft white grass” where “the sun burns crimson and bright.” It dawned on me: In a world of never-ending to-do lists, an overcrowded inbox, and a noisy political landscape, I was searching for a place beyond the sidewalk — where play, reflection, and connection converge — and where deeper understanding grows.
So, after 26 years of teaching and leading, I carved out time to do something out of my routine: to become a student for a day.
Feeling Belonging
As a Head of Middle School at a girls’ independent school, I often think about how our systems, teaching practices, and school culture shape our students and their experiences. But I remain at a distance. To better understand not only what students encounter but how it feels to see the world from their perspective, I needed to step off the sidewalk of my job and into their world. So, in late March, I joined a willing seventh-grader and followed her schedule — fitness uniform packed, water bottle filled, heart racing like it was my own first day of school.
In the English classroom, my tablemates welcomed me warmly; I noticed just how relieved I felt that they had saved me a seat. We began with a “messy minute” writing prompt and then dove into a discussion of their favorite climactic moments in the text. Even though I had not done the reading, they included me easily, with no hint of judgment. That small act reminded me how powerful it is when students feel seen and accepted regardless of preparation or prior knowledge.
Later, while working on epistolary stories that blended fiction and research, my partner showed me how to navigate the library database. The quiet generosity of this moment stayed with me. Belonging isn’t just about seating charts or check-ins — it lives in spontaneous invitations and helpful gestures across a shared task. I found myself wondering how we might foster this kind of natural inclusion in every classroom every day. And how could we create more opportunities to spark our students’ imagination and invite their storytelling as they foster a greater sense of self?
My next stop was PE, a class I dreaded in my own middle school years. During the badminton drills, I was buoyed by the kind encouragement of my teammates —“You got this!” and “Good job!”— offered regardless of where the birdie landed. This supportive environment stood in sharp contrast to the judgment and anxiety I remembered. It made me wonder: How might we bring this same ethos of affirmation into our more pressured academic settings?
Fighting Fatigue
Midday, I returned to my office expecting to reset — but instead, found unexpected clarity. I looked at my desk, littered with half-finished notes, and saw just how fragmented my attention had become. I wondered: Is this a result of our growing reliance on technology? Or the increasing complexity of our roles as educators and caregivers?
I also noticed the fatigue from toggling between roles and settings. I had only experienced a few hours of it, yet I already felt the weight. What are we asking of our students as they navigate these constant transitions? And how might we better attune ourselves to the emotional rhythms of their days?
Being Flexible
After lunch came math class — and a quiz. I hesitated. Should I visit another class? Should I stay in my office and tackle my growing email inbox? I caught myself rationalizing the avoidance caused by my uncertainty. Not seeing myself as a “math person,” my instinct was to opt out.
But I went. As I worked through the quiz, I noticed I was skipping around, making thoughtful guesses, and trusting myself in ways I never had as a student. Perhaps it helped that the stakes were low — my quiz would not be graded. Perhaps it was also thanks to our math teachers who celebrate mistake-making and routinely remind us of the value of a growth mindset. Regardless, I wish my seventh-grade self had known that this kind of flexibility and self-forgiveness was not only OK but wise.
I am left wondering, though, how many of our students hold tightly to rigid definitions of success and carry limiting narratives about who they are as learners? How might we help them rewrite those stories with courage and possibility? And how can I model self-talk that helps reframe failure as growth?
Radiating Joy
Like math, I had not studied Spanish in decades. Yet again, I was unprepared but was folded right into the fruit vocabulary review session. While I was excited to learn that “cranberry” means “bitter blueberry,” I found the fast-paced games even more thrilling. While playing Kahoot’s Submarine Squad, my heart raced as we shouted out answers, hoping to keep the sub afloat. We didn’t — but no one blamed me, even though I may have sunk the ship. Instead, they thanked me for playing.
The room was filled with laughter, energy, and lightness. And yet, joyfully, true learning was happening. Joy is an essential ingredient in our schools. It creates the conditions for risk-taking, connection, and engagement. Another question arose: How can we protect and prioritize joy, not only by playing games, and weave it throughout the school day?
Energizing Learning
As I returned to my adult roles, I carried with me more than geometry equations and fruit vocabulary. Grateful that I had carved out the day and protected it fiercely, I came back with a renewed commitment to presence. I listen differently now — to students, to teachers, to the spaces in between. I make more room for reflection, pause, and laughter throughout the day. And I’ve approached my leadership with greater clarity and curiosity.
To lead well, we must be willing to learn humbly. It’s easy to forget how effervescent, energizing, and vulnerable learning can be when we are consumed by responsibility. Stepping off the sidewalk — even for a single day — reminded me what it means to learn with an open heart and mind. And how much we ask of our students. And how much they offer in return, every day.
