“I went to the woods because I wished to live deliberately.” Henry David Thoreau
Last month, I wrote about intention. Before that, I talked about getting 1% better every day. But recently, I can’t shake a classroom visit that brought both of those perspectives to life in a way I honestly wasn’t expecting.
The last time I was in Miss Annie’s classroom was two years ago. This time, I popped into 11th-grade Honors English. The majority of my work is focused on listening and learning. Developing a collective vision, refining systems, and implementing strategy are central to that work. But trust is developed by staying closely connected to the people who translate that vision into reality.
I try to get into classrooms whenever I can. Not to evaluate but to see what’s happening. Twenty-six years ago, I taught in my own classroom. It’s a special kind of magic that unfolds within those four classroom walls. It gets me every time, watching a room where real learning is taking place. You can feel the energy as soon as you walk in. That’s purpose-driven work.
But this one just hit different.
Students were in the middle of a discussion about Thoreau’s Walden and Christopher McCandless from Into the Wild. The question in the room was a big one. When you look around at a world full of noise and pressure and people telling you who to be, do you run away from that? Or do you go looking for something better?
These kids are sixteen. And they were not giving easy answers.
One student argued that McCandless wasn’t running from anything. He graduated from Emory. He wasn’t flunking out like Holden Caulfield. He made a conscious choice.
Then another student pushed back right away. He said every single time McCandless talks about why he left, he only brings up what he can’t stand about society. He never talks about what he’s actually going after. “As I see it, that’s running away.”
Then a third student jumped in with this line about “killing the false being within.” Did I say these kids are sixteen? McCandless was scared of turning into his father, scared of becoming someone he couldn’t respect. And to land his point, he quoted, of all things, The Dark Knight. Yes, Batman. That Dark Knight. In the middle of a conversation about Thoreau. “You either die a hero or live long enough to become a villain.” I looked around to see if anyone was going to laugh. Nobody did. It worked!
I’m sitting there just really struck. It wasn’t just that their thinking was sharp. It was how they treated each other. A student would make a claim, then someone else would ask, “Where does it say that in the text?” They disagreed, but they didn’t dismiss. They actually listened to each other. Deeply. You don’t get that in a room where kids are worried about looking stupid. You get that when a teacher has put in the work, over months and years. That’s creating a space where you can think out loud and be wrong in front of your peers. If you remember being a teenager (I really hope you do), that’s no easy feat.
Miss Annie never once gave them an answer. Never let them off the hook. She had them stay there with their ideas. And she kept asking better questions.
At one point, a student started down a road toward nihilism, where Thoreau basically said that nothing matters, mostly because time is infinite and we’re small in a big world. As I watched Miss Annie, she gracefully slid into the class conversation and said something I keep playing on repeat. “Is he saying life is meaningless? Or is he saying life is too precious to waste on things that don’t matter?”
Silence. Not because they were confused. But because they were rethinking.
That right there, that’s teaching. Not delivering content and not keeping a classroom orderly in perfect little rows. That’s inquiry in action.
Thoreau wrote, “simplify, simplify, simplify.” Some think he meant do less. I don’t think so. He meant to be more deliberate, more intentional, about what you choose to do. That’s what I saw in Miss Annie’s room. She didn’t just throw a bunch of books at these kids. She built something across an entire semester. Catcher in the Rye. “The Ones Who Walk Away from Omelas.” Poems. Film. And now Thoreau. All of these pieces build an arc toward the most fundamental question. What does it actually mean to live with intention instead of just going through the motions?
One student connected a throughline in Thoreau’s critique of excess to our lives right now. We upgrade our phones every year. Nobody slows down. Another student said, and I wrote this down because it stopped me, “People live like ants. They work and die.” He’s sixteen years old.
I’ve been in a lot of classrooms. Twenty-six years’ worth, actually. I can tell when students are performing for me, and when they’ve forgotten there’s a visitor in the room. This was the latter. These kids forgot I was there. They weren’t trying to impress me. They were working through something real together.
And that’s what a great school does, isn’t it? It affords young people the chance to sit with hard questions. Hopefully, that school, that teacher, has figured out how to create the magic, those special conditions, that are cultivated and nurtured to have them figure it out alongside each other. Along the way, they pick up things no test could ever measure. How to build an argument with evidence. How to hold an idea you disagree with long enough, actually to understand it, and how to push back on someone without making them feel small, but showing respect and empathy. How to hear something that changes your mind. And admit it out loud.
Those are the factors that separate a student who walks across the stage from one who’s actually ready for what’s on the other side.
I walked out of that classroom and thought about something I try to remind myself of whenever the job gets loud. The most important work in a school doesn’t happen in a boardroom or a budget meeting. It happens in the space between a teacher and her students. Everything else, all of it, exists to protect that space.
My mother worked in an embroidery factory. She never had the chance to sit in a classroom like this one. But she gave me an important lesson that shaped how I see the world. She taught me to pay attention. To notice things other people walk past every minute of every day. The small things done right, that’s where dignity lives.
Miss Annie’s classroom was full of that.
Every time I visit a classroom, I learn something new. Sometimes small, sometimes big. But I always learn something. This time, what I took with me is that intention by itself is not enough. You can have all the best intentions in the world. But what makes it real is when a teacher shows up not only with intention but also adds depth and genuine care, all at once. Let’s do that every single day for kids who likely won’t even realize yet what we’re giving them, until some day they will.
That’s why everything matters.
With gratitude,
Superintendent of Schools
