When I learned I had been named the 2022 Vermont Principal of the Year, I truly believed they had the wrong person. In the exact moment that I got word of the award, four of our most disenfranchised learners—who were asked to leave the cafeteria many times after being disruptive—were seated next to me in my small, windowless office. They had simply adopted my office as a safe place to eat lunch and be themselves. I didn’t see the harm in letting them do so. They were respectful to me, and respectful of the space, even when I wasn’t there.

This day, they were engaging in what appeared to be a raucous and raunchy conversation about the previous weekend. I had walked away to check in on another student and returned to find a teacher standing in the hall in disbelief, yelling “How dare those words come out of the principal’s office of all places!” While the kids’ conversation continued and exceeded even my tolerant standards for teenage existence, the call came notifying me of the award. When I learned I had been selected for this honor, all I could think of was my complete feeling of failure at that moment. How could I possibly be recognized by colleagues and peers for doing something … anything … right, while students who were sitting right in front of me felt like they had no home in the school I was responsible for? Control of the school environment felt like it was quite literally collapsing around me, and every attempt to get it back in line was thwarted by the promise of yet another day of 15 staff absences.

Talking to people then and now, I don’t believe I’m alone in that feeling. And that is why it’s so important to celebrate ourselves—school leaders who have not only persevered but found ways to still shine through the last two and a half years. We all have partners, parents, and friends who have walked with us through this journey and who deserve our gratitude. This year, during National Principals Month, let’s certainly remember to thank them but also recognize that we alone know the walk we’ve walked.

Rising to the Challenge

Every single school leader in this country has experienced a set of circumstances that the world around us will never understand. I do not know of a single person who has prepared for their current role through combined previous experience as an epidemiologist, criminal justice expert, police officer, public relations consultant, mental health counselor, grief counselor, expert in graduate level racial theory, school nurse, and psychic capable of predicting the future, but that’s exactly what we were asked to do for the last couple years, while also serving as full-time contact tracers. On top of it all, we were expected to have the conflict resolution skills of international diplomats at one of the most polarized times in our nation’s history, with schools at the very center of seemingly every controversy.

Think about the very beginning of the pandemic. When we were attempting to help our communities make sense of the world turned upside down and our state departments of education gave us a homework assignment to reimagine schools overnight—making sure to justify exactly how we were going to meet a plethora of continued quality standards, demonstrate excellence at working around longstanding broadband and infrastructure problems in our rural areas (and do so during a time in which we weren’t even sure if we were allowed to drive to the grocery store)—school leaders rose to the challenge, and we haven’t stopped innovating and adapting since.

Once we just about got the hang of existing remotely, we were faced with the effects of that remote existence on our students, in which their phones, and in far too many cases, addictive substances, became their only source of social connection and school was practically optional. How many times have we heard someone complaining that “Students are out of control, and nobody is doing anything about it!” after devoting hours or days of our time to making sure a student gets what they need to stay alive, let alone be happy and feel centered. For me, our profession is an uphill climb that few people who are not walking in our shoes will ever fully understand.

And here we are. I believe our greatest gift in this moment is a blank canvas, and the realization that we don’t have to go back to normal if normal wasn’t working so well anyway. Last year, we were not so eagerly awaiting the next guidance document that would prescribe the first few months of the school year. This year, in all corners of the state and elsewhere across the country, the theme seems to be building it back ourselves. I know I’ve become so torn between so many different levels of problem-solving and trying to figure out “what’s right,” that sometimes I lose sight of what’s actually working.

Those kids swearing in my office last year had simply found a place where they were trusted, respected, and free. They needed that. We all need to build on moments that truly matter. For me, those moments include accompanying a student on the bus and handing him my old cellphone in case he needs to call 911, knowing that child protective services hasn’t yet been able to keep him out of an unsafe environment, and he has no other choice but to go home, and make sure to appear in court when he finally has the opportunity to tell his story.

It’s allowing a student who has dropped out for two years to come back, putting the tools to graduate back in her hands, and being moved to tears when she unexpectedly pulls out a trumpet from under her seat and plays along with the band as she walks out of the building for the last time.

It’s passionately advocating for a student who has spent the last three months trying to burn bridges with every adult in the school, because unfortunately the bridge his parents burned first with him was permanent, and we were all he had left.

It’s networking like crazy behind the scenes, connecting community members with a student whose powerful voice and impeccable research skills enabled them all to work together to finally replace our previous mascot (the Indians) with one that would not cause harm. As a side note, I want to echo advice I received a few years ago: If your school is going through a change that needs to happen, make it happen fast, and you’ll be amazed at how quickly the dust (usually) settles.

At our school, not a single current student ended up raising their voice in opposition to changing the mascot. They leaned into becoming “the Danville Bears,” relieved that they finally had something they could go all out with. One of our most conservative high school students explained it this way: “I don’t quite see why it had to go, which is just my opinion, but more importantly, I really hope I don’t care about high school so much as some of these alumni when I’m 50. We just want to cheer for something. This is our school and our time. They had theirs.” The kids know what’s up.

Digging Deep Into Who We Are

The author Parker Palmer reminds us that the students we teach are larger than life and even more complex. He tells us that, to see them clearly and see them whole, and respond to them wisely in the moment, requires a fusion of Freud and Solomon that few of us ever achieve.

I would argue that the tools to try to see them clearly and respond to them wisely means digging deep, not only into our own well of limitless patience for problem-solving, but into the true core of who we are. One afternoon this summer, seeking inspiration, I drove a couple of hours south and took a walk along a boardwalk I helped build in 2006, where the Appalachian Trail crosses the Ottauquechee floodplain near Killington, VT. Joining a fall trail crew and learning carpentry skills in the woods was one of the most formative moments in my professional life. Real-world outcomes, the ability to take risks, working with others, and facing challenges with clear criteria for success defined the experience to the point where now, 17 years later, it’s still exciting to identify individual boards that I placed and areas where I could see how my skill developed along the way.

This year I’m in a new role at my school, supporting our learners who do not follow the traditional pathway and need a more hands-on approach. Seeing this crucial student need, I reached back to my core as an educator, and as a human, and realized I could be more effective doing this job myself, rather than hiring someone to attempt to replicate my own skills. It came with a small pay cut, but it’s well worth it to be able to lead in this role. To be successful, I will draw on the power of experiences like the trail crew, as well as lessons learned from leadership through extraordinary times. And so, whatever truly drove you to be the person you are, let that inspire your work as a school leader this year. Seek justice, speak your truth, and walk alongside your students; they need you now more than ever.


David Schilling is the technical and experiential learning director and the former principal of Danville School in Danville, VT. He is also the 2022 Vermont Principal of the Year.