The First Lesson

When I visited campus as Proctor’s Head of School-Elect last winter, I asked a group of Proctor students what experiences I needed to have if I wanted to truly understand the culture of this place. They didn’t hesitate: Wilderness Orientation.  

I’ve always loved the outdoors. I grew up going on canoe trips and later became a trip leader myself, but always with a paddle in my hands. Hiking? Only day hikes for me. Never had I packed everything into a backpack and carried it for five days. My biggest fear was toppling over with my pack, stuck like a turtle on its back.

At Proctor, we believe so strongly in the power of Wilderness Orientation that it is a graduation requirement. Five days and four nights in the woods, in groups of six to eight students with two adult leaders. The purpose of Orientation is bigger than the mountains we climb, however. It is about knowing Proctor deeply from the very start. It is experiential learning at its best, collaborating, building relationships, leaning on each other, discovering what we can do together, and unearthing the courage inside ourselves.

I am deeply grateful to the students in my group. Their energy was contagious from the moment we met, and as soon as we were on the trail, they fell into easy conversation, laughing and sharing stories. They took responsibility for everything: planning and cooking meals, cleaning up, checking the map, hauling the bear hang each night, and filling water bottles. They did it all while encouraging one another and making sure everyone felt included. Sarah Wood Doherty ’03, Alicia Barry ’15, and I quickly realized that our role as trip leaders was to step back and let the group discover how to trust and support one another.

Five days completely unplugged and sleeping under the stars reminded me that growth happens when we step into the unknown. Our students arrive nervous, uncertain, and unsure what to expect. They return stronger, more confident, and more aware of who they are and who they want to become at Proctor. They come back with a group of friends before they even set foot in a classroom. 

I carried a journal for the students to write and draw in, hoping it might become a tradition, passed from trip to trip during my time at Proctor. The entries reflected on hikes and meals, but what shone through most clearly was the power of the experience. Finley ’28, who had to leave her Orientation trip early last fall due to an injury, returned last week, determined to finish what she had started. She wrote:

“Proctor is special. It is a place to call home with people to call family. Amy uses the word community a lot, but I believe family fits better. Proctor brings out a version of me I never thought I would be. Remember, be yourself and keep smiling. Because that is all you need at Proctor.”

Finley’s wisdom as a fifteen year old captures more than I could ever write in this piece. So often, our students can become our guides (as adults) if we simply create the space for them to lead and be themselves. In fact, Finley’s words may become my own motto for Proctor: be yourself and keep smiling, because that is all you need at Proctor.

What a perfect first lesson.

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