Head of School’s Notebook: Where the World Feels Simple Again
September 12, 2025
Reflections from Outings Week
Jesse Morrison, Assistant Athletic Director for Program, was my pod co-lead!
After a flurry of activity to get the year launched, the Mesa fell quiet as we ventured into the wilderness for our annual Outings Week. In a world where breaking away from our phones and a fast-paced routine is rare, Cate’s unwavering commitment to the distinct educational opportunity that only the backcountry can provide is exemplary.
This is my third year participating as a leader – my first at Pyles and the past two as a Kern guide for Juniors. While our freshmen and juniors camped merely 40 miles apart—separated by a few mountain passes and the rushing Kern River—the developmental distance between these grades feels immense.
Our 9th graders are forming new connections at Pyles, learning what it means to care for themselves while nurturing our core value of companionship. Meanwhile, the juniors I led into the wilderness are stepping into their full potential, taking on the physical challenge of hiking 45 miles while discovering what it means to lead their peers and allowing the natural world to reset their minds, bodies, and spirits.
It’s in this backcountry where the world feels simple again. Here, life distills to its essence: the importance of the next step, the pause to take in a breathtaking view, the encouraging words offered to a struggling friend. Disconnected from technology and carrying only what they need, our students rediscover what truly matters.
This simplicity revealed itself most powerfully on our final day when our group decided to tackle our biggest challenge: a 14-mile uphill push. Rather than feeling burdened, my 13 juniors became supercharged. They spent hours singing, offered to redistribute pack weight during challenging stretches, and marveled at how much stronger they’d become in just five days. The day grew even more epic when we took a wrong turn at the midpoint. Instead of backtracking, we chose a new route—one that added four additional miles and carried us over an 11,400-foot pass.
As both the leader of this school and this expedition, I constantly navigate the delicate balance between pushing our community to discover new dimensions of our potential while remaining vigilant of individual and collective well-being. My vision for transformative education rests upon a dual commitment to “doing well while being well”—and this trip embodied that philosophy perfectly.
My favorite moment came when we emerged into Big Whitney Meadow, part of our unplanned route. Over and over, the refrain echoed: “I am so glad we made a wrong turn—look where we are now, it’s magical. I didn’t think I could do this, and yet, I feel strong.” In that meadow, surrounded by peaks and possibility, we discovered something better than we could have ever imagined in and beyond ourselves.
As we embark on this new school year with all our carefully planned routes mapped out, I find myself hoping we’ll lose our way again. Sometimes the most profound learning happens not when we follow the prescribed path, but when we trust ourselves enough to venture into the unknown and discover the magic that awaits. And, if you find yourself feeling lost along the way, may you always remember that you’re never alone.
