Every Monday evening, I pile into a school van with anywhere from eight to twelve Franklin Academy swimmers and head to a nearby high school for practice. On the surface, it looks like a simple logistical task. Get students to the pool, coach the workout, bring everyone back safely.
But over time, these Monday van rides have become something much more meaningful. In many ways, they mirror a familiar ritual for families everywhere: the conversations that happen in the car on the way to and from school activities. Anyone who has driven a teenager knows that the car can become one of the most honest and revealing places to talk.
Originally, I volunteered to coach swimming because I wanted to reconnect with my own competitive swimming background. I love being on deck. I love writing sets, watching athletes push themselves, and helping students discover that they are capable of more than they thought. But what I did not anticipate was how much I would come to cherish the time in the van.
Those rides have become one of the most authentic windows into student life.
The conversations are wide ranging and wonderfully unpredictable. One week, students might debate what improvements they would love to see around campus. Another ride might turn into a brainstorming session about what should be sold in the school store. Occasionally the topics are more reflective, like talking through college applications, weighing future goals, or navigating the stress of a decision letter.
And sometimes the conversations are simply ridiculous in the best possible way.
One ride turned into a philosophical discussion about what alternate lives we might choose if we could start over somewhere else. Another ended with the entire van laughing as one student created a playlist of what they declared to be the worst songs ever written. The laughter lasted the entire trip.
In those moments, I see a side of our students that formal settings rarely capture. The humor. The creativity. The candid honesty.
There is another benefit to these rides that I value deeply as Head of School. In the van, the hierarchy of school leadership softens. Students speak freely. They share opinions about programs, facilities, schedules, and everyday life at Franklin. It is unfiltered feedback that gives me a real pulse of campus.
Sometimes that feedback leads directly to change. Sometimes it simply gives me a clearer understanding of what matters most to our students.
At the same time, the van becomes a place for mentorship. I might help a student think through an academic plan, talk about managing stress, or discuss college choices. At times I become a sounding board for practicing mindfulness or reframing a difficult day.
Other times, I am simply the driver while the students roast me about how old I am getting.
Sarcasm is the dominant language of the van.
And honestly, I would not have it any other way.
Boarding schools often talk about the holistic nature of education, and these van rides capture that idea perfectly. In a single trip, we shift between coach, advisor, college counselor, listener, and sometimes comedian. We talk about academics, athletics, friendships, the future, and whatever random idea pops into someone’s mind.
It is education in its most human form.
Most importantly, these moments remind me why boarding communities are so special. The relationships extend beyond classrooms and offices. Learning happens in informal spaces, during shared experiences, and in conversations that unfold organically.
My favorite part of the Monday van rides is simple. At Franklin Academy we use first names, but students still know my role. In the van, though, that title fades into the background.
For those forty minutes on the road, I am not the Head of School.
I am just Alex.
And that might be the greatest benefit of boarding of all.
