On the Road

I’ve worked in independent schools for 14 years — first at a boarding school, then a day school, then a boarding school again. While there are many similarities between the two school types, I was reminded of some key differences when I joined Cheshire Academy in August of 2018.

For one, boarding schools operate around the clock — 24 hours a day and seven days a week. That’s not to say that life at a day school ends as soon as the final bell rings, but it’s a different dynamic when students are living, eating and sleeping on campus.

In my first few years, I focused on my business office duties, rarely getting involved with the hustle and bustle of student life. In those days, students were merely faces in the dining hall or names on a spreadsheet. So when I was asked to join the “weekend duty” team two years ago, I initially balked at the question. I was used to working more than 40 hours per week, but this seemed like too much.

For those unfamiliar, weekend duty refers to the responsibility of supervising and engaging with boarding students during off hours. In the early part of the year, this helps the students adapt to life on campus more quickly, and, hopefully, prevents or at least eases any homesickness. During the remainder of the year, it’s still important that we provide weekend activity options so that the students can stay active and, with any luck, stay out of trouble. From the administrators’ perspective, weekend duty should give us a better sense of what goes on in the school community.

Despite my initial reservations, something compelled me to dive right in. My first weekend duty assignment was to cover open gym on a Friday evening. Truth be told, I mostly spent the time scrolling through emails on my phone and walking around the gym every so often to make sure no one was getting into trouble. I was certain that there were no teenagers that wanted to hang out with a middle-aged guy like me in their free time.

Since then, I’ve tried to be more involved by running on the treadmill and using some of the Nautilus machines. I don’t run as many miles or lift as many pounds as many of our students, but it’s one way that I can feel more connected to the school community.

One of my regular weekend duties involves driving a toaster bus or minivan to transport students, whether to a sporting event or a trip to the mall. It’s amazing how well you can get to know a student just by chatting with them during a drive, even if the conversations are sporadic.

Many of our faculty, understandably, don’t prefer this assignment, but I don’t mind it. I just pack plenty of snacks and drinks, both for myself and for the students, so I’m prepared if the drive goes longer than expected.

One driving assignment I often take on is transporting our international students to John F. Kennedy International Airport in New York City for their flights home during winter, spring or summer break, as well as picking them up upon their return. The drive takes about two hours without traffic, although I don’t think I’ve ever driven in or near New York City when there wasn’t traffic. Many of our faculty, understandably, don’t prefer this assignment, but I don’t mind it. I just pack plenty of snacks and drinks, both for myself and for the students, so I’m prepared if the drive goes longer than expected. To me, it’s a good distraction from my usual world of debits and credits, insurance claims and legal matters.

Another area where I sometimes pitch in is covering classes when a faculty member is out sick or at a conference. While I’m not expected to actually teach the class, I go beyond just taking attendance and making sure the students work on their assignments. When possible, I try to walk around the classroom and see what conversations I can strike up with the students.

Despite all this effort, I still wasn’t sure that I was truly connecting with the students until one day last spring. That morning, a student walked into my office unannounced, excited to tell me that she was accepted into the same university that I attended. I knew that she was applying, but I didn’t realize that she remembered me — let alone knew where my office was, as it is not very close to our academic spaces. This moment gave me more job satisfaction than I’ve ever gotten from balancing a bank statement or preparing a financial report. It was a great reminder of why we do what we do.