As the youngest of four children and a lifer at The Wheeler School (’92) in Providence, RI, I grew up following in the footsteps of my older sisters and brother, and in the spring of 1983, all four of us were cast in the school production of “The Sound of Music.” My high-school aged sisters played the two female leads while my brother and I helped to round out the Von Trapp family lineup.
A third-grader, I was the youngest student to be cast in the play, and I played Gretl, the youngest Von Trapp. I loved going to rehearsals, waiting for my two minutes on stage while watching scenes from the wings.
My oldest sister was great at being someone she wasn’t, a conniving baroness. My other sister was a perfectly innocent Leisl, singing about being 16 going on 17. My brother was a charming, mischievous Kurt. In real life, at our house, none of us acted the way we were directed to on stage. But at school, we were able to try on other personas and use our voices in new ways.
Jessica (l.) and her siblings in "The Sound of Music" at The Wheeler School (1983). Photos courtesy of Jessica Flaxman
Pausing at a Crossroad
Then, while I was in the dressing room backstage one evening and listening to the chatter of cast members getting into costume, I heard one girl say to another, “It’s called ‘The Sound of Music’ but it’s more like the Sound of Flaxman. It’s like it’s their school.” Her words confused and upset me. What did she mean? How was school our school? I didn’t know. But I suddenly wanted to pull away from them. To be a little more independent. A little less connected. A lot more free.
I never went out for another all-school play. When I saw my sisters or brother in the courtyard, I gave them a quick glance or a hug before running off with my friends. Once my sisters and brother graduated, I felt more independent at school. My high school years were blessedly sibling-free. But they weren’t as much fun. I realized, as I approached my own graduation, that what had made my elementary school experience so fulfilling was, in part, my connections with those who had come before me.
Getting in Line
I learned more about the fine balance independent schools play in fostering individual voice while nurturing lasting connections when I became a teaching fellow at Phillips Academy Andover (MA) in 1997. That was the year I found my calling and my career. Just as I had seen and felt at Wheeler, the place that had nudged me toward independent thinking while encouraging me to contribute to the greater whole, Andover did the same for its faculty.
Thrust to the front of the class for the first time, I was never really on my own. I was a part of two cohorts: the teaching fellows, all of whom were young and inexperienced, and the English department’s seasoned faculty members, who were always willing to listen to ideas, give feedback, and offer lessons and activities I never could have dreamed up on my own. I was happily dependent on all these teachers, and they were somehow also dependent on me.
That interdependency, that connection between and among us, was at the heart of everything we did and enjoyed. It transcended the dining hall, the playing fields, and the walls of the classrooms.
Taking a Road Less Traveled
When the fellowship ended, I seized the chance to be a part of a brand new high school. Bentley Upper School (CA) opened its doors to the first class of freshmen in 1998, and I was there to greet them. But again, I wasn’t alone.
Working with an experienced English teacher from Phillips Exeter Academy (NH), I was pushed to think about what an English department needed to do and be for students at the turn of the millennium. We also grappled with what it meant to be part of a school community without a long-standing legacy. As we laid the foundation of Bentley Upper School’s future, I began to grasp a simple, yet profound truth: The ties that bind an independent school together — the very ties that bound me to my siblings and to The Wheeler School — are its most priceless assets.
After a year in California, I headed back to the northeast with my law-school bound fiancé, this time to teach at Collegiate School in New York. I worried about how I would fit into a community that had been serving boys and young men for centuries. But I knew I wanted to continue being a part of an independent school and to understand what makes all independent schools both unique and familiar. In this experience, I sought to be present with the thoughts and performances of others. To be in the cast, to work the backstage, to sit in the audience, to applaud and be applauded.
My department chair at Collegiate left a mark on me about what independence — in fact what leadership — really looks like within an independent school. As our department leader, she modeled excellence in lesson planning, shared her lessons freely, and enthusiastically adapted her plans around better ideas she solicited from teachers and students alike. She expressed views on behalf of herself, her faculty, and her students in every meeting and venue. She was beloved by the boys, men, and women she served and inspired, and she reciprocated that care for each of us. She was completely connected to us, and that connection helped her to lead.
Stepping to the Front and Bringing up the Rear
It was the intersection of becoming an independent school parent and joining the faculty at Charlotte Country Day School (NC) that ushered me into the next phase of my own independent school journey, administration. Over the course of a decade in the English classroom with upper school students and their siblings, and then as department chair and director of studies, time and again, I benefited from the thoughtful direction and choreography of those around me.
Although I was in an increasingly independent position, at no time was I alone in my work. Whether choosing a theme for summer reading, adjusting the honor roll threshold, introducing a new class, shifting a teaching team, or building an all-school digital citizenship program, I needed and had the support of others.
At the same time, on a parallel stage, my daughter was experiencing that same beautiful journey of working with others to become more herself. Whether on stage with 125 of her kindergarten classmates, or presenting a research topic, a few years later, with her fourth-grade peers, my daughter’s experience in the school mirrored my own as a child. Our twin journeys highlight the power of independent schools to strengthen individual voices while celebrating shared achievements.
Jessica's daughter in her third-grade play (2010).
Independent: Connected and Free
I haven’t performed in a play in years. I’m no longer a student or a classroom teacher. This past summer, I stepped into a new challenge, leading the all girls’ middle school at Nashoba Brooks (MA).
On the face of things, I am more independent than I ever thought I would be. But I am in no way alone. In my work as a division leader today, I know I can’t do what I do without the creativity, effort, and goodwill of others. Without the ensemble that gathers each morning at school, there can be no show.
I still hear that voice from 1983. I want to say to her, the play was yours as much as it was ours or mine. Each of us is integral to the school to which we belong, in which we play a part, and it is through our connection that we find freedom.