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Head of School Reflection — New Year’s Letter to Past, Present, and Future Boarding School Educators

Head of School Reflection — New Year’s Letter to Past, Present, and Future Boarding School Educators

With the 2023-24 hiring season underway, I can’t help but contemplate my inaugural boarding school interview process during my final semester of college in 1994.  The colossal conference meeting room at a hotel in Boston.  Eagerly awaiting the arrival of notes in candidate mailboxes inviting us to an interview, which then inspired us to madly look through massive books that chronicled independent schools demographically.  From there, I found myself on the campuses of Blair Academy, Shady Side Academy, Tilton School, and Deerfield Academy, ultimately landing in Blairstown, New Jersey, for what has become a 29-year boarding school journey.  I could not imagine then that what began as a gap year before medical school would quickly become a career and lifestyle of purpose, community, and deep relationships.

Fast forward to the years leading up to the spring of 2020, and many boarding school leaders were in heated debate regarding the value proposition of a boarding school education.  As more academic courses and experiences were offered virtually, would the demand shrink for small, in-person classes?  With practically unlimited access to a broad and deep range of online curricular offerings, how could our communities that also carve out intentional time for athletics, arts, residential programming, and student activities compete with the reality that teenagers could now immerse themselves in multivariable calculus or intensive foreign language taught by a college professor?

And then the world was disrupted by a pandemic.  We reacted, recentered, endured, and steadily moved forward with two indisputable truths:

1) With rare exception, the paragon academic and learning experience is in-person and relationship-based.  

2) Teenagers are best positioned to navigate adolescence with a team of adults in their corner.

Regarding the first, while classes taught via Zoom were a saving grace in the spring of 2020 and beyond, even the most talented and determined teachers struggled to maintain a high level of student engagement remotely.  Many students realized that the academic expectations normed within a physical classroom had been instrumental to their performance, and the lack of social interactions made learning less compelling.  These are broad generalizations, of course, but they stem from myriad conversations and observations I experienced as a head of school, colleague, and parent.

Regarding the second, we knew that the experience of adolescents is buoyed by adult connections in their lives long before COVID and could point to countless examples of where those “teams” exist, from recreational sports and faith communities to extended families and all types of schools in every town, city, and state.  That said, the lack of these connections during the pandemic boldly affirmed this knowledge.  And in boarding schools specifically, our infrastructure is designed for parents/guardians to “join forces” with faculty who serve as advisors, coaches, teachers, and mentors and for students to find equal parts reassurance and self-reliance within this framework.  Being in our students’ corner is a timeless drumbeat of boarding schools.

My goal in reaching out to past, present, and future colleagues, then, is to acknowledge and address a growing concern that our industry has continued to approach the recruitment and retention of those very student-centered adults much as we did in 1994.  Therefore, I am asking for the collective help of veteran and mid-career boarding school educators as well as the consideration of those on the cusp of your journey as educators.  Here we go.

Ten years ago, I offered a presentation during a TABS conference that applied Daniel Pink’s Drive theory of intrinsic motivation (autonomy, mastery, and purpose) to the opportunities provided by a career as a boarding school teacher.  By definition, independent schools allow for a degree of autonomy (across curriculum, programming, and departments) and create avenues of professional development, mentoring, and collaboration that lead to mastery.  

The purpose inherent in our shared work rarely needs explaining.  In this new year, however, I believe there could not be a more compelling time to focus one’s professional career on the lives of teenagers.  Our role in helping to set students on a path forward is undeniable.  And the world of 2023 is one in desperate need of young people with a strong moral compass, an appreciation for collaborative problem-solving, and an understanding that they are our best hope to solve—rather than be suffocated by—the many and complex problems this world faces.  Purpose is the very calling of boarding school educators.

One caveat: Working and living in a boarding school campus is not for everyone, and I believe we need to be more direct and honest about this reality.  Gone are the days when being a bright, accomplished, and hardworking college graduate—who has spent a few summers as a camp counselor—was a ticket to success as a teacher, coach, advisor, and dorm parent.  Indeed, those attributes provide a critical foundation, but as the expectations from students and parents rise exponentially regarding faculty experience, expertise, communication, and attentiveness, we must acknowledge that the work grows more challenging, even as it remains interesting and rewarding.  Moreover, we must continue to bolster our rookie, mid-career, and veteran educators with collegial support, opportunities to develop autonomy, mastery, and purpose, and time for rejuvenation.  And, as Daniel Pink will remind us, intrinsic motivation and a deep sense of engagement in one’s work stem from a healthy baseline of compensation and benefits, key factors the leaders of our industry are taking to heart and considering in more creative and proactive ways. 

No, this isn’t a job for everyone.  But for those who fall in love with the pace and pattern of a school day, week, and year; with the personal and professional benefits of living in a community that manifests the “it takes a village” proverb; with the full range of individual/family life chapters supported by a boarding school career*; and with student growth, community traditions, and moments of joy and affirmation woven throughout, there truly is no better job.

Which brings me back to my ask.  We are all well aware that the current workforce has choices and opportunities that certainly did not exist five years ago, let alone in 1994.  Remote/hybrid work, persistent shopping for new employment, and a “casual” approach to loyalty to one’s job do not play in our favor.  And yet!  The choices and opportunities we have as boarding school educators deserve fresh branding and widespread marketing.  

Experienced boarding school educators: Let us continue to model for and mentor to the next generation.  In 1994 my science department chair reviewed my assessments and vetted my approach to grading but also taught me how to inspire conversation among students during family-style meals, to offer feedback to colleagues, and to “grow up” as a young professional.  I am eternally grateful for the many, many mentors who provided equal doses of affirmation and constructive criticism, who opened doors for me and had my back along the way, and who persistently offered honest perspective on the benefits of sticking with boarding school.  This is our shared responsibility that comes now with a sense of urgency.  My ask to you, then, is to help grow, fortify, and promote the avenues by which teachers consider and commit to boarding school as a career.

Those considering a career as a boarding school educator: You will build relationships with colleagues of all ages that fundamentally (and positively) impact you as a teacher, role model, and community member.  You will help bright-eyed, complicated, earnest young adults from across the country and around the world prepare for everything from their first athletic contest and theater performance, to their first college interview or first job, and everything in between and beyond.  Your students will carry your voice and values forward as they develop their own.  And many will stay in touch for years, if not decades, to follow.  It will not be easy, but on balance, you will find the work rewarding and energizing.  My ask to you, then, is to take a close look at the differentiating aspects/benefits of teaching in a boarding school in order to appreciate and consider this unique, purposeful, and compelling life’s work.

This fall, I had the privilege of welcoming one of my former students to Canterbury’s campus to speak with our students.  Now a successful professional with a doctorate—and a parent of two—she has become a colleague and at times a mentor to me.  This connection will be lifelong, ever-evolving, deeply meaningful, and a constant reminder of how fortunate we are to play a role on those very teams of adults, setting our students on a course forward.

Please join me in this new year to reaffirm the good work we do as an industry and to rebuild the avenues by which our colleagues become and remain boarding school educators.  I encourage heads of school and their leadership teams, search/placement firms, boarding school parents and alumni, and rookie-to-veteran colleagues across boarding schools to join this conversation within and beyond our communities.  We can no longer take for granted that the opportunities woven throughout our careers as faculty members—teachers defined in the broadest, deepest, and most wonderfully impactful way—are well understood.  As I continue to seek ways to draw greater attention and commitment to this career and lifestyle of purpose, community, and deep relationships, I invite you to do so as well.

With gratitude,

Rachel Stone P '23, '24
Head of School


* I do not know of other careers that truly support and develop employees across both their personal and professional “life cycles.”  Each school year comes with opportunities to teach new courses; collaborate with colleagues within/across academic disciplines; coach new sports and direct new plays; develop new student activities, affinity groups, or travel experiences; and deepen expertise and leadership along the way.  Summers allow for travel, professional development, alternative work experiences, and/or time with family.  The community structure welcomes single faculty, couples, families, and everything in between, and while every boarding school approaches faculty housing in its own way, each institution values the unique and powerful modeling of lived values our students experience by navigating adolescence in the presence of faculty.  “It takes a village,” indeed.


Head of School Reflection — New Year’s Letter to Past, Present, and Future Boarding School Educators