The Head of School – October 15, 2025

Flint Hill Community,

Last week, I had the joy of joining our Director of Alumni Relations on a road trip to Boston and New York City to connect with our alumni community. These visits are always among my favorite parts of the year — an opportunity to see how our graduates are continuing to learn, lead, and live out the values that began here at Flint Hill.

In Boston, we hosted a college-aged alumni dinner that brought together twenty current Huskies now studying at Boston College, Boston University, Northeastern, MIT, Harvard, Tufts, and WPI. The conversation around the table was inspiring — filled with stories of new independence, challenges, and discovery. Many shared how their Flint Hill experience prepared them not only academically, but socially and personally: knowing how to advocate for themselves, build relationships with professors, and seek out leadership roles as interns, researchers, and innovators on campus.

The next night, we gathered in New York City for our New York Alumni Reception, where graduates spanning nearly three decades — from the Class of 1998 to recent alumni — came together for an evening of connection and celebration. Some traveled hours to attend, including one who drove in from Upstate New York and another who took the train from New Haven just to join in. The group reflected the wide range of careers our alumni pursue: venture capitalists, human resources directors, professional sports management, doctors, lawyers, engineers, educators, and entrepreneurs. Many also expressed a desire to “pay it forward” — offering mentorship, internships, and connections for current students and recent graduates.

As educators, we naturally focus on the student experience here and now — the lessons, relationships, and opportunities unfolding each day on campus. But gatherings like these are a reminder that, at Flint Hill, we are also playing the long game. The foundation we build together helps our students not only succeed at college, but thrive throughout their lives. And, as many alumni shared, it’s often the challenges they experienced as Flint Hill students — the tough teacher, the demanding project, or the personal setback — that they now look back on as instrumental to their resilience and success today.

Whether your child is preparing to graduate this spring or that day still feels many years away, please know that our commitment remains steadfast: to nurture every Husky’s growth, equip them for academic and personal success beyond Flint Hill, and celebrate the remarkable individuals they become.