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Placed carefully among the old photographs, well-worn books, and school memorabilia you might expect to find in the office of a man who has dedicated his life to education, is a simple wooden sign inscribed with the words “It takes a village.”

The Village is what first attracted Tim and his wife, Anne, a partner in every sense of the word, to Pomfret. “It was the people who brought us here, and it is the people who have kept us here,” Anne says.

At the same time, Tim understood that the world was changing, and he told the trustees who hired him that Pomfret would need to change with it. “We are a more nimble school than we were in 2011 — more adept at and accustomed to change. If that turns out to be my legacy, I am okay with that.”

In June, Tim and Anne said goodbye to fourteen remarkable years at Pomfret, and forty incredible years in education. And while they remain humbled to lead this place they love so much, they are ready for a new adventure.

“I have always believed in the value of change, and that is true for school leadership as well,” Tim says. “We’re leaving because it’s time — and because we believe deeply in the team that will carry this work forward.”

THE WAY TIM TELLS THE STORY, it was love at first sight. The way Anne tells it, not so much.

The pair first met during freshman orientation at Connecticut College in 1981. “I saw her from across the room and I was struck,” he remembers, a small crack appearing in his otherwise steady voice. Not long afterward, he told Anne that one day they would be married. “I remember laughing it off at the time,” Anne says with a smile. Tim and Anne got married in 1989 and have been married for the last thirty-six years.

Even then, the two had a lot in common. Tim and Anne both came from families with deep roots in education. Anne grew up in Harvard housing, the daughter of a Harvard professor. Tim was a faculty brat who spent his youth traipsing around Phillips Andover Academy.

“We only knew the world of education,” Tim says. “I’m a fourth-generation teacher. Both my grandfathers were educators, my great grandfather was an educator, my parents were educators. It’s kind of a strange way to grow up, but that’s how I grew up, how my parents grew up, and how our kids grew up.”

At Connecticut College, Tim was a French and psychology double major, and for a while, he thought he might become an organizational psychologist. “Anything but teaching,” the eighteen-year-old famously and emphatically declared when he was asked about his career aspirations. Then, in the summer of 1984, just before his senior year of college, Tim accepted a job as a teaching assistant at the Andover Summer Session.

“The head is important, but so too is the heart,” he says. “And sometimes the heart knows in an instant what it can take years for the head to understand.”

After three years at two other schools, in 1988, Tim was offered a teaching job at St. George’s School in Middletown, Rhode Island. At St. George’s, Tim and Anne settled into boarding life. They lived in the dorms and hosted advisory dinners. Tim taught French and psychology, and coached squash and football. Anne got a job teaching fourth grade just down the road at St. Michael’s Country Day School.

After a few years, they had their first child, a boy named Max. Then came Molly. And finally, Lucy. They spent summers at Squam Lake, nestled in the foothills of New Hampshire’s White Mountains.

One of the gifts of their tenure at St. George’s was the opportunity to raise their children in a school community. “Our kids were surrounded by mentors, teachers, and friends who knew and loved them,” Anne says. “They got to see their parents doing work that mattered.”

In 1997, Tim was named dean of students. A few years later, he became assistant head of school. Before they knew it, twenty-three years had flown by. About a year before the head of school opening at Pomfret became available, Tim remembers Anne giving him the nudge he needed. “Is this what you want to do for the rest of your life?” she had asked. He thought about it for a while, and then replied, “No, I think I have something more to offer.”

TIM’S FIRST FORMAL ACT as Pomfret’s twelfth head of school was to delay the opening by a week. “Right before we were supposed to start school, a massive storm hit campus and we didn’t have generators,” he remembers. “We didn’t have power, couldn’t refrigerate food — welcome to the world of making big decisions.” 

Tim describes his first year as an intensive crash course in “How to Become a Head of School,” with extensive travel to places like Asia, and a focus on getting to know the community, especially the Board of Trustees. “I had been exposed to these things as an assistant head at St. George’s, but actually being the head was a whole different level of challenge and responsibility.” 

Their daughter, Lucy, who was entering Pomfret as a freshman, helped Tim and Anne find their footing. “The first year was really good for both of us,” Anne says. “Having Lucy as a freshman allowed us to put down roots right away.” 

Not long after his arrival, Tim began outlining a new and bold approach to teaching and learning that would eventually become Pomfret’s 2013 strategic plan, The Pomfret Purpose. “Historically, education happened in a very individualized fashion,” Tim says. “The teacher dispensed information, and it was the job of the student to retain and then parrot back what the teacher had said.” 

“What I wanted to do was make the teaching and learning happening inside the classroom look and feel more like the work happening in the world outside of the classroom. At a fundamental level, I wanted to put student agency front and center.” 

It was a promising vision, but one without a clear path forward. Then, in the summer of 2013, Tim took a long bike ride with the man who had hired him. Peter Grauer P ’02, ’10 had stepped down from being board chair a year earlier, but he and Tim had stayed in touch. During the bike ride, Grauer asked, “So, what do you need to get your vision off the ground?” 

Tim said he needed a “campus resource” — it didn’t have a name yet — run by someone with the expertise, energy, and drive it would take to operationalize the boldest parts of the strategic plan. Not long after that conversation, Peter and Laurie Grauer offered to fund the creation of a new academic center: The Grauer Family Institute for Excellence and Innovation in Education. 

Since its establishment in 2013, the Grauer Institute has led to a slew of cascading improvements: longer class blocks for deeper learning, a move away from advanced placement classes, cornerstone initiatives like experiential travel and competency-based learning, the freshman and sophomore humanities programs, and limits on cell phone and social media use. 

When asked to share some other accomplishments, Tim mentions Cosmic Bandana Days right away. These “free days” are chosen by the head of school and announced when the fabled cosmic bandana appears somewhere on campus. Over the years, the bandana has shown up in all kinds of places, from the top of the flagpole in the front circle to the neck of Tim’s dog, Baloo. Today, the School has one Cosmic Bandana Day per term, which gives students and faculty the opportunity to slow down, unwind, and decompress. “To me, Cosmic Bandana Days are akin to group mental health days,” he says. “I try to announce them when I feel like the community needs a break.” 

The School’s rivalry with Millbrook is another highlight. The Battle for Route 44 — so named because both schools are located on the same road, 150 miles apart — is one of the biggest days on the school calendar. The daylong competition includes field hockey, volleyball, soccer, cross country, and football, culminating in the raising of the William Peck- Edward Pulling Trophy, named after the founders of the two schools. Since formally establishing the rivalry in 2021, Pomfret has won all four times. 

“The choices we’ve made are not whimsical or fad-based,” Tim says. “There’s good science behind each of them. Change is difficult for any organization, but at the same time, we must continue to put student well-being and student outcomes at the forefront of our decision-making process.” 

WHILE TIM WAS DEVELOPING The Pomfret Purpose and launching The Grauer Institute, Anne was defining her own role within the School’s future. A longtime yoga practitioner, she began offering yoga classes to students and faculty not long after arriving on the Hilltop. “In the beginning, I think my role was just to be present,” she says. “To listen, to show up, and to help hold things together.” 

Around the same time, Anne also began volunteering at a nearby social service agency called TEEG. “I ended up working the front desk,” she says, “answering the phone, helping out in the food pantry, just kind of getting involved.” 

Slowly but surely, Anne began bringing some of what she was experiencing at TEEG back to Pomfret. “I’ve always believed you should do service close to home. So that was a huge piece for me, wanting to teach kids the value of looking around the neighborhood and realizing that there are people in need right here.” 

During Project: Pomfret, Anne started a group called The Cinderella Project, inspired by the national nonprofit initiative which provides prom dresses to local high school students in need. A few years later, Anne established an on-campus pantry that provides weekend food bags called Pomfret Power Packs to nearby school children experiencing food insecurity. 

Anne was also instrumental in launching Pomfret’s newest academic department, the Wellbeing Department. Today, the department offers a long list of popular courses, including Bigger Than Ourselves, Becoming Kinder, Mindfulness, the Happiness Project, and Y Yoga?. 

“Well-being is about so much more than health,” Anne says. “It’s about learning how to take care of yourself so that you can take care of the people around you.” 

The physical embodiment of Pomfret’s commitment to well-being is the Tim & Anne Richards Health and Wellness Center, which opened its doors in the fall of 2018. This state-licensed facility features four single bedrooms with private baths, a multi-bed observation room, intake and consultation rooms, and three counseling rooms. Across campus, Strong Field House is home to a multi-use wellness studio, named the Anne Richards Yoga Studio, where students can take yoga and meditation classes. 

The project was made possible thanks to the generosity of Greg Melville ’68 and his wife, Susan Fox. Together, they contributed $2.975 million to make these spaces a reality. To date, Greg and Susan have donated more than $10 million to Pomfret, making them the most generous donors in the School’s history. 

“I am so grateful to Greg and Susan,” says Tim. “We now have three full-time licensed counselors, a full-time APRN who serves as our clinician, and a whole team of RNs. Our ability to better address student mental and physical needs is light years ahead of where we were just fifteen years ago.” 

ROOTED IN THE TIMELESS, HARD-WON TRUTHS of an institution more than a century in the making, Pomfret recently completed Amplify: The Campaign for Pomfret School, the most ambitious fundraising campaign in school history. The campaign, which was chaired by Melville, took shape following the release of Pomfret’s newest strategic plan, Change Makers and Problem Solvers, which sought to reimagine what a boarding school can and should be. 

“Too often, the problems we face can feel intractable, the magnitude of the change overwhelming,” Tim says. “But I have always been, and always will be, an optimist. I take it as an article of faith that one small school really can make a difference.” 

Amplify generated more than $82.5 million in capital, endowment, and operating support. “An $80 million campaign is huge for us,” Tim says. “It means our endowment has almost twice as much power as it did when we arrived fourteen years ago. It means we have more available financial aid to support students in need. It means we have more resources to support our faculty in their professional growth. And it means, after decades of conversation, we finally have a new science center.” 

The science center, VISTA, is the newest addition to a large list of capital improvements made to campus under Tim and Anne’s leadership. Opening in the fall of 2024, the three-story, 22,000-square-foot facility is double the size of the science building it replaced. The centerpiece is an airy space called the Hamilton Hub, with expansive windows stretching two stories, bathing the space with natural light. Beyond the Hub, the building branches into a labyrinth of classrooms, labs, and community gathering spaces. 

“VISTA has exceeded our hopes and expectations,” says Anne. “It has been enormously gratifying to see so many people rally around this missing piece of the puzzle. The opening of VISTA really has been a high watermark for us.” 

BACK IN JULY 2023, Tim and Anne took a trip to South Africa with some of their oldest, closest friends. “We were away from school, away from technology, in a place and time that allowed for deep reflection,” he recounts. That was when Anne suggested, for a whole host of reasons, that it was time to start thinking about life after Pomfret. 

Six months later, Tim officially announced to the Pomfret community: “Thirteen years ago, Anne and I arrived with our daughter Lucy to start a new chapter of our lives on the Pomfret Hilltop. As I reflect on the time that Anne and I have spent here, I am beyond grateful for the incomparably wonderful experience we have had at this special school. 

“Serving as Pomfret’s twelfth head of school has been the single greatest professional honor and privilege of my life. I consider myself incredibly lucky to have worked with as supportive a Board of Trustees as a head of school could ever hope for. Add to that the wisdom, compassion, and guidance I have received from my senior leadership team, and the fact is that I have been truly blessed.” 

In October 2024, after an extensive search, Heather Willis Daly was named Pomfret’s thirteenth head of school. Since then, Tim has been effusive in his praise of and support for the incoming head. “She brings energy. She brings charisma. She brings a deep love for working with teenagers. I’m really confident that she’s going to be that dynamic leader that Pomfret needs right now.” 

As retirement approaches, it’s clear that Tim and Anne’s impact will long outlast their tenure. “It’s not just about what we built,” Anne says. “It’s about who we built it with — and who we built it for.” 

In their final days on the Hilltop, Tim and Anne didn’t speak much about policies or programs. Instead, it’s the people they wanted to talk about — faculty who became more than colleagues, students who challenged them to become better teachers, trustees who offered wise counsel, friends and family who walked with them through joy and challenge. 

When asked what they will miss most, Tim pauses, and then smiles. “If you’re an educator and you’re leaving education, the thing you’re going to miss most is kids. I always wanted what was best for kids. If there’s a throughline to this story, that’s it. 

 

This story first appeared in the Summer 2025 issue of Pomfret Magazine.

 

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