Driven by Curiosity: Getting to Know Our New Head of School Matt Glendinning

Incoming Hopkins Head of School Matt Glendinning has always been fascinated by what the past can teach us about the present. As far back as he can remember, exploring the treasures (both literally and figuratively) of the past has inspired him to tackle new challenges at every turn.

“What I’ve learned over time is that history is not some inherited set of facts,” said Glendinning. “You yourself are contributing to the writing of history.”

As Glendinning begins writing his new chapter at Hopkins following an enormously successful 13-year run as Head of Moses Brown, an N–12 Quaker school in Rhode Island, a look into his own history offers a glimpse into the person and leader the community will begin to get to know this fall.  

An Adventurous Learner

You can trace a lot of Glendinning’s decisions in his early years to what he refers to as having a “sense of adventure.” Beginning at age nine, for example, he left his home in Waterville, Maine, each summer to attend sleepaway camp on Lake Sebago, which took him away from home for several months each year.

“It wasn’t like going overseas, of course, but there was a lot of self-discovery and excitement as I made friends from many different parts of the country,” said Glendinning.

That same sense of adventure is what drove Glendinning to obtain a scuba license with his father after an interest in marine biology blossomed in high school. The idea of exploring the unknown depths thrilled him even if the local conditions were less than glamorous.

“Diving in the dark, frigid waters of Maine was not exactly what I had in mind, but I really enjoyed it,” laughed Glendinning.

Although he performed well academically in his elementary and middle school years, not everything was as smooth as his grades might suggest.

“I can assure all current Hopkins J School students that I was once a gangly awkward 13-year-old with acne and all the other social anxieties that go along with that age,” said Glendinning through a smile.

A voracious reader with a deep interest in environmental preservation as well as Roman history and the American Revolutionary War, Glendinning found comfort in the routine and structure of studying. He also felt a great deal of self-satisfaction from climbing each academic rung. His work paid off as he was accepted into Dartmouth College for his undergraduate studies.

Reflecting on his time as a young student, Glendinning is glad he had the autonomy to explore all of his interests as students are encouraged to do at Hopkins.

“I definitely credit my teachers and my parents who all gave me total freedom to pursue paths that I wanted to pursue,” said Glendinning.

A Literal Change of Course  

Unbeknownst to him as he entered higher education, Glendinning’s life path (or what he thought was the path) was about to change.

Glendinning began his freshman year at Dartmouth thinking marine biology or perhaps journalism would be his focus, but during his first week on campus, a conversation with a charismatic and captivating professor of Classical Archaeology sold him on the study-abroad element of the archaeology program. Despite never having been on a plane to that point, Glendinning was enticed by the thought of expanding his horizons. He was so enticed, in fact, that he didn’t realize that the first class he chose after deciding to pursue the new path—Greek Bronze Age Archaeology—was the hardest course of the entire major. He soon found himself overwhelmed by the sheer magnitude of it all; the seemingly endless number of artifacts to identify, important dates to remember, and ancient cultures to explore. That first semester, he struggled to keep up and wound up with a C on the midterm exam, the first of his career.

For someone who always expected the most from himself, surviving Greek Bronze Age Archaeology was a true test.

“It was ultimately a good thing because it provided a kick in the pants. It was a wake-up call that I needed to step up my game.”

Glendinning returned for the rest of the semester determined to do just that. He immersed himself in the subject matter, studied relentlessly, and walked out with a high grade and a newfound respect for the rigor of the field as well as self-confidence in what he could accomplish with his back against the wall. Glendinning still recalls the difficulty of those exams where students were presented with artifacts such as pieces of pottery and sculptures, and were asked to identify, date them, and describe their historical significance.

“To this day, I have a very strong visual memory that I trace directly back to that class,” said Glendinning.  

Worlds to Explore  

Following through on his wish to travel, Glendinning took advantage of his new major as he embarked on international studies. His first trip was to Greece in the spring of his sophomore year, where his passion for history and his penchant for exploring the unknown intertwined perfectly.

“I loved having to navigate unfamiliar circumstances as well as being able to apply language that I had been studying in the classroom to the actual real-world setting,” said Glendinning. He recalled how accomplishing something as small as successfully buying his own train ticket using modern Greek left him with a sense of empowerment.

“Traveling teaches adaptability and creativity, because no matter what you’re doing, you have to use problem-solving skills.”

In the years that followed, working on excavations in Greece, Spain, and Turkey, as well as helping to run a summer program at Cambridge University in the U.K., gave Glendinning a unique perspective on the magnitude of the world as well as its deep histories and mysteries. Although he no longer pursues archaeology in the intense way he did during and after school, since 2015 he has served as a Trustee of the American College of Greece, which takes him back there at least once a year to be among the people and places that inspired him years before. Glendinning also credits the process of research and the rigor of academic writing involved in archaeology with having influenced him greatly as an educator.

“In my writing and research today, I use my current environment as a laboratory to examine various issues in the field of education,” he said. “I ‘dig’ into whatever environment I find myself in as I identify learnings that others might find useful.”

Pursuing a Life in Education  

A surprising opportunity arose during Glendinning’s senior year of college that allowed him to teach a section of Latin to tenth graders. Although he had no formal training or experience in teaching, he dove in headfirst to see what the experience would be like. Once again, without knowing it, Glendinning was about to change 
the direction of his career.

“I loved teaching from the first moment. I was petrified of course, but by the end of the semester, I was all in.”  This experience led to Glendinning’s first job after college, teaching Latin at Andover, and to his pursuit of a Ph.D. in Classical Archaeology at the University of North Carolina, Chapel Hill.

After seven years of graduate studies, Glendinning’s former experience teaching at the secondary level lured him away from an anticipated career at the university level.  He taught Ancient and Medieval History, Latin, and Archaeology for eight years at Germantown Friends School in Philadelphia. In keeping with the old adage that you don’t really know a subject until you teach it, Glendinning remarked, “I learned more about ancient civilizations by teaching high school sophomores than I had in all of graduate school!”

Once again, it was the connection between the past and the present that most fascinated him. 

“I realized that, aside from electricity, many of the technologies we use today come directly from ancient and medieval times,” said Glendinning.

While focused on his classroom teaching—including a strong emphasis on experiential lessons such as creating a full-scale archaeological excavation for his students—Glendinning became fascinated by the systems and structures that support great teaching. This interest propelled him to complete a master’s degree in Educational Administration and to take on the principalship of the high school at Moorestown Friends School in New Jersey in 2004 and the headship at Moses Brown in 2009.

A lifelong learner, Glendinning made ongoing professional development and published writing cornerstones of his tenure at Moses Brown, elements he says he will carry forward at Hopkins. Much has been made of his viral snow day video that has amassed over four million views since hitting YouTube in 2015, but Glendinning is also 
a well-known voice in the independent school world and is widely viewed as a national thought leader in the sector.  

Excitement for Year One

As he prepares for his first school year at Hopkins, Glendinning says acclimating to the Hopkins community is priority number one. Adjusting to new environments in his summer camp days, his international adventures, and his journeys in the school setting have all prepared him well for this moment.

Glendinning is more than eager to get started.

“I want to be sure that my tenure at Hopkins is about people first and foremost. Not that programs, policies, and initiatives aren’t important, but I want to make sure that I know the Hopkins community very well and that I am engaging with students, parents, faculty, and staff in meaningful ways every day.”

Glendinning says he intends to spend a good deal of time in year one visiting classrooms to immerse himself in the Hopkins culture.

“To me, if I’m building on relationships first, everything else will come naturally. Devising and implementing new programs requires the input and partnership of faculty, and to that end, I want Hopkins’ teachers to feel known and know that I’m invested in their success.”

Outside of the classroom, Glendinning will also be a presence on the fields and courts across campus. Whether through soccer, skiing, tennis, swimming, or other sports he partakes in, Glendinning hopes to connect often with the Hopkins athletic community, “as long as I can stay injury free,” he joked.

Utilizing those memory skills he honed at Dartmouth, Glendinning says he has been studying the photos of all members of the Hopkins community so that he can walk onto the hill and match every face—faculty, staff, and students alike—with a name.

“While I’ll no doubt be surprised by the difference between real life and photos—students change quickly!—I am determined to know every student by name in my first year. If it takes hundreds of hours to do it, that’s what I’m going to do.”

We have Greek Bronze Age Archaeology to thank for that.  


This article was originally printed in the Summer 2022 edition of Views, the Hopkins School Magazine. 
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    • “In this photo, I'm probably around 8–10 years old. I’m holding a few gifts that my aunt had brought back from her several-year-stint in the Peace Corps in Botswana.”

    • “I might be 12 in this photo, circa 1976. I started playing soccer in 1970, and this photo is me in my club uniform (pretty sure the team was sponsored by Matthews Real Estate). It was taken in my front yard in Waterville, Maine.”

    • “My family skied at Saddleback Mountain in Maine for years, and this photo is probably from the early to mid-1970s (I look like I’m about 10 years old, which would make it 1974). Note the flashy warm-up pants . . . so ’70s!”

    • “Again, I seem to be around 10 or so in this photo, and I recall the exact moment. Christmas morning, and we were opening gifts. This particular gift was a very cool pair of ski pants (in my mind, an upgrade from the baggy striped ones from the previous photo!) and I am obviously excited!”

    • “I remember this exact moment . . . it was September, 1983, and I was in my driveway with a few of my best friends from high school, just moments before I drove off to college for the first time. If you look closely, I have tears in my eyes.”

    • “In 1989, I helped to lead a semester-long foreign study program in Greece for my alma mater, Dartmouth (a trip I had attended as a student in 1985 that launched my passion for Classical Archaeology). Here, exploring ruins in the Peloponnese.”

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Hopkins is a private middle school and high school for grades 7-12. Located on a campus overlooking New Haven, CT, the School takes pride in its intellectually curious students as well as its dedicated faculty and staff.