Reflecting on Thirty-Two Years of Teaching, Learning, and Adventure
by Matt Diller
In 1993, after three years of teaching in Japan and a youth spent wandering through Asia, Europe, Central America, and even up the road to Alaska with my thumb out, I returned home. I funded those adventures with odd jobs—cutting grass, substitute teaching, teaching English—and thought of myself as a citizen of the world.
Friends and family nudged me toward substituting at The College School. One step led to another: substitute, summer camp counselor, and then—quite unexpectedly—full-time teacher. My early collaboration with Sarah Hassing, Passport St. Louis, became the seed of the Third Grade neighborhood study, celebrating the rich diversity of our city. In Third Grade we traveled even farther, imagining First People 12,000 years ago; the Mississippians 1,000 years ago; and the Osage, French, and African American Creole communities who shaped St. Louis 250 years ago.
One of my favorite early memories is a small voice after a campout at Hawn State Park—“I discovered I was brave,” said Elise H. Another line that stayed with me: “Matt Diller has great ideas, and others like Mindy Bhuyan make them happen.” There’s some truth there.
I have been mentored, challenged, and inspired by master teachers: Margaret Rowe, Beth Connelly, Mary McGeathy, Mindy Bhuyan, Penny Allen, Nicole Post, and Will Langton. And I’ve been supported by steady leadership from Jan Phillips, Sheila Gurley, Ginny Altrogge, Ed Maggart, and Carl Pelofsky.
In my second year, I briefly considered returning to my life as a traveler. Jan Phillips encouraged me instead to keep teaching—but to keep wandering too. She sent me to Spain that summer, and I still draw on that experience (and my modest Spanish) to this day.
Since then, I’ve joined Field Ecology, Wilderness, Jefferson City, Chicago, Kindergarten Day in the Woods, Second Grade campouts, and Fourth Grade’s trip to Springfield and the Lincoln Library. I’ve traveled for professional development to Portland, Chicago, and across St. Louis. As a bus driver, I’ve supported bike trips, Middle School honeysuckle removal, and countless auction adventures to wineries, breweries, dinners, birthdays, and graduations. And of course, I’ve co-led roughly thirty field trips a year for thirty-two years of The Third Grade Experience.
I’ve loved the shared leadership of committees—diversity, building and grounds (for sixteen years), and the capital campaign. A visit with former art teacher MaryJo Wilmes in Austria sparked the idea for the water wall at the Jan Phillips Learning Center. TCS is a place where
inspiration becomes action, legacies take root, and new initiatives rise in capable hands. This gives me great confidence in its future.
Perhaps the greatest adventure has been helping shape the sustainable community in the woods at LaBarque Creek. Through Playful Learning, students have built hundreds of homes and businesses, enduring each season and reborn each year with fresh ideas. Their imagination has kept me young. They dream of inclusive societies, abundant economies, and healthy ecologies—and invite us to believe in them too.
At TCS we teach students to engage with their community and contribute to the world. I can think of no higher purpose. Whether through the Wagon Train of Food or the nearly $50,000 we’ve lent on Kiva.org through River City Market Days, our children learn that they can make a difference—and they do.
I turn sixty-four in March of 2026. After thirty-two years of the greatest honor of my life—teaching at The College School—I’m ready to return to the wider world, even if that sometimes means being a hermit on my five-acre homestead and letting the world come to me. I believe I’ve conjured a good life so far, and I intend to keep conjuring one. I wish the same for my colleagues: may you find as much meaning and magic here as I have. This is a place where dreams come to life.
Some of mine have included working with parents to bring us the drinking fountain, The River on Our Playground, solar panels, the wind turbine, our hallway displays, and—thanks to Sarah Hassing—Ember the Dragon, the tower, the rope ramp, and the saucer swing. If I’ve learned anything, it’s this: dreams come true when we share them. They become collective dreams, stronger than any one person’s vision.
At the close of this school year, I will retire. First, I hope simply to feel time and season more deeply, to contemplate the meaning of life, and to enjoy whatever adventures rise to meet me. I’ll still check in on Will and his new teaching partner, and I’ll happily lend a hand on a field trip, a lesson, an atlatl throw, or even a bus route—if needed.
Goodbyes are hard for me. I’m a practitioner of the Irish exit, prone to slipping quietly away from parties, weddings, even funerals rather than reveal too much emotion. This is an area of growth. I’ve contemplated this goodbye for years and have finally found the courage to say it.
Just don’t ask me to say it out loud—
or I’ll fall apart.
It’s time. Will Langton has been my partner in adventure for eight years, and he’s ready. Whoever joins him next will step into a journey unlike any other—and will discover, as I have, that at The College School, dreams come true.
–Matt Diller