Sean Duncan

 

Mr. Duncan is thrilled to be back in Winchendon, Massachusetts serving as Head of School and Executive Director. Over the last 15 years, Mr. Duncan has engaged with and inspired countless students, young alumni, and colleagues as he has held various teaching and administrative positions on both Winchendon campuses.

Born in New Jersey but raised mostly in Northern California, Mr. Duncan eventually found his way to New England in 8th grade when his family moved to Barrington, Rhode Island. By his own admission, Mr. Duncan’s first few years in Barrington public high schools were rocky. In 10th grade, he transferred to Gould Academy in Bethel, Maine, and credits his boarding school experience at Gould with shaping his life’s work. Of boarding school, Mr. Duncan said, “That change was transformative. Through the care and support my teachers afforded me, I learned how to care for and support myself: academically, emotionally, socially. Then I learned how to care for others. I realized that I wanted to teach in schools dedicated to supporting good and bright kids who need something a little different.”

Sure enough, after sojourns back at Gould as a faculty member and in finance in Seattle, Mr. Duncan found his way to Winchendon in 2008 and was part of the original design team who pioneered Global Dynamics in 2009. After leaving briefly to teach at a charter school in NYC, he returned to Winchendon in 2014 to start the groundbreaking DoIT Academy. Many of the practice that are at the heart of a TWS education (ColLABs, self-reflective practices, immersive learning) all found their original roots in DoIT Academy, In 2017, Mr. Duncan was named Founding Head of The Winchendon School New York, where he oversaw the start-up and the growth of the School’s satellite campus first in Brooklyn, and then in Manhattan. Along the way, he has also earned master’s degrees from Middlebury’s Bread Loaf School of English and Columbia University’s Teacher’s College in addition to his BA from Whitman College in Walla Walla, Washington.

Blessed with an abundance of energy and ideas, Mr. Duncan has run several marathons, including the New York City marathon in 2019 and the Wachusett Mountain Race Marathon in 2017 (yes, running 26.2 miles up and down a mountain in Sean’s preferred mode of relaxation.) He enjoys playing golf, skiing, surfing, climbing, and anything else that involves endurance and a little bit of risk-taking. Right now, however, he gets most of his endorphins chasing his two young sons, Jack. (3) and Peter (2), around campus.

Mr. Duncan and his wife, Katherine, who was the Dean of Faculty and Staff and Director of Development at The East Harlem School in New York City for 14 years, live on campus in Homewood where they enjoy hosting the Winchendon community often, whether it’s a casual Sunday afternoon with football and homemade chili for faculty, cocktail parties with parents, or open study hall nights when students can come get their work done in the coziness and comfort of home.

• Go-to comfort food: I eat all the foods. All.
• On the bucket list: This will happen (maybe this year), but one day I will winter in Japan and slay the legendary JaPow (which means, I’d like to go skiing in Japan–always a place I’d wanted to visit for culture/food reasons, and Japan is also quietly known for having the most epic powder in the most epic of coastal mountain ranges).
• Which Winchendon class or ColLAB would you most like to take: I would love to take The Blues with James Harrington. First, James was a student of mine, so I think it would be pretty special to have him as a teacher. Second, I think the subject (and the chance to learn how to play the harmonica) is just so rich. It’s a wonderful opportunity to think critically about the history of America through a different lens than we traditionally get to explore it, and it would be a great chance to get out into the world, listen to some blues, and talk to some musicians.