Woelper discusses his path to Cheshire Academy and what inspires him in the Fall 2026 issue of Independent School Magazine
Recently, Cheshire Academy Head of School Tom Woelper appeared on the National Association of Independent Schools (NAIS) podcast Member Voices to trace his career, how the school is addressing the widespread challenges of financial stability and AI in the space, and the enduring need for empathy and understanding.
The podcast performed so well that NAIS expanded it into a prominent feature in the Fall 2026 issue of Independent School Magazine, out now.
Asked what sets Cheshire Academy apart in the independent school landscape, Woelper pointed to the individualized nature of learning at Cheshire Academy. He explained the school’s International Baccalaureate® Diploma Programme, the Roxbury Center for Learning & Leadership, and the Global Citizenship Diploma Distinction are just some of the Academy’s signature programs.
“Many schools talk about meeting students where they are, and helping them go beyond what they thought was possible,” he said. “That’s something we do well at Cheshire Academy. There isn’t a single pathway here.”
Woelper also recalled his own time at Lawrenceville School, a teenager looking up to a history teacher who was also his dorm parent. The mentor taught his young student how to love and respect others, even when they made mistakes that needed correcting.
“Next to my parents and a few others, he’s probably the most influential person in my life,” he said. “That’s something that I’ve certainly taken throughout my work in schools and when I talk to kids or colleagues. Sometimes people might fall short, but I try to always come back to empathy and understanding.”
NAIS represents about 1,700 member schools and associations across the country, including 63,000 teachers and more than 738,000 students. You can learn more at nais.org.
Read the Article
Flip through the whole interview in the Fall 2026 issue of Independent School Magazine.
