New Charlotte Central School principal is all about making connections

It was at a summer camp after his first year of college that Tim O’Leary had a transformative experience. Working with kids who had individualized education plans changed his career trajectory and put him on a path to public education. This month, he started a new job as principal of Charlotte Central School.

Upon returning to the University of Vermont, O’Leary switched his major from biology to English with a self-designed minor in special education. He later obtained a Master of Arts in English from the Bread Loaf School of English at Middlebury College.

Photo by Tim O’Leary. Tim O’Leary on the first day of school this year.
Photo by Tim O’Leary
Tim O’Leary on the first day of school this year.

O’Leary’s initial goal was to teach humanities at the middle and high school level. His first job was at Middlebury High School where he spent half his time as a traditional English teacher and the other half as what was then called a reading teacher, working with the school’s biology teachers and their 10th grade classes.

Eventually, he began teaching at-risk students. He moved into a job helping teachers use digital structures in their classrooms at nine different schools in the Addison Central School District. O’Leary might get in his car after co-teaching kindergarten in Bridport and drive to Middlebury High School to work with honors juniors and seniors.

After two years, O’Leary decided to concentrate on one school at a time and was hired by Shelburne Community School. When the pandemic hit, he got a call from the director of curriculum at the Champlain Valley School District, asking him to build a virtual community. In the span of three weeks, O’Leary helped create and direct a virtual learning academy for 400 students, which wasn’t on his “career bingo card,” he said.

O’Leary’s next position was instructional coach and curriculum leader at Shelburne Community School. He received a Rowland Fellowship to create a more robust computer science curriculum across the district.

In June of 2024, O’Leary was hired by Charlotte Central School. He enjoys the fact that Charlotte doesn’t appear to have a parallel administrative structure with the district but rather works in tandem with the larger body. He likes the monthly assemblies which are attended by the entire student body and teaching staff. He believes those events help the older kids learn to interact with their younger colleagues.

O’Leary also appreciates the weekly staff meetings.

“Staff at Charlotte Central School are teachers, not middle school or elementary school teachers,” he said. “It’s lovely to see that unity and cohesion across the range of grades, functioning as a single community. That’s what drew me here and keeps me here and evolving.”

O’Leary’s work extends beyond Vermont. For the last 10 years he has been running What’s the Story?, a national program where middle and high school students consider a social issues that are important to them and put together a short documentary films.

A good deal of the program is virtual in places like South Carolina, Georgia, Maine, New Mexico, Kentucky and Sharon, Vermont. Evey month there is a three-hour Zoom meeting on a Saturday, and the entire group gets together over the summer, courtesy of grants O’Leary has obtained.

O’Leary describes the filmmaking program as a hobby. He also enjoys working with his hands and built his home in Ripton, despite not having a background in carpentry. He has two middle school daughters, and the family enjoys season passes at the Middlebury Snow Bowl.

O’Leary is entering his third year as Ripton’s town moderator. Last year, he brought that experience into the classroom to conduct a mock town meeting with his Shelburne students, a concept which he hopes to replicate at Charlotte Central School.

“There are a lot of great things that have happened and are happening at CCS,” O’Leary said. “My job is to figure out how to sustain those things and leverage meaningful change in ways that are exciting, authentic and connected to the community. What I’ve heard from Day 1 is people want to figure out ways to bridge connections between the school and the community.”

O’Leary is excited that one of those connections will be with The Charlotte News. The school has a journalism club, and he is hoping to hone their skills.

“Making connections brings me hope and joy,” O’Leary said. “There is a machinery of public education with budgets and schedules. We need to figure out how to do those things and still make space and design for joy.”