Interview with Holly Cassaday
Date30 June 2025
Mediumborn digital audio file
DimensionsDuration: 27 Minutes, 29 Seconds
ClassificationsInformation Artifacts
Credit LineCommunity History Project Collection
Description(a) Audio file of interview with Holly Cassaday. She was interviewed by Samantha Hass on 30 June 2025 in Winsted, Connecticut (b) Photograph of Holly Cassaday provided by Holly Cassaday.
Holly Cassaday was interviewed as part of the Connecticut Museum of Culture and History's Community History Project discussing moments of change in her life.
Holly talks about her experiences being part of the board of the endowed academy, the Gilbert School, that she attended years ago. The high school, which her family has attended for generations, is important to her. Its significance in her life encouraged her to volunteer and become a trustee of the board.
As the chair of the board, Holly organizes meetings, works with the head of school, and signs off on certain financial documents. Her work here requires a great deal of scheduling and responsibility. She explains that her work for the school has been the result of climbing up the hierarchical volunteering ladder. She initially volunteered at her daughter’s elementary school for the PTO program, which mostly consisted of organizing fundraising events. Then, she volunteered for the town’s Laurel commission. Later, she found her work for the board to be the most satisfactory, as it directly impacts students.
Positively impacting students’ lives has always been a goal of Holly's. One thing that Holly describes fondly is the board’s role in increasing security and mental health resources for students at the Gilbert School. She explained in the interview that, post-Covid, the school had a need for increased mental health services, so counselors were hired to assist the students. An armed security officer was also hired for safety.
As a mother and someone with a full-time job, Holly explained that she uses calendars to track her responsibilities and has to plan her schedule with a great deal of intentionality in order to balance everything in her life. Fortunately, she has flexibility with her working hours, which allows her to dedicate time to volunteer services and board work. Overall, Holly spoke highly of her time on the board.
The biggest takeaway that she learned was to “keep an open mind and really think things through,” because working for a school board allows you to meet people of countless different needs and backgrounds.
Holly Cassaday was interviewed as part of the Connecticut Museum of Culture and History's Community History Project discussing moments of change in her life.
Holly talks about her experiences being part of the board of the endowed academy, the Gilbert School, that she attended years ago. The high school, which her family has attended for generations, is important to her. Its significance in her life encouraged her to volunteer and become a trustee of the board.
As the chair of the board, Holly organizes meetings, works with the head of school, and signs off on certain financial documents. Her work here requires a great deal of scheduling and responsibility. She explains that her work for the school has been the result of climbing up the hierarchical volunteering ladder. She initially volunteered at her daughter’s elementary school for the PTO program, which mostly consisted of organizing fundraising events. Then, she volunteered for the town’s Laurel commission. Later, she found her work for the board to be the most satisfactory, as it directly impacts students.
Positively impacting students’ lives has always been a goal of Holly's. One thing that Holly describes fondly is the board’s role in increasing security and mental health resources for students at the Gilbert School. She explained in the interview that, post-Covid, the school had a need for increased mental health services, so counselors were hired to assist the students. An armed security officer was also hired for safety.
As a mother and someone with a full-time job, Holly explained that she uses calendars to track her responsibilities and has to plan her schedule with a great deal of intentionality in order to balance everything in her life. Fortunately, she has flexibility with her working hours, which allows her to dedicate time to volunteer services and board work. Overall, Holly spoke highly of her time on the board.
The biggest takeaway that she learned was to “keep an open mind and really think things through,” because working for a school board allows you to meet people of countless different needs and backgrounds.
Object number2024.79.36a-b
NotesSubject Note: The Connecticut Museum of Culture and History’s Community History Project (CHP) is a public-facing initiative, focused on contemporary collecting, gathering items of the recent past as well as from events happening today. This program developed community historians to identify, document, and preserve their experiences as residents of Connecticut, and to share these experiences during a series of community presentations. The project focused on the theme "Redefining Moments of Change." Conneticans share stories of people or events who have changed their lives or how they have sparked change in the lives of others.Cataloging Note: Digitization and access to this collection is supported by a Congressionally Directed grant through the U.S. Department of Education.
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