Diane Gandy: Riding the waves

By Jack Shea
Published: June 18, 2009

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Diane Gandy pays attention. In conversation, her eyes fix on the person talking, shifting only to identify sounds and movement around the lobby of the Chilmark schoolhouse where, until June 30, she is principal - head of school, in up-Island terms. Ms. Gandy will retire after four years of service to Chilmark's children.

Chilmark Community Center, Martha's Vineyard
This past Friday staff and children assembled in the Chilmark Community Center for Ms. Gandy's retirement party. Photos by Lynn Christoffers

After 34 years as an educator of small children, Ms. Gandy knows that children move fast and often in surprising ways. She has developed a second-nature ability to focus on the task at hand while monitoring her environment full of kindergartners through fifth-graders and a pre-school on premises.

But in its waggishly written annual report last year, the district also makes clear that administrating the shingled schoolhouse, home to 38 children, is a unique job: "Diane Gandy's multi-faceted role... includes even more than one might imagine is required of a leader of a small school housed in a building, the plumbing and heating systems of which are seemingly veiled in intrigue and mystery ... ."

Diane Gandy, Martha's Vineyard
A smiling Diane Gandy reflects on her four years as Chilmark's head of school. She will be retiring at the end of the month.

"No, it's not your typical job," Ms. Gandy says, smiling. "I get to fill in as a substitute teacher and custodian from time to time, and occasionally test the water - until Alan Wilder stepped up and volunteered to help." She points to a lanky, taciturn Islander working with vials and droppers at a table in the lobby. "It takes a village to raise a school," she adds, chuckling.

Clearly, this job has been a special experience for an educator used to the pace and challenges of big-city schools. Ms. Gandy spent more than 20 years of her professional life, teaching and administrating in Boston schools during the city's most turbulent educational period. Her career has included stops at The Blackstone School in the South End, The John D. Philbrick School in Roslindale, middle schools in Roxbury and South Boston and at the Clarence Edwards School in Charlestown.

In 2003, Ms. Gandy, who holds a master's degree in advanced education philosophy from Cambridge College, was faced with a life and career decision when she learned that Framingham was closing the Juniper Hill School where she had been principal for several years. "I always knew I would come here to live some day," the Roxbury native says. "I've been coming to the Island my entire life with my family. In 2002, my sister, Carol Sue Fuller, and I built a house in Oak Bluffs. Timing is everything. I had been a finalist for a principal's job here in 2004, so when the Chilmark job came open, I had some context with the district.

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