Finding the Right Fit: The Flannelly Family’s Shipley Story
When Jenn and Dennis Flannelly moved to the Philadelphia area in 2019, finding the right school for their four boys—Jack ’24, Will ’26, Christopher ’28, and Thomas ’31—was a top priority. Having experienced both public and independent schools across multiple states, they knew what they were looking for: a place where each of their children could thrive in their own way.
“We have the all-American kid who loves sports, the Renaissance man into the arts, a tech-savvy thinker who’s passionate about technology and music, and one who loves theater, music, and squash,” Dennis says. “Shipley met all of those angles.”
The Flannellys’ journey to Shipley was fast-paced. Within weeks of relocating from Massachusetts, they visited several schools, but Shipley stood out. “There was just a different feel,” Jenn recalls. “The access to the people who would be working with our kids made a huge impact.” That access has made all the difference.
When one son struggled with math, his teacher called from home to discuss ways to help him build confidence. “He told me, ‘The goal isn’t just for him to get through the class, it’s for him to feel capable,’” Jenn recalls. Similarly, when Jack was in his final semester of senior year, his English teacher took a personal interest in his growth as a writer, ensuring he wasn’t just meeting the requirements but truly mastering the material. “Jack was doing well, but his teacher told him, ‘I can’t let you go until I know you feel confident in this,’” Jenn says. “It wasn’t about the grade—it was about making sure he had the skills he needed for the future.”
Each of their boys has found a place to shine. Jack, once quiet and reserved, became Athletics Committee Co-President his senior year and led awards ceremonies. In Middle School, Will discovered his passion for theater, later assisting with Lower School musical choreography as an Upper Schooler. Thomas overcame a tough transition, going from shy and reluctant in first grade to confidently leading his fifth-grade graduation as an emcee. And when Christopher was struggling with the transition to a new school—compounded by the challenges of the pandemic—his teacher went above and beyond to support him. “He would FaceTime him or call Christopher just to talk about history and music, because he knew those were the things he loved,” Jenn recalls. “He wasn’t worried about academics at that moment—he was focused on making sure Christopher felt seen and supported.”
Reflecting on their experience, Dennis appreciates Shipley’s emphasis on character and personal growth. “I love Shipley’s motto—Courage for the Deed; Grace for the Doing,” he says. “It’s not just words here. It’s lived.”
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