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.”
When the Flannellys relocated to Philadelphia, they sought a school where all four of their sons could thrive. Shipley stood out—not just for academics and activities, but for the deep, personal support that would shape their confidence and growth.
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For over 20 years, Shipley’s partnership with alumna Paige West ’86 and the West Collection has brought world-class contemporary art to the Speer Gallery, inspiring students to think boldly and engage with real-world ideas.
Shipley’s Speer Gallery, led by art teacher Julia Staples, is a vibrant hub for learning and connection, showcasing thought-provoking exhibits that spark conversation and inspire collaboration across subjects like History, Science, and English.
Read about how Shipley changed life for Sissy ffolliott ’70 and why she supports the Centennial Society—ensuring future generations receive the same transformative education and encouragement she experienced over 55 years ago.
Middle School Science Teacher Ace Schwarz recently presented an education-focused project at the prestigious American Astronomical Society (AAS) Conference. Learn how Mx. Schwarz brings NASA research into Shipley’s classrooms, empowering students with authentic data projects and cutting-edge astronomy lessons.
To celebrate Black History Month, Shipley was proud to host Carlotta Walls LaNier, the youngest member of the Little Rock Nine, on Monday, February 3. Carlotta spoke to students and faculty about her story - for the right of every child to learn and grow without discrimination. She also spent time with the Black Student Union.
Congratulations to Aarik ’28 and Rohail ’26 for their creativity and award-winning excellence in the CMU CS Academy Fall 2024 Creative Task Competition, hosted by Carnegie Mellon University’s School of Computer Science.
Shipley’s Finance Club, hosted Tim Buckley, former CEO of Vanguard, for a discussion on career development, leadership, and the power of curiosity. Buckley shared practical advice on building a fulfilling career, the importance of asking thoughtful questions, and how purpose can drive lasting success.
Shipley’s dynamic history curriculum challenges students to think critically, engage deeply with diverse perspectives, and connect the past to today’s world. Explore how innovative electives and passionate educators bring history to life in 11th and 12th grade classrooms.
Shipley’s Middle School history classrooms are alive with creativity, immersive projects, and hands-on learning. From muckraking magazines to trench art, students don’t just study history—they experience it, making meaningful connections to the past and present.
The Shipley School Board of Trustees is pleased to announce the appointment of Ian L. Craig as the next Head of School, effective July 1, 2025. Mr. Craig brings more than 30 years of leadership experience in independent schools and a strong commitment to academic excellence, community engagement, and program innovation.
Over the past five years, Shipley’s Cross Country program has surged forward, blending competitive success with a vibrant culture of personal growth and team spirit. This rise has been powered by an engaged community of runners, dedicated coaches, and a program spanning Lower, Middle, and Upper School.
On display in Shipley's Speer Gallery from January 27 - April 4, 2025, an exhibition of paintings and sculptures addressing the urban landscape of Philadelphia.
Ranked #6 in the nation for U15 squash players, Kate reflects on her journey—from her first lesson with Coach Chris to joining Shipley's varsity squash team. Learn how the Shipley Squash Academy shaped her skills, mindset, and love for the game as she continues to tackle new challenges and reach for new heights.
It's easier than ever to stay connected and in the know about all things Shipley with our new mobile app. From calendars and lunch menus to photo galleries, directories, and ShipleyNet, the app keeps everything you need right at your fingertips. It also brings you content from Shipley’s main social media accounts.
Shipley’s annual Swamp Night is on January 24! Bring your family for food and fun with the entire Shipley community. Wear your favorite Shipley gear and join the Shipley Swamp to cheer on our basketball teams!
The Shipley School is a private, coeducational day school for pre-kindergarten through 12th grade students, located in Bryn Mawr, PA. Through our commitment to educational excellence, we develop within each student a love of learning and a desire for compassionate participation in the world.