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.”
Shipley's new Head of Lower School, Tim Bickhart, is also the parent of Henry '28 and Jack '33. Learn more about what he loves most about elementary-aged children, what he considers to be great teaching, and what inspires him.
Join us on Saturday, September 27th at Super Saturday, a favorite Shipley tradition. The day-long excitement includes a kids' carnival, a free community barbecue, athletic events, and much more. Gather the family, wear your Shipley gear, and celebrate being a Gator!
With more than 75 clubs, ensembles, committees, and affinity groups, Shipley’s Upper School provides students with daily opportunities to explore their interests, develop leadership skills, and build community through a wide range of extracurricular activities.
Shipley’s Middle School Science Olympiad introduces students in grades six through eight to competitive science. Guided by teacher John Harris, the program blends hands-on problem solving with real-world application, inspiring curiosity in engineering, physics, biology, and more.
When Ian Craig stepped onto Shipley’s campus this summer as its 11th Head of School, he did so with a deeply rooted belief in the power of relationships and a steady commitment to what he calls “the work that matters.” With 20 years of experience as a head of school across a range of educational settings, Craig brings to Shipley not only expertise but also humility, humor, and heart. Learn more about Ian Craig.
Julia Fisher Farbman ’08 has built a career telling powerful stories. Her latest film, Audrey’s Children, honors pioneering oncologist Dr. Audrey Evans. Read this profile from the Summer/Fall 2025 issue of Shipley Magazine.
Marion Swett Robinson ’65 built a groundbreaking career in global finance, rising to senior leadership and helping shape modern markets through ISDA. Today, she extends her impact and support of others through wellness initiatives and nonprofit board service.
Shipley’s Middle School offers extracurricular opportunities that spark curiosity, build confidence, and foster connection. From Friday Clubs and gardening to creative writing and theater, students explore interests, develop new talents, and strengthen community beyond the classroom.
Lower School extracurriculars showcase how Shipley nurtures exploration at every age. This story is part of a broader look at how students develop confidence, creativity, and community beyond the classroom at Shipley. Learn more in this story from the Summer/Fall 2025 Shipley Magazine.
From mandolin and debate clubs to SWINE and Sprouts, Shipley’s extracurricular life has reflected student passions for more than a century. This archival look traces the evolution of activities that have shaped the experiences of generations of Shipley students.
Beginning January 5, 2026, Shipley’s Upper School will adopt a cellphone-free school day policy, building on a successful pilot and reflecting the School’s commitment to student well-being, engagement, and community connection.
In 2024–2025, 19 Shipley students earned the Global Seal of Biliteracy, a nationally recognized credential demonstrating proficiency in English and another language. Students achieved this distinction in Spanish, French, and Mandarin.
Learn about Shipley from members of the Class of 2025, who reflect on their journeys, celebrate meaningful relationships, and share the wide range of academic, artistic, and athletic experiences that shaped their time here.
Read about the life and legacy of Gary Gruber, Shipley’s Head of School from 1985 to 1992, a deeply compassionate and visionary educator who guided Shipley through a pivotal chapter of growth, change, and renewed purpose.
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.
Thirteen members of Shipley’s Class of 2025—including student-athletes in soccer, basketball, lacrosse, softball, squash, swimming, and track—will continue to compete at the collegiate level, carrying their talents and Gator pride to campuses nationwide.
Shipley’s Track program delivered a strong year, with athletes earning championship titles and multiple medals across winter and spring meets in running, throwing, and jumping events.
Richard Liu ’25 founded Shipley’s Mock Trial Club as a tenth grader. Now with more than 30 members, the club competes statewide while fostering skills in public speaking, analysis, and collaborative learning.
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.