Anna Dejdar ’04 Says Farewell to Shipley after 16 Years of Service

Anna Dejdar ’04 is set to embark on a new journey, leaving behind a legacy that spans over two decades. Having dedicated 16 years of her professional life and 7 of her student years at Shipley, Dejdar’s departure marks the end of an era. As she prepares to assume her new role as Head of Upper School at Stratford Academy in Macon, GA, the Shipley community reflects on her invaluable contributions and the indelible mark she has left on our School. “Among the many things that Anna has brought to Shipley and to me personally," says Head of School Michael Turner, "has been her love of the School and the way that love finds its way into our students and our program.”

The old adage, "If you want something done, ask a busy person to do it," encapsulates Dejdar’s role at Shipley. As the Associate Head of Upper School for Student Life and Dean of Students, she has been a cornerstone in Shipley’s Upper School, known for her relentless dedication, attention to detail, and versatility. Her tenure at Shipley saw her in myriad roles – from PAIS Self-Study Chair to JV tennis coach, and even creating the original interdisciplinary course, Psychology of Madness. Among these, her favorite is her current role, which allowed her to directly influence student growth and experience the dynamism of each day.

Dejdar’s commitment to Shipley and its community is deeply rooted in her love for her students and colleagues, coupled with the encouragement and freedom she received to grow professionally. "The students and colleagues are so special. I love working with them. I’m going to miss them terribly,” she remarks, highlighting the special bonds she formed at Shipley. This sentiment is echoed in her reflections on memorable moments – from her first faculty meeting and feeling like she was “crashing something” to the standing ovation she received for leading the PAIS accreditation process, and the mentorship she received from countless colleagues and mentors along the way.

Her impact on Shipley is multifaceted. Notably, Dejdar received the Margaret Bailey Speer Award for Teaching Excellence in 2016 and was honored by her students with a yearbook dedication in 2022. She played a pivotal role in reshaping student government, allowing students to have a significant voice in school events and traditions. Furthermore, her efforts in creating a consistent approach to handling academic integrity and behavioral cases have contributed to a more stable and transparent disciplinary process.

Despite her extensive involvement and achievements, Dejdar humbly attributes her success to the supportive and challenging environment at Shipley. “Every year I had a new challenge—a new class or a new position, which made my job so interesting. I had support, but at the same time, I had to figure a lot of it out on my own and that forced me to really learn about myself,” she states, underscoring her personal and professional growth during her time at Shipley.

As Dejdar looks forward to her new role at Stratford Academy, her departure is bittersweet. She leaves behind a legacy of leadership, innovation, and a deep connection to the Shipley community. In addition to her students and colleagues, “Knowing the history of the School, both preserving old traditions and helping to create new ones, having people stop by for candy or chocolate and just chat,” are among the things she’ll miss the most. Yet, the excitement for new challenges and opportunities in Macon, GA, awaits her, promising another chapter of growth and impact. As she steps into her future, her legacy at Shipley will undoubtedly continue to inspire and resonate within the community she has so profoundly touched.



Anna Dejdar ’04 Departure Notes
April 2024

Anna Dejdar ’04 has spent 23 years (more than half of her life) at Shipley—16 of them as a colleague and 7 as a student. At the end of this school year, she will say goodbye (for now) to become Head of Upper School at the Stratford School in Macon, GA.

Roles at Shipley: During her time as a Shipley colleague, Anna has served in a number of roles: Currently serving as Associate Head of Upper School for Student Life and Dean of Students. She was the PAIS Self-Study Chair, 11th & 12th Grade Dean, Director of Research, a JV tennis coach, and has taught a variety of classes including every level of Latin, along with Economics, 9th Grade World History, Modern European History, SEED, and French. She even created an original interdisciplinary course called Psychology of Madness.

Her favorite role over the years? Her current one, in which she has served for 7 years. She loves working with so many students, being involved in their growth, and that every day is different.

Awards & Honors: In 2016 she received the Margaret Bailey Speer Award for Teaching Excellence and in 2022 had the honor of receiving a yearbook dedication.

Why did she stay so long? “The students and colleagues are so special. I love working with them. I’m going to miss them terribly.” She also appreciates the encouragement she has received and the relative freedom she felt to grow professionally and to make meaningful changes to the office of the Dean of Students.

Favorite Memories: She can’t choose just one. She remembers fondly the students in her first Latin class, and how nervous she was to follow in the footsteps of Madeline (Emmy) Miller ’96, who the students had loved as their teacher the year before. She remembers planning her first homecoming dance, and getting a standing ovation from colleagues in recognition of her work to lead the PAIS accreditation (an arduous and important process for the School). Anna also remembers picking out furniture for the Gordon Center with students from her Action Research group, which had surveyed other students about what they were looking for in that space.

Her first memory as a colleague?
She clearly remembers attending her first faculty meeting. “I felt like I was crashing something,” she admits, attributing the feeling to many of her former teachers being in the room with her as colleagues.

Mentors: Char Weigel, who shared her classroom office with her. David Rich, who taught her Latin and then became her mentor. Emily Pickering, who taught her different ways to teach history. Former Head of School Steve Piltch was a mentor and pushed Anna to pursue advanced degrees, telling her, “You can’t teach the way you were taught.” She earned two master’s degrees while she worked at Shipley. Debbie Hoops was a mentor in French. Sunny Greenberg encouraged her to create the Psychology of Madness course. In her first year of teaching, Anna shared a classroom (and a room sign) with former French teacher and Director of Professional Development, Denis Asselin. “He wrote me a beautiful note talking about me as a teacher, everything I had learned and how I’d grown,” sharing it with a photo of the nameplate outside their shared classroom. Just one of the many special moments Anna has had at Shipley.

Gratitude for Shipley: “​​I'm so thankful for Shipley creating a nice safety net and comfortable professional environment, while at the same time pushing me. Every year I had a new challenge—a new class or a new position, which made my job so interesting. I had support, but at the same time, I had to figure a lot of it out on my own and that forced me to really learn about myself. Who I am now is so different than when I started. I don't know how many people go through that kind of transformation.” She adds, “I was involved in so many things because I wanted to be.”

#ShipleyProud: Anna is proud of her work in restructuring student government. When she first started advising the group, students didn’t feel like they had much agency or voice. Now, they are behind every major student event in the Upper School. Thanks to the efforts of student leaders under her guidance, spirit weeks are filled with fun events, t-shirt contests, and improving the Super Saturday experience for students to name just a few things she has accomplished. She was responsible for bringing back traditions like the junior-senior football game. Anna’s longevity in her role as Dean allowed her to establish processes and structures that have brought stability to the office. Though discipline isn’t fun, in partnership with Academic Dean Patti Lein, Anna contributed to the creation of a consistent and transparent process for academic integrity cases. She’s also really proud of her work in creating Psychology of Madness, an interdisciplinary course that students love.

Growing into leadership: As an introvert who has had to come out of her shell and step into her own leadership roles, Anna revels in helping students, especially the shy ones, find their voice. “Seeing those students come to life in a leadership position or different types of leadership positions has been really special.”

What she’ll miss: Traditions like Super Saturday, and all the rites of passage that come in spring. She’ll miss All-School Assemblies, especially the first and last ones of the year, where Oaks and Acorns make their special exchanges. What she’ll miss most: Being on Main Street, as she like to call the busy corridor where her office is located. “Knowing the history of the School, knowing the traditions, having people stop by for candy or chocolate and just chat.”

Anna’s next move? Head of Upper School at Stratford Academy in Macon, GA. “I’ll have a new position in a new school and new area—everything will be brand new for me, and I’m really excited about all of it.” Anna is looking forward to the new challenges and opportunities for growth.  


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.