The following is a transcript of our 23-minute interview with Head of School Alixe Callen ’88, edited for brevity and clarity.
What are your favorite memories from the 2025-26 school year?
Dance Concert is always one of my favorites. That is such a community moment—you know that community is my favorite word. I thought that the football team winning the Macdonald Bowl last fall was another real hit. Brunswick, the school that they beat, is known for being this athletic powerhouse, so to beat them was a great achievement. I was really proud of those students. I loved that we moved our reunion weekend into the school year. The reunion gave our alumni the opportunity to interact with real-life students, which they really enjoyed. I think our students enjoyed it as well. I think it was nice for people to have a chance to meet the folks who came before the students.
The freshmen who entered Milton the same year you assumed the role of Head of School are becoming seniors. What advice do you have for them?
I think the dirty secret is that everybody thinks junior year is way harder than senior year when senior fall is actually much harder. The courses you’re taking tend to be harder, you are the leaders of your organizations, and you’re trying to make decisions about your future. Those decisions bring a whole emotional layer to the year. The good news is that senior spring is lovely. Also, remember that other students will be looking up to you. They will know who you are, so your actions have weight. You’re demonstrating to students what it means to be a Milton student. Finally, senior year is a time that a class comes together. I would encourage you all to lean into that, to really make an effort to get to know people who are outside your friend group and who have different interests than you do. That connection is really rewarding.
Don’t forget about Milton. We all go off and do our own thing, which is what we should do. But I hope that people will point back to their time at Milton as something that was really formative, will come back for reunions, will stay in touch with their friends, and will make Milton part of their lives going forward. One of my goals as Head of School is to create that kind of lasting community that people feel is always their home. I’m excited for this class to go forth—and to come back.
Do you have any particular memories of the graduating class?
I’ve really enjoyed watching them grow up and become leaders. Pati and Nemo, of course, excelled as Head Monitors. Their impact will be felt for a long time. I’ve been attending banquets celebrating various groups of students these past two weeks, and I’ve been struck by how many leaders there really are in this class. It warms my heart.
What parts of the Class of 2026’s leadership do you hope future classes emulate?
I love the way that they were so deliberate in terms of thinking about building community. Stables is a perfect example; seniors recognized that there are a lot of communities within the larger Milton community. Boarding and day. Athletes and non-athletes. Various ethnic and racial identities. They made the deliberate effort to ask: “what if we cross those groups?”
What are your goals for the summer and 2026-27 school year?
The most important thing that I’m responsible for is making sure that the students who are here now are having an incredible experience—that we are ensuring that the quality of teaching is amazing, the opportunities outside the classroom are compelling, and that the community here shares a common respect. Part of my job, though, is to be thinking about the Milton of the future. We have been working on a strategic plan, and the specifics will be ready to share out with the larger community in the fall. If we’ve laid out the direction, then we need to start doing, and that’s going to take everybody. It’s going to take students. It’s going to certainly take faculty and staff. And it’s going to take our larger community. So I’m excited to really lean into that and get going.