Every new school year at Milton Academy is filled with promise and opportunities for growth.
Speakers at this year’s Convocation—the Upper School’s official kick-off to the academic year—encouraged students to take chances, support one another, and explore the unknown. Co-head monitors JP Giglio ’25 and Ariam Gebresilassie ’25 talked about their journeys from their first days at Milton to the start of their senior year. Both said they grew in their confidence and sense of belonging because they felt embraced by the Milton community.
Ariam, a boarding student from Minnesota, recalled the “leap of faith” she took in choosing Milton, and shared that although she was nervous when she first arrived, her peers in her dorm and soccer team made her feel welcome and capable of finding new passions.
“If I hadn’t taken the time to introduce myself to new people, to really engage with those around me, I might not have found myself standing here today, speaking to all of you,” she said. “I invested in this community because I wanted to experience everything Milton had to offer. And that investment began with my simply showing up and being fully present, and grew into taking risks and putting my heart into every opportunity. That’s what I want to encourage each of you to do this year. Don’t just go through the motions. Dive in headfirst. Show up for your friends, try something new, and don’t be afraid to stand out… Milton is a place where, if you are so unequivocally yourself, you’ll be rewarded.”
Jumping into the Milton experience with enthusiasm and an open heart pays dividends, said JP, a day student from Massachusetts. He shared a funny story about an embarrassing moment early in his first year, remembering that a network of friends instantly gathered to support and laugh with him.
“I learned that if you don’t do something once, you will never know if you want to do it a second, third, fourth, or even fifth time,” he said. “I’ve also learned that some things just won’t go the way you expect, especially the first time around, but you can find a silver lining in every situation that does not go your way so long as you have an open mind. For me, after being comforted by my friends, I had all of the reassurance I needed to know that Milton was going to be my home.”
Convocation was an opportunity for the entire school to meet new Upper School Principal Rachel Stone, a lifelong boarding school educator who started at Milton July 1. Finding her passion for teaching and living in a school environment in her first-ever school job was a life-changing surprise, she explained, asking new and returning students to keep their minds open to new opportunities.
“You won’t believe how exciting your academic journey will be at Milton, and you may be surprised by a course you fall in love with or a passion sparked by a certain book, art project, lab design, or new language,” Mrs. Stone said. “When we keep our eyes and hearts open, the next steps can come into view in unexpected ways.”
Head of School Alixe Callen ’88 shared her joy about reaching another first day of school, describing the feeling as a combination of a birthday and every holiday at once. Milton is a community that celebrates and uplifts its members, especially rewarding those who support and engage with others. Every year brings countless examples of students selflessly showing up for one another, for the school, and for the world beyond.
“If we are truly preparing you to go out and be active and engaged citizens, you need to practice,” Dr. Callen said. “You need a place where you can try things out, where you can learn how to lead and how to follow. Where you learn to advocate. Where you learn to listen and to speak. Where you take responsibility for something larger than yourself. Where you learn to champion the people sitting next to you. I love witnessing these things happen on our campus.”
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