There is a version of my life that never passed through Pomfret. That version looks very different from the one standing here tonight.

You are here to celebrate an institution that has spent over 130 years shaping teenagers into adults prepared to take responsibility for the world around them. I am one of those students, and now one of those adults.

I grew up in Brighton Beach, nicknamed Little Odessa for its resemblance to the Ukrainian port city my family once called home. My family came to this country because they were denied their livelihoods and their voices in the Soviet Union. It was a rare trade deal with Russia that allowed Soviet Jews like my family to escape.

As a high school sophomore, I spent a semester abroad in Israel. After a particularly moving day, I called my mom and declared that I would be joining the IDF as a lone soldier. There was a long pause. I thought I knew what she was thinking: I didn't fit my community's idea of a soldier. I was Jewish, from an immigrant family, a woman. Finally, she said: Olivia, America is the country that saved us. If you want to fight for the West, do it in the American military.

That conviction eventually led me toward West Point,  fulfilling my dream to defend the same freedoms my family had once only dreamed of. But it would not have led me there without Pomfret.

After returning from Israel, my previous boarding school abruptly closed. With weeks to spare before the start of my junior year, we toured schools in the Northeast, and my first visit to Pomfret ended up being our final stop.

My dorm parent showed me the ivy-coated Chapel and the window that would become mine. The first faculty member I met, an English teacher, spent time talking with me about books and poems and sent me home with a reading list that carried me through the rest of the summer. Pomfret took me in during a moment when my life felt unsettled, when the future was something I hoped for but could not yet rely on.

Junior year is pivotal for any student, and it is always a big risk to start that year at a new school. For me, it came with an added requirement: a physical fitness test for West Point. Pushups. Sit-ups. Pull-ups. A mile run. Fail any one, and you’re out.

I trained every day for months, and it went nowhere. Right as my frustration peaked, I had to choose a winter sport. I was assured by classmates that the girls JV hockey team was the most exciting, close-knit team to join, even though they rarely won games at that point. I have never been a good skater. I had never even played hockey. Cuts were announced, and I knew that I would be one of the players to leave the team. My last-ditch attempt: I volunteered to be the goalie.

Over the season that followed, I learned to trust my teammates, I learned how to make saves, and I learned to think twice before volunteering for a position that I was wildly unqualified for. One afternoon, our coach put a soccer ball at center ice and told us to forget our positions. Within minutes, we were laughing, slipping, and cheering for each other. The differences that had separated us — skill, speed, experience — fell away. For the first time, everyone belonged. One soccer ball deemed all of us beginner “soccer on ice” players, ready and willing to learn together, as a team. By the end of the season, the team had found its footing, and I was even named MVP.

A few weeks later, I went back to the gym. The pull-up bar hadn’t changed. The standards hadn’t changed. But I had. I approached the test the way I had approached that season — one rep at a time, willing to fail in front of others, unwilling to quit.

Pomfret taught me how to think, not what to think. It didn’t teach me how to avoid difficulty, but how to stay inside it long enough to grow.

That approach carried me through the rest of the West Point application process and into the next chapter of my life. Years later, I spent a summer working inside a federal agency responsible for protecting election infrastructure. The agency’s core mission mattered deeply, but the path forward was not necessarily obvious. No one had a ready answer for how to reach a divided public in a moment when trust was fragile. 

For me, this was another “soccer on ice” moment. I wasn’t the most senior person in the room. I wasn’t the subject-matter expert. But I listened, followed up with questions, and brought people from public affairs, cybersecurity, and policy into the conversation. And when there was no clear answer on how to reach a divided public, I built one — using the data I had, the voices around me, and the belief that even the most junior person can drive a mission forward if they’re willing to do the work. After pitching the idea to my boss, I pivoted from doing data analysis to leading the design of the organization’s first documented social media strategy.

I often think about my high school self, and the woman I am now: a West Point graduate, a Stanford journalist, an Air Force officer. Pomfret gave me room to arrive uncertain and still be taken seriously.

That kind of education does not happen by accident. It happens because of educators and classmates who are dedicated to building and maintaining a culture of inclusivity, creativity, and hard work. I would be remiss if I did not mention that Pomfret gave me two of my closest friendships to this day, Kayla Shah ’21, my roommate, and Andrew Edwardson ’21, both of whom transferred to Pomfret School as juniors that same year.

It also happens because of the people in this room. 

Pomfret is the kind of institution that takes students at uncertain moments — moments when their lives are still forming — and says, you belong here. That kind of education requires more than vision. It requires commitment. It requires investment. And it requires people who believe that giving young people time, attention, and trust will shape the adults they become.

The version of my life that never passed through Pomfret is not one I recognize. The one standing here tonight exists because this School chose to take me seriously before I fully knew how to take myself seriously.

Your support ensures that Pomfret can continue doing that — welcoming students who don’t quite fit a mold yet, challenging them to stay inside difficulty long enough to grow, and preparing them not just for college, but to become true leaders in their field of choice.

Thank you for believing in institutions that shape character, not just résumés.

Thank you for believing in Griffins before their futures are fully written.

And thank you for believing in Pomfret.

Olivia's remarks were made at Pomfret's Celebration of Philanthropy
event on Thursday, January 22, 2026 in New York City.

See More Stories