Blog & Podcast Series 

Amy Thompson

with Amy Thompson, Dean of Enrollment

Amy's experience in admissions at independent schools and colleges as well as her years as a director of college guidance, give her a unique understanding of the admission process. Her goal with Genuine Admissions is "to provide some insight, guidance, and a healthy dose of perspective as families navigate the next step on their educational journey."


The Flight of the Hummingbird

In keeping with the school’s mission to foster one’s “best self,” the Board of Trustees supports a sabbatical program that allows faculty members, who have served the school for 10 years or more, an opportunity to apply for an extended period of time free from school responsibilities to pursue significant professional and personal development that will empower them to return to their work at Loomis Chaffee refreshed and with an enhanced ability to serve the school and our students. 

This past spring, I embarked upon my first extended time off in thirty years. (I’m not counting maternity leave as “time off,” as parental leave does not empower one to return refreshed.) Although I had professional development that I was able to pursue on my own time this spring, I was also free — and, thankfully, encouraged! — to rest and renew. As the vice chair of our Board of Trustees observed with a hand on my shoulder and twinkle in his eye when I informed him of my upcoming absence, “Amy, even hummingbirds have to land.” 

While formal sabbaticals have been offered by many educational and scientific institutions as far back as the early 1800’s, the concept of a sabbatical goes to the Biblical practice of shmita, where every seven years Jews working their lands would take a year-long break. Sabbaticals have become more popular across industries in the last decade; according to The Sabbatical Project, workplace sabbaticals have tripled in the past four years. Of course, COVID-19 has significantly impacted how many people regard their relationship to work; the value of taking time to reflect on the “why” behind what we do and how we do it has been brought into stark relief since 2020. Despite the media hype over the Great Resignation, some believe a more accurate representation would be to call the past two years a Great Sabbatical. 

That is, because for many, 2021 presented even more personal and professional challenges than 2020 when the world initially turned upside down. In admissions, the response across institutions to the immediate crisis was in lockstep: learn and implement a virtual enrollment process as quickly as possible. Colleges and independent schools battened down the hatches and worked hard to reassure prospective families that our institutions were providing the same trusted outstanding education and caring communities as we rode out the pandemic storm. A year later, admission offices were back to steering their own ships through rapidly changing and uncontrollable waters, trying to determine the right combination of both virtual and in-person processes that would serve a wide range of families. It was still very much a year at sea, and it took a full cycle for things to begin to settle down and feel a bit more like normal. In spring 2022 we were able to start to let out our collective breath. It felt like a good time to take a break and “land” for a bit. In addition, on top of the recent world events, I was ready to land for other reasons. It has been thirty years since I started my first admissions job in 1992, and I was excited for the time Loomis Chaffee provided me to rest, reflect, and renew.

Because I suffer from FOMO, I decided early on, like others before me, that the best way to rejuvenate would be to spend part of my time far from the Island. Because this was my youngest daughter’s last term at Loomis, I knew that I would be tempted to drive her to school so I could pop in and say hi to my admission colleagues or offer to pick her up so I could pepper her with questions about campus goings-on. I realized that if I was going to get the mental distance that the sabbatical afforded me, I needed to get some physical distance from campus. So, for six weeks I put thousands of miles between me and Windsor, spending most of my time traveling in Europe.   

Genuine Admission: I did not contemplate the tour guide training program or the value of a test optional admission policy while braving the rain and wind on a Yorkshire moor or while standing silently before St. Francis’s tomb. What I did do, as is typical when faced with the monuments of the past, is ponder the big questions. I found myself thinking more and more frequently about the “why.”  Not just the “why” behind plagues and pandemics, intolerance and violence, but the “why” behind what our schools, and more specifically, what I, do. What is it all for? I found myself wondering as I peered down into the arena of the Colosseum, pondering the fates of combatants centuries ago. What’s it all about, this quintessence of dust??!! 

Overdramatic? Absolutely. Cliche’? Without a doubt. Midlife crisis of an impending empty nester? I don’t think so. Because rather than leaving me despairing that working in boarding school admission isn’t along the lines of, say, painting the Sistine Chapel, I actually experienced the opposite. Standing in the nave of a ruined abbey on the edge of the North Sea, it was easy for me to be reminded that no matter how caught up one gets in the day-to-day, life marches on — and then to experience a wave of determination to make it a meaningful and impactful one, even if in a small way. I was more convinced than ever that schools like Loomis Chaffee and those who work to enroll it with curious, open-minded, and aspirational young people have a role to play in the betterment of this challenging, beautiful world. (Wow, this sabbatical thing works!!)

My sentiment was crystallized when my personal and professional lives collided again on the grounds of the Loomis family Homestead this spring when I watched my youngest daughter’s Commencement ceremony from the front row of the faculty section. Speaker Paul Mounds Jr., Class of ’03 and chief of staff to Connecticut Governor Ned Lamont, emphasized the importance of the friendships that he made at Loomis in developing his perspective at a formative age. In his address, he thanked former Loomis Chaffee Director of Admission Tom Southworth and my colleague, current Director of Admission and Financial Aid Nancy Cleary, for providing him the opportunity to learn about the world and his place in it from others who were from varying backgrounds but shared similar values. “We came to understand each other’s intent and purpose, but, more importantly, we learned to understand each other’s souls,” he eloquently observed. “Thanks to Loomis’ nurturing yet challenging environment, we each, individually and together, uncovered our best selves and learned to work for the common good.” He was speaking to the graduates, but he spoke to me as well.

Hummingbirds are the only vertebrae capable of hovering for a period during flight. I guess it’s not a huge surprise to those who know me that my mind was whirring away while resting. There’s nothing like being face-to-face with history, whether sitting in front of our Founders’ Homestead or gazing up at the oculus of the Pantheon, to make one contemplate the history we are currently living and one’s place in it. Yes, I was reminded frequently on my sabbatical that we humans are but grains in the sands of time. But as I reflected over the past three months on the past thirty years in my profession, the past two years of COVID’s impact on Loomis, and the ever-changing admission landscape still to come, I felt more strongly than ever that schools like Loomis and the admission offices that support them play an impactful role in developing the next generation of educated and active citizens like Paul Mounds. As he challenged the Class of 2022, “I didn’t realize that Loomis gave me the keys to help change the world. Now you have them too.” 



Previous Blog Posts

Recent Podcast Episodes

The Academic Program


In this podcast, Dean of Enrollment Amy Thompson speaks with Director of Studies Tim Lawrence and Dean of Faculty Andrew Matlack about the inspiring and exciting opportunities offered by Loomis Chaffee’s academic program.

A Conversation with Head of School Sheila Culbert


In this podcast, Dean of Enrollment Amy Thompson speaks with Head of School Sheila Culbert about Sheila’s hopes and dreams for the 2021–22 school year as well as our interdisciplinary programs; Center for Diversity, Equity, and Inclusion: new programming in digital and computational learning; and the soon-to-open Nichols Center for Theater and Dance.  

Senior Reflections


This past May, Amy Thompson sat down with seniors Kendall, Harry, Grace, and Max who took time to reflect on their four years at Loomis just days before they graduated. Their conversation provides wonderful insight into the student experience at Loomis.

Building Community Through Advising


Dean of Enrollment Amy Thompson sits down with Dean of Student Life Jessica Matzkin and Science Faculty member Ed Pond.

What Makes Loomis, Loomis?


Dean of Enrollment Amy Thompson answers one of the most popular questions we receive at Loomis.


Why Genuine Admissions?

An Introduction to Genuine Admissions, a blog and podcast series by Amy Thompson, dean of enrollment at The Loomis Chaffee School.

Genuine admission #1: My life goal was not to be a dean of enrollment at an independent boarding school.

Genuine admission #2: College admissions and boarding school admissions are not the same. But in some ways, they are.

Read More