I grew up at Brimmer and May School (MA). For high school, however, my parents thought I should go somewhere bigger. I spent two years at a larger school nearby, but it never quite felt like home.
When I returned to Brimmer as a junior, Judith Guild, who was a teacher and the assistant head of school at that time, welcomed me with open arms and the quiet message that I belonged. I arrived as an anxious, uncertain teen who had not yet found his footing. I doubt I would have found it without her.
That was a long time ago. Now I teach at my alma mater, wrapping up my 12th year. As I watch Judy prepare to retire after 36 years at Brimmer, 14 of which as head of school, I keep coming back to the kid she let back in, thinking about the difference between who he was and who I am today.
I hope current heads of school take note, not just of what she has meant to me and my career, but of what she has meant to Brimmer as a whole. Because of her leadership, enrollment is up, and we have a new dining hall, expanded academic spaces, a state-of-the-art gymnasium, more classrooms on the way next fall, deeper curricular and athletic offerings, and stronger faculty benefits.
What’s more, Judy accomplished all of this while keeping the culture intact. Truly, she made our community better in every conceivable way without losing sight of what matters most: the people inside it.
Investing in Teachers
I first got to know Judy as a student in her AP English language and composition class. Her love of literature stuck out to me, but her enduring belief in my ability to grow intellectually was what, over time, truly transformed me for the better. Years later, after I returned to Boston following six years of teaching in Miami, she encouraged me to apply to Brimmer for an open history and journalism position.
Our long and close relationship means we can be honest with each other. We are often of like minds, but we speak directly when we disagree. This kind of openness is rare in relationships between teachers and a head of school, and I do not take it for granted. It has given me something most colleagues never get, which is a real look at how much Judy cares and her efforts to make Brimmer truly special.
Every time I asked her for funding to attend a professional development conference, she found a way. Every single time. I have traveled to conferences around the country, coming home with new ideas that I share with my students and colleagues. She also pushed me to share my knowledge. I have presented at national conferences on journalism and history education, built relationships with colleagues I never would have met otherwise, and come back a better teacher each time.
Here is what most teachers do not stop to appreciate about such experiences: Somebody has to decide they are a priority, fight for them in the budget, and protect them year after year. I believe Brimmer has the most talented faculty in New England, and part of why that is true is that Judy keeps investing in us—not just through salary or benefits—but by trusting us to go out into the world and grow.
I think about the kid I was—uncertain, a little lost—and the confidence it took for her to keep saying yes to him. She saw something I didn’t always see in myself. She’s still saying yes to me, and I hope she serves as a model for other heads in this regard.
Trusting Faculty
Judy wants her teachers to engage with the world: to write, speak, publish, and share what they know. She has always treated my writing as an asset rather than a liability, which I believe benefits both Brimmer and me. I’ve written for large platforms like Edutopia, The Atlantic, HuffPost, PBS NewsHour, and NAIS. I also maintain a personal site where I regularly share my thoughts on education.
Judy’s stance reflects a deeper kind of leadership, one that trusts in faculty judgment and has confidence that thoughtful commentary strengthens, rather than threatens, a school’s identity. I wish more heads led this way: trusting teachers and empowering them to act as ambassadors for the school.
Whatever profile I have managed to build, it exists because she created the conditions for it. She reads my work, tells me what she thinks, and has never once asked me to stop or pull something back. I have told her that I would stop writing publicly if she asked. She never has. She understands that shutting that down would cost me something real, and she wisely sees that a teacher who writes honestly about education reflects well on a school that takes education seriously.
Believing in Student Voice
Many heads say that they believe in student voice. Then you look at their student newspaper, and it is running puff pieces cleared by the administration. Judy is different, and The Gator is proof.
She backed both my students and me when we launched The Gator. That was 12 years ago. Today, it’s one of the most decorated student newsrooms in the country, at any school, of any size. This past year, I received a CSPA Gold Key and was named a Special Recognition Adviser.
These honors recognized The Gator’s status as a consistent Crown Finalist and my own contributions to the field, but none of it would have been possible without Judy. She provided the resources and, more importantly, the autonomy for us to succeed.
These awards have my name on them, but Judy’s fingerprints are all over them. Without her backing—the funding, the freedom, the institutional support—none of this would have been possible.
The Gator definitely gave her headaches over the years. That is what real student journalism does. But she never flinched. This spring, she signed onto the Private School Journalism Association’s Student Press Rights Model Affirmation Statement, giving Gator reporters protections equivalent to what New Voices laws provide public school students in Massachusetts: the right to publish, unless it would cause disruption or disorder at school.
I am the founding director of the Private School Journalism Association, a national organization that advocates for meaningful student press rights, and I have no doubt some of her fellow heads have raised an eyebrow at that. But she knows that The Gator stands for ethical journalism, and when we get something wrong, we say so and fix it. That kind of trust is rare.
Building a Legacy
The way Judy leads has created a culture of trust in our school community. I know more than most of my peers about how much she works—before anyone arrives, after everyone leaves, on weekends, over summers. Watching her lead that way raised my own bar.
I believe that once a school becomes more closely associated with its head than with the sum of its parts, something has begun to break. Over time, Judy has consistently pushed against that drift—not through statements, but through her actions. She has reinforced, again and again, that our school is larger than any one person, and that all of it deserves to be tended to and celebrated. That, to me, defines a great head of school. It also describes Judith Guild.
