37: Breaking Cultures of Silence, with Alex Myers
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The first openly transgender person Sara ever knew lived down the hall from her, during their first year at Harvard. This was 1996 - in other words, a time when being transgender wasn’t a common point of discussion, and most people likely weren’t aware if they’d met someone who was transgender.
But this classmate didn’t just talk about it in the walls of their first-year dorm, he talked about it on national television. And today, after thirty years, they’re crossing paths again to discuss his new novel and a question we can’t stop thinking about: what happens when we stay silent?
Author, educator and transgender rights advocate Alex Myers has spent about 25 years in prep schools, as a student, teacher, coach and now school director. His latest novel, While We Were Silent, imagines what real accountability could look like when the “boys will be boys” explanation no longer holds.
In this conversation, we explore why institutions protect their own, and what changes them:
Why “that’s just tradition” should be a red flag
Why who holds leadership, and whether they hold real power, matters more than the title
The glass cliff: when women and people of color are handed institutions already on the brink
How secrecy and “in-network” hiring let harm move from place to place
A hiring approach that draws on many perspectives, not just the future boss’s
Telling your story in a way that is authentic without being too close to the heart
Being an ally when no one from the affected community is in the room
When to engage with hateful questions, and when to walk away
A fiction-writing exercise for facing your fears
About Alex:
ALEX MYERS is an award‐winning author, educator, and speaker whose work sits at the intersection of gender, identity, and school culture. As the first openly transgender student at Phillips Exeter Academy and Harvard University, Alex has spent nearly three decades advocating for transgender inclusion while teaching in prep schools across the country. His long career in the classroom has given him a rare, firsthand view of how gender dynamics, power structures, and silence shape student life—insights that deeply inform both his fiction and nonfiction.
Alex is the author of several acclaimed novels, including Revolutionary, Continental Divide, and The Story of Silence. His newest novel, While We Were Silent, draws directly from his lived experience as a trans educator navigating the complexities of prep‐school environments—especially during periods of institutional reckoning around past and present misconduct.
Through gripping storytelling, Alex explores how communities confront harm, who gets believed, and what it takes to break long‐standing patterns of silence.
In addition to his fiction, Alex consults with schools worldwide on gender inclusion and is the author of Supporting Transgender Students, a practical guide for educators and parents. He lives in Vermont with his wife and two cats.
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