How One Trans Activist Author Found Truth and Acceptance in Maine

Jennifer Finney Boylan on moving to the Pine Tree State, publicly transitioning, and the radical act of storytelling.

To get to the Boylans’ home in the Belgrade Lakes region, I drive across a narrow causeway that crosses Long Pond. On this early fall day, the car is surrounded for a moment by glinting sun and sparkling waves before the trees close in again around the quiet road. A few minutes later, I’m sitting with Jennifer Finney Boylan on her lakeside deck, looking at the pond through the trees. These are, she tells me, storied waters. “You know ‘Once More to the Lake’?” she asks, referring to E.B. White’s timeless 1941 essay about memory, fatherhood, and mortality. “It’s that lake. Well, actually the next lake over.” The rustic, peaceful place seems at first an incongruous home for Boylan—a woman known across the country as a transgender activist who’s appeared not only on Oprah but also on the reality show I Am Cait. She has just returned from a celebrity-studded New York City gala. But, like White before her, Boylan has found in Maine a special place for writers—and for people looking to become who they truly are.

Boylan and her wife, Dierdre, came to the region in 1988. Boylan, a promising young writer, had been offered a one-year teaching position at Colby College, and they expected to move on after that. “Deedie and I fell in love with where we were,” she says. At Colby and in the Waterville area, they discovered a community that suited them. “There’s a sense of connection, a sense of less bullshit here. It’s less about posing and more about a sense of truth.” It was a moment when the “struggle for truth” was very important to Boylan. “When I moved here, I was a closeted transgender person who wasn’t out, in some ways not living very honestly. One of the things I hoped to find in Maine was an ability to live a life that was a little truer to my own soul and the people around me.” For her first 12 years in Maine, Boylan was living as a man, the gender she had been assigned at birth. She had two children, became a beloved professor at Colby, published some successful fiction, and developed friendships with other Maine writers, especially the novelist Richard Russo. Her happiness was double-edged: she had known since childhood that she was meant to be female, but worried that coming out as a woman would mean losing much that she loved. In 2000 she began to publicly and physically transition from male to female. “When I came out, a lot of people didn’t know what transgender was. They thought I made it up myself,” she recalls. “But at Colby almost everyone was supportive. The people who weren’t supportive didn’t say it to my face, which is almost as good.” Boylan found her identity accepted outside the college, too. “Politics aside, people respect your privacy here. I can’t say that the last half-dozen years haven’t made me feel more afraid. It’s not all sweetness and light. But there is something about New England in which people generally leave each other alone. As weird as things have gotten, I hope that remains true.”

In 2003 Boylan published a memoir of her transition called She’s Not There: A Life in Two Genders. She describes its approach as “very human and relatable, instead of thinking of transgender people as rare creatures, like the duck-billed platypus.” The book tells the story of a boy carrying a soul-crushing secret through young adult-hood, marriage, and early career, then of a woman in rural Maine struggling through transition. It’s about the pain of living as some-one you’re not, and the costs—to self and others—of expressing one’s true being in a society that doesn’t allow it. When She’s Not There was published, “it took a lot of people by surprise, including its publisher,” Boylan says. The book was the first bestseller by an openly transgender American. Its success led to a two-day appearance on Oprah as well as a suddenly broader platform for Boylan’s work and words. Now, nearly 20 years after its publication, She’s Not There is a time capsule from a slightly different era, when people conducted relationships through long, searching email exchanges (some are reproduced in the book) and no singular “they ” or “them ” could pass an editor’s scrutiny. In some ways it shows what has changed in two decades. Yet, while the cultural presence and acceptance of transgender people has increased, a book that invites you into the life of a trans person remains a new experience for many readers. “I served as an object lesson that, yes, who I am and what I am is not so far from you,” Boylan says.

That message has remained central to Boylan’s work in the years since. She’s shared her story in three more memoirs—most recently Good Boy: A Life in Seven Dogs—that explore childhood, parenting, love, and other fundamentally human concerns. She’s published fiction for children and young adults and contributed to multiple anthologies on transgen-der issues as well as other topics. In 2014 she left Colby to become the Anna Quindlen Writer in Residence at Barnard College in New York City—a “dream job” that allows her to spend most of the year in Maine and to teach on campus in the spring. She also teaches at the Breadloaf Writers Conference in Vermont and the Sirenland Writers Conference in Positano, Italy. This fall, she’ll publish her first coauthored novel, Mad Honey, written with New Hampshire novelist Jodi Picoult. As a murder mystery, it might seem far removed from her usual concerns, but, told in alternating chapters by the murdered girl and the suspect’s mother, the book experiments with the idea of voice and explores, in the publisher’s words, “what we choose to keep from our past, and what we choose to leave behind.”

Boylan also devotes a good deal of time to nonprofit board work. She was on the board of GLAAD for seven years (and chaired it for four) advocating for the inclusion of LGBTQ+ people. After the end of her term at GLAAD, she joined the board of trustees at PEN America, an organization dedicated to the protection of free expression. She’s also just concluded a 15-year run of a monthly column for the New York Times, in which she linked her lived experience with pressing national issues, like abortion rights and presidential politics. She notes that she was the only trans voice regularly appearing on the opinion page, and expects to continue contributing “as my imagination, and/or the news cycle, demands.” Some of Boylan’s most popular pieces were about cocktails and dogs, but she tried to keep at least half of the content focused on LGBTQ+ issues. “It gets back to giving a voice to the normal, quotidian lives of LGBTQ+ people,” she says. “It’s showing that transgender people have children, have families, make bread, go to PTA meetings, vote, get their car washed. People think our lives are exotic. Just sharing all the joys of a quiet family life is a subversive act.”

So, the Boylans will continue to enjoy their Maine life, inviting friends over for patio cocktails and gourmet pizzas made in their outdoor oven, watching Long Pond sparkle through the trees. Boylan will continue to stretch her skills as an author: for the 2022–2023 academic year she’ll be a fellow at the Radcliffe Center for Advanced Study at Harvard University, doing research for a book about feminist pioneers. And she’ll be continuing her activism in her preferred form: writing. “To tell a story. It’s a radical act,” she says. “Tell me what’s more revolutionary than telling your story, telling it in a way that opens people’s hearts.”

A Jennifer Finney Boylan Reading List

She’s Not There (Crown, 2003; updated 2013). Boylan’s best-selling memoir is a seminal work of trans literature: a story of love, sex, selfhood, and understanding. The book is the story of “a life in two genders”—and the space between—but it’s also a love story: the tale of how James became Jenny and how her marriage survived, and thrived. The 2013 edition included a new updated chapter as well as a new epilogue by Deirdre “Grace” Boylan, Jenny’s wife. And it also includes an afterword by the Boylans’ beloved friend, Maine’s own Richard Russo.

If you prefer fiction to memoir, Boylan’s four novels provide mystery, humor, and wisdom. Long Black Veil (Crown, 2017) begins with seven college friends accidentally getting locked into the ruins of Philadelphia’s Eastern State Penitentiary one night, only to find that they are not alone. If you’re intrigued by Long Black Veil, you might also try Boylan’s first novel, The Planets (Poseidon Press, 1991). It’s the first book Boylan wrote after moving to the Pine Tree State, a story she wrote “during a time when I was newly wed, and new to Maine, and just in love with everything.”

The Falcon Quinn series (HarperCollins, 2010, 2011, 2016) is kind of the reverse of Harry Potter: young people turning into monsters are sent to a special school to teach them how to imitate human beings in order to survive in the world. It’s a not-particularly obscure metaphor for LGBTQ+ experience. Would you try to imitate someone you’re not, if it meant you could survive? Or would you embrace your true self, even if your true self were, say, a Sasquatch? Boylan wrote the three volumes with her then middle-school-aged children. “It was the most fun I ever had writing anything. Every day we’d come up with new monsters: A chupacabra? A were-chicken? I’m in.”

Boylan says her favorite one of her books is her memoir I’m Looking Through You (Crown, 2008) about growing up in an allegedly haunted house. It’s also an exploration of what it means to be “haunted,” and how we occupy our own bodies.

Don’t forget I’ll Give You Something to Cry About: A Novella, in which the Rileys of Bar Harbor drive to Ford’s Theatre in Washington, D.C., where their youngest, six-year-old Otis, is supposed to play “Flight of the Bumblebee” on violin for then-Vice President Joe Biden. Also in the car: recently transitioned trans teen Alex as well as the jubilant, impossible grandmother, “Gammie.” On page one, the Rileys pass by a group of chefs smoking cigarettes on the street. “What happened,” Gammie shouts out gleefully, “did somebody spoil the broth?”

“If I Had Loved Her Less: On a Queer Reading of Henry David Thoreau and the Daily Performance of Manhood,” LitHub, September 13, 2021

“Time Won’t Let Me Wait That Long,” The New York Times, December 9, 2020

“The Brilliant Uncertainty of the Grateful Dead’s ‘Dark Star,’” The New York Times, February 27, 2019

“What Peanuts Taught Me About Queer Identity,” The New Yorker, February 21, 2019

“How a Sliver of Glass Changed My Life,” The New York Times, September 4, 2018

“Inside of a Dog,” The New York Times, December 27, 2017

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