There are lives that feel like two novels stitched together. Deirdre Nansen McCloskey’s is one of them. The first book tells the story of Donald, a gifted Harvard graduate, economist at the University of Chicago, husband, father, a man admired for his intellect. The second book begins in 1995, when Donald steps aside and Deirdre takes her place. Crossing: A Memoir is where those two lives meet, and where the seam between them is laid bare for the world to see.
Her writing is unflinching. She does not shy away from describing the surgeries, the painstaking voice lessons, the awkward joy of shopping for clothes with the self-consciousness of a teenager. But beneath the details lies something deeper: a woman building herself in plain sight, learning how to be, not just look, female. It is a story of apprenticeship, not spectacle.
When I spoke with her for The Heroines of My Life, she gave advice that felt both tender and bracing: “Live your life as a woman. Don’t let being trans be your only identity. Make friends, go to church, join clubs, work with others. That’s how you truly become yourself.”
The costs of her truth, however, were devastating. Her wife of three decades, and the children they raised together, turned away. Her sister fought to have her institutionalized, and succeeded twice. These betrayals left scars that never fully faded. Yet McCloskey insists she would do it all again: “Even if I had known they would reject me, I would have gone ahead, sad, but determined.”
What saves her story from despair is her humor. On the cover of Crossing, she is captured in laughter, a moment of pure light. She remembers it vividly, the Economic History Association, 1999, her presidential address. A playful comment from the audience broke the solemnity, and she laughed, radiantly, as if to prove that joy could survive loss. Later she would say, “If you don’t have a pretty good sense of humor, I advise against crossing gender.” It is perhaps the truest sentence in her book.
McCloskey does not see herself as an isolated pioneer. She writes with gratitude about other women who crossed before her, Katherine Cummings in Australia, Susan Marshall of the Royal Navy, Jan Morris whose Conundrum startled the world in the 1970s. They mattered not just for their courage, but because they continued to live serious, respected lives. That is what McCloskey wanted for herself too: to be remembered not only as a trans woman, but as an economist, an intellectual, a teacher.
Yet Crossing is not only a personal memoir. It is also a document of its time. In the late 20th century, trans women were still framed in tabloids as curiosities, frauds, or threats. McCloskey’s choice to publish a serious, reflective account was itself an act of defiance. She knew that cultural imagination shifts slowly, often through art, film, or the pages of books. “Pop culture,” she once told me, “is where we do our thinking as a society.”By writing Crossing, she gave readers a way to think differently.
Looking back, she sometimes regrets the decades lost. At eleven, she already knew, but in the America of the 1950s, there was no path. So she built one life as a man, only to rebuild another as a woman. That double vision, seeing the world from both sides of gender, infuses her reflections with unusual clarity. She understands how fragile progress is, how easily respect can be withdrawn, and yet how essential it is to keep laughing, to keep going.
Today, she remains prolific, the author of more than two dozen books and hundreds of essays, holding a chair at the Cato Institute. Her scholarship stretches from economic history to political thought, but for many readers, it is Crossing that endures as her most intimate gift.
Because in its pages is not just the record of one person’s transition, but the universal question hidden inside it: What does it cost to be true to yourself? McCloskey’s answer is clear, if not simple. It costs everything, but it is worth more than anything.
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