In the late 1990s, readers encountered something rare: a memoir about not just crossing boundaries of culture or class, but crossing the deepest divide of all, the line between male and female. Crossing: A Memoir, written by the distinguished economist Deirdre Nansen McCloskey, tells the story of a world-renowned scholar who chose authenticity over comfort, truth over convention, and laughter over despair.
Before becoming Deirdre, she was Donald: Harvard-trained, a rising star at the University of Chicago, an accomplished economist, husband, and father. His book The Applied Theory of Price shaped generations of students, and his work on cliometrics, applying quantitative methods to economic history, was at the center of an intellectual revolution. Outwardly, Donald had everything that a mid-20th-century academic life could promise. Inwardly, there was a secret so tightly held that even his loving, liberal parents never suspected.
The memoir begins with the rupture of that secret. In 1995, at the age of 53, Donald became Deirdre. She was among the very few academics of her stature to transition publicly in that era. Four years later, she published Crossing, which was named a New York Times Notable Book of the Year. Her prose, both sharp and self-mocking, details the steps of transition with candor: the facial surgeries, the voice training, the hours spent trying on clothes “like a teenager in front of a mirror.”
What makes the book remarkable is not just its honesty but its insistence on describing transition as a process of learning, a cultural apprenticeship.
In a conversation I had with her for The Heroines of My Life, she put it plainly: “Get on with your actual life as a woman. Don’t necessarily become a professional trans woman unless you have the political gifts of people like Andrea, Lynn, or Riki. Engage with cisgender women in church, clubs, or work.” Her words echo the practicality of her book: gender, she suggests, is not a performance for an audience but a daily practice woven into ordinary social life.
Yet the costs of becoming herself were steep. McCloskey’s wife of thirty years and their two children cut off contact, and her sister attempted multiple times to have her committed, succeeding twice. “Even if I had known that my wife and children would reject me, I would have gone ahead, sad but determined,” she told me. The memoir records this heartbreak without drowning in it, allowing readers to see both the pain and the resilience of someone who chose authenticity in the face of devastating personal loss.
What keeps Crossing buoyant is McCloskey’s humor. The book’s cover, showing her laughing in a moment of unguarded joy, is emblematic. She remembers that occasion fondly: her presidential address to the Economic History Association in 1999, where she laughed at a playful remark from the audience. “If you don’t have a pretty good sense of humor,” she later remarked, “I advise against crossing gender!” That humor threads through the memoir, balancing the sorrows with flashes of wit.
McCloskey also situates herself in a lineage of other trans women who inspired her. Katherine Cummings, the Australian librarian whose Katherine’s Diary touched her deeply; Susan Marshall, once a commander in the Royal Navy, later a university administrator at Oxford; and Jan Morris, whose Conundrum was one of the first transition memoirs to reach wide readership.What mattered most to McCloskey was not simply that these women transitioned, but that they lived serious, professional lives, respected for their contributions beyond gender. In her own way, she has become such a model, an economist with 25 books and nearly 500 articles, a public intellectual defending liberalism, and a mentor by example.
Her memoir is more than autobiography; it is also critique. She reflects on how psychiatrists, medical gatekeepers, and even family systems can become barriers to living truthfully. She explains why she chose to have surgery in Australia, far from the interventions of her sister and the obstacles of U.S. medical protocols. And she situates her transition within a broader cultural shift: in the 1980s, trans women in American media were depicted as freaks or predators; by the late 1990s, films like To Wong Foo, Thanks for Everything! Julie Newmar and Oprah’s television specials had begun to shift the conversation. “Pop culture,” she told me, “is where we do our thinking as a society.”
Looking back, she sometimes wishes she had crossed earlier. At age 11, she already knew, but in 1953, she explains, there was simply no possibility. Instead, she lived what she now calls “a full life as a man”, husband, father, tough-minded academic, before beginning another as a woman. That dual existence, painful as it was, gave her a unique vantage point. She knows, perhaps more intimately than most, the cultural architecture of gender from both sides.
Today, McCloskey continues her scholarly work, holding the Isaiah Berlin Chair in Liberal Thought at the Cato Institute. Her intellectual range remains extraordinary: economic history, rhetoric, methodology, liberal political theory. And yet, for many readers, Crossing is her most influential work, not because it explains the wealth of nations, but because it explains the cost of being true to oneself.
What lessons does she hope others might take? Some are practical, “avoid vocal surgery and do training instead”, others more philosophical: laugh often, live authentically, and do not underestimate the fragility of progress. As she warns, social acceptance can retreat as quickly as it advances. But her life itself, lived twice over, is proof that courage can carve out a space where there was none.
Crossing: A Memoir remains a landmark of transgender literature. More than two decades later, it continues to speak to readers who wonder what it means to cross boundaries that society declares uncrossable. For McCloskey, the answer was never simple, never painless, but it was worth everything.
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