Alexus Sheppard - From Both Sides Now

2017, Alexus Sheppard, English, Interview,

Full title: "From Both Sides Now: One Woman's Journey to Love and Living Life to Its Fullest" by Alexus Sheppard.

When Alexus Sheppard speaks about her life, she does so with a disarming blend of candor and humor. Her memoir, From Both Sides Now: One Woman’s Journey to Love and Living Life to Its Fullest, is not just a chronicle of gender transition but an intimate story of courage, love, and self-discovery.

 

In my Heroines of My Life interview with her, she described herself as “an outsider since childhood,” never quite fitting into the mold that her conservative Christian upbringing in rural Kansas tried to impose. That sense of otherness became the seed of a journey that would eventually reshape her entire life. For years, Alexus lived under the name Allen. On paper, he had everything, a family, a comfortable home, financial security, but inside, he felt fractured. She told me that for a long time she tried to rationalize her feelings by labeling herself “just a crossdresser,” a compromise she hoped might preserve her marriage. But the truth was louder than the label.

 

In 1997, a makeover session at a Denver gender salon became a turning point. “It was the first time I looked in the mirror and saw myself,” she said. The experience cracked the wall of denial, though it would take a cancer diagnosis the following year to push her fully toward authenticity. Cancer, with its brutal mix of chemotherapy and radiation, clarified everything. As she put it, life was simply too short to waste on pretending. That insight became a guiding principle: when faced with fear or uncertainty, choose love and truth. “No matter the question,” she told me, “the answer is always love.” Alexus’s path to authorship began online. In the late 1990s, she created one of the earliest transgender blogs, a raw and honest space where she shared her evolving identity. Readers resonated so strongly with her words that they urged her to write a book. She hesitated until an unlikely encounter in a San Francisco oyster bar connected her with publishing professionals who helped shape years of blog entries into a cohesive memoir. 

 

What began as personal journaling grew into From Both Sides Now, a book praised for its warmth, wit, and grace. The memoir’s heart lies not only in Alexus’s transition but in her love story with Deborah, her wife and life partner. She recounted their wedding to me with a sparkle in her voice: beneath towering redwoods, wearing a custom-made gown, she felt like she had stepped into a fairy tale. Yet Alexus is quick to emphasize that such joy comes from an inner transformation first. Love of another, she believes, can only be sustained by first loving oneself. Her story also stretches beyond the personal. In our conversation, Alexus reflected on the changing landscape of transgender visibility, noting that acceptance often mirrors political winds. She is sharply critical of how transgender lives are portrayed in media, too often reduced to clichés or tragedies. What matters most to her is ordinariness, the chance for trans people to be seen as full, everyday human beings rather than spectacles.

 

Alexus draws inspiration from trailblazers like Christine Jorgensen and Lynn Conway, but she also insists that progress depends on quieter, everyday courage. “Sometimes it’s just one person living openly that changes a whole community,” she told me. That philosophy shapes her activism: not grandstanding, but presence. Reading From Both Sides Now feels less like flipping through a memoir than sitting across from a friend who has lived deeply and is willing to tell the truth about it. Alexus is unflinching in sharing her pain, struggles with dysphoria, fear of rejection from her children, the physical toll of cancer, but she is just as unflinching in celebrating joy: the pride she feels in her daughters, her partnership with Deborah, and the peace of living authentically.

 

Her journey, as shared in both her book and our interview, is a reminder that authenticity is rarely convenient, often frightening, but always worth it. For Alexus, stepping fully into herself was not only an act of survival but of love, for her family, for Deborah, and most importantly, for herself. More than a memoir, it is an invitation: to stop silencing the inner voice, to choose love over fear, and to discover, as Alexus did, that the most radical act of all is living as who you truly are.

Available via Amazon

and The Heroines of My Life

Photo via The Heroines of My Life

 

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