You could have knocked Molly Haskell over with a feather. In October 2005, her younger brother, John “Chevey” Haskell, a 60-year-old self-employed financial advisor, husband and stepfather, announced his plan to undergo sexual reassignment surgery. Leaving marriage, business and Virginia behind, he will become she, Blue Ridge Mountains resident Ellen Hampton, with wardrobe, jewelry and makeup to match. She will undergo electrolysis, hormone therapy and multiple surgeries. “[A]ll of these will take place simultaneously and by stealth, so that Chevey will disappear and Ellen, like Athena emerging from the head of Zeus, will go forth fully armed as a woman,” Haskell writes in the memoir My Brother, My Sister: Story of a Transformation.

Haskell emphasizes that Ellen’s transformation is the greater labor, but she, too, is forced to evolve. “Where does it fit into the taxonomy of life crises when one person’s liberation is another’s loss?” she writes. Having relocated to New York City and established a career as a feminist movie critic and writer long ago, she surprised herself with some traditionalist fears. For example: Will Ellen still be able to offer tech support and do computational math like a man?

In the face of perceived crisis, Haskell employs culture in an effort to understand, i.e., devouring books, from first-person transitional accounts to medical treatises, Ovid to Orlando, and movies, Transamerica et al. Her other natural coping mechanism is off-limits: The day of the announcement, Ellen extracts a promise that Haskell will not write about her transsexualism. “I call it a compulsion, the need to write memoir, the need to understand, to make sense of something shocking,” says Haskell, who chronicled her late husband and noted film critic Andrew Sarris’ recovery from a mysterious illness in 1990’s Love and Other Infectious Diseases: A Memoir. “People are changed by something like [transsexualism]—not only the person who’s going through it, but those who love them.”

Regretting her promised silence (she had already selected the title for her new memoir), Haskell is delighted to hear, in 2009, that Ellen has changed her mind about allowing her sister to write about her. “She just felt that such a book might help others,” says Haskell. Ellen has second thoughts in 2010, frustrating her sister, who nevertheless shelves the book’s beginnings, before reissuing her blessing. My Brother, My Sister was mostly completed by the end of 2011, but the road to publication was bumpy. “Most publishers didn’t want to touch it, not just because it was a small minority market for a book, but just that it was a subject that made people uncomfortable, understandably. At first it is just baffling and mysterious and sort of disturbing,” says Haskell. “Who would choose to risk losing your family, losing your place in society, losing your friends, maybe losing your source of livelihood? .... If you’re not a convincing female you can be sort of ousted and threatened and murdered. It’s a huge risk on every level. You only do it if you just couldn’t do otherwise.”

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To people like Ellen, whose urges grew ever stronger as she aged, the need to transition can feel like a matter of life or death. With the bHaskell Coverulk of the process behind her, Ellen has never seemed happier, says Haskell—she is an outgoing, vivacious woman, well-loved in her community. What really stunned the neighbors? Her participation in the Tough Mudder obstacle course. “They just couldn’t believe she would endanger her hair,” says Haskell. The sisters recently promoted the book at two public events, in New York and Atlanta, and were met by supportive audiences.

Of course there have been other obstacles to overcome on their parallel paths to fulfillment and acceptance. “There is in this story of transformation no such thing as an unqualified triumph,” Haskell writes. Nevertheless, she advises those dealing with a loved one’s transsexualism to approach the situation with an open mind. “It is a bereavement. It is,” Haskell acknowledges. “You really are losing a brother or a sister, but not entirely, and you may be getting something very precious. Certainly you’ll be gaining the happiness of a sibling, and to me that makes its own argument.”

Megan Labrise is a freelance writer and columnist based in New York. Follow her on Twitter.