Jan Morris, Conundrum (1974)
The classic trans memoir that has stayed in print for four decades, Conundrum is engrossing reading as much for Morris’s ebullient prose and florid style as it is for glimpses of how her reading public viewed transsexuality in her time. Morris keeps it positive as she portrays her journey from a sensitive and prized young boy who’s convinced that he should have been born a girl, to her seemingly breezy path to actually living this reality; she views gender discrimination as one of the necessary evils of being a woman. Whatever obstacles she experiences stay firmly on the sideline, as Morris is eager to tell her encouraging tale, which may, I suspect, mask her struggles at a time when there was much greater stigma against trans women. Perhaps Conundrum's tone reflects Morris’s attempt to encourage other transgender women who fear the repercussions of transition.
Deirdre McCloskey, Crossing (1999)
McCloskey brings both her robust analytical skills as an economic historian and the unique perspective of someone who struggles to pass as cisgender to Crossing. In a clear-eyed dissection of gender transition through the metaphor of migration, McCloskey describes the harrowing experiences of trying to be perceived as a woman, including extensive surgeries, forced commitment to a mental institution, and the loss of her immediate family. McCloskey’s reductive view of the genders can at times feel unfeminist, as she tends to create sharp divisions between things that men and women do and the way each gender thinks. Despite this drawback, Crossing is an astute work that brings a great deal of lively insight into what it means to migrate to a new gender.
Jennifer Finney Boylan, She's Not There (2003)
In contrast to McCloskey’s analytical tone, Boylan’s approach is decidedly poetic. In She’s Not There , Boylan brings the reader close to her experience through a combination of humor and sincerity. The early parts of the book are particularly strong, especially when she describes her experience playing a game called “girl planet,” where she gets her wish and lands on a new planet that turns everyone female. Her struggle to maintain her family and adjust to her new relationship with her close friend, acclaimed novelist Richard Russo, are also key highlights. If Boylan’s humor can sometimes feel like it masks deeper feelings, it’s certainly a method that consistently wins the reader’s sympathy.
Janet Mock, Redefining Realness (2014)
The only book-length trans memoir written by a woman of color, Mock also distinguishes herself through her ability to be fully vulnerable without losing her focus. Framed as a confession to her future fiancé Aaron, Redefining Realness takes its reader through Mock’s difficult life – from childhood abandonment and abuse to her experience as a sex worker – while remaining grounded in deep personal insight. Parts of Redefining Realness do prioritize politics over subtlety, but it's the moments when it feels as though Mock is discovering herself through the process of telling her story that give readers the most impactful, searing portrait of self-determination.
Zoe Dolan, There Is Room for You (2015)
After gaining public recognition as the transgender lawyer who defended Osama Bin Laden’s son-in-law, There Is Room for You shows how this is only one of many episodes in Dolan’s storied life. Whether it’s in recounting her travails with men while struggling with sex addiction, or witnessing a close friend and dozens of other men in Egypt get arrested at a gay nightclub, Dolan’s prose is as lively as the stories she tells. But because the book jumps around so much as she describes her travels, it’s confounding when she slows down and settles on the factual world of describing criminal law, rather than the emotional one where she has battled many demons to get to a place of comfort with her gender and the rest of her life. But this doesn’t detract from the excitement of Dolan’s adventures, and her story of success despite the difficulties of her past.
Juliet Jacques, Trans (2015)
With a story as direct as its title, Jacques's Trans gives us a straightforward glimpse into what it’s like to medically transition through the British healthcare system now, while dealing with the struggles of a freelance journalist and student. Along the way, we also get to learn about previous transgender narratives in various media, as the book shifts back and forth between Jacques’ personal story and her analysis of the ways that other trans stories have been written. There are times when Jacques’ writing lacks energy in her effort not to present the trans women’s journeys as heroic. Nevertheless, Jacques come closest to conveying that as much attention as transgender women are getting today, many of us wish to be seen beyond our trans status, and that our existence has significance beyond this one aspect of our lives.