Many first encountered Daniel Lavery on the Toast, a feminist website the now-33-year-old cofounded in 2013. The Toast was considered a rarity among media startups for its thoughtful, positive, and supportive online community. Lavery’s debut essay collection, Something That May Shock and Discredit You, bowing from Atria in February, addresses topics he explored with the Toast: literary dirtbags, puzzling Biblical parables, and historical jerks.

While the book picks up on familiar themes, it also explores a new one. Lavery came out publicly as transgender in 2018 and recently adopted his partner Grace’s last name, and, in the collection, he grapples with how to understand his transition by examining it through the lens of the Christian and pop culture narratives on which he was raised.

The collection also has echoes of Texts from Jane Eyre, Lavery’s 2014’s literary mash-up in which he reimagines classics as series of text messages. That debut was followed by the 2018 horror-tinged short story collection The Merry Spinster, which explored the fluidity of gender amid the strangeness of fairy tales.

Lavery, who spoke to PW by phone from his home in Oakland, self-deprecatingly describes Shock and Discredit, which is being published under the name Daniel Mallory Ortberg, as “a very shallow and disjointed memoir, or a series of loosely connected thoughts about the bits of pop culture and books that have shaped me into the person that I am—or something in between.”

Lavery’s prose is erudite, self-effacing, and welcoming—in other words, reminiscent of the style he displayed at the Toast and later honed at Slate, as the site’s “Dear Prudence” advice columnist. Reading his work feels like sitting down with a charming acquaintance, a favorite coworker, or your coolest neighbor.

The essays circle around a constellation of topics familiar to longtime fans of Lavery’s work—including subjects such as, in Lavery’s words, “Why have I historically felt compelled to call Captain Kirk a lesbian? What does it mean that I’m no longer able to look at myself in the mirror? How do I find myself experiencing time differently now that I’m transitioning?”

The collection occasionally feels recursive, which fits well with the book’s themes of coming out and transitioning—of trying to fit disparate parts of a life together into a single narrative. That repetition is something Lavery feels conflicted about. On the one hand, examining and reexamining familiar stories is important work. On the other, he confesses that it sometimes makes him feel trapped, like his life is a series of recurring phases: “What I thought was an attempt to dig myself out is instead taking the same left turn a hundred times, and I’m back where I started.”

This feels especially poignant when Lavery uses biblical parables to discuss transitioning. Shock and Discredit opens with a meditation on Lavery’s evangelical childhood and obsession with the rapture. He describes it in the book as both seductive and terrifying, “a day when time would burst and unspool itself in every possible direction, and all those willing to be perfected would be milled down by the grindstone of heaven in a lovely terrifying roar.”

That sublime terror now serves as a road map for Lavery in examining his own realization of being transgender and his subsequent transition—or, as he refers to it in the book, “a rootless homesickness that translated quite neatly, for a religious 11-year-old, into heaven-longing; later it would translate quite neatly, for a nervous 31-year-old, into transexuality.”

Lavery is sensitive to the pressures placed on trans people to form cohesive narratives, to prove that transitioning is not an impulse, that trans existence is not a passing phase or fad. His humor turns sharp when it’s aimed at how cisgender society forces its own narrative onto trans people.

The essay “Did You Know That Athena Used to Be a Tomboy?” side-eyes the transphobic rhetoric that trans men are somehow responsible for gender roles becoming more rigid. The essay “Pirates at the Funeral: 'It Feels Like Someone Died' but Someone Actually Didn’t” pokes fun at the overwrought grieving process that can greet newly outed trans people. It’s a process in which their closeted past selves are mourned, forcing trans people to comfort those who treat transition as a spiritual death instead of a new beginning.

Lavery calls on a multitude of religious and cultural figures to help him and his readers navigate the different turns of transitioning. He quotes both The NeverEnding Story and the gospel of Luke when writing about the dissociation and self-denial of his pretransition days. In Help Me, Brother, or I Sink, he reimagines himself (“simultaneously an embarrassment to feminism and transmasculinity”) and an unnamed yet perfect transmasculine You (“gendered correctly and casually by everyone but would react with disarming strength and grace if you ever happened to be misgendered”).

“I’ve felt such internal pressure at so many points to be accommodating, to have as few needs and boundaries as possible,” Lavery says of his transition. As for external pressures, he adds, “Sometimes someone will say something like, ‘I need time,’ or, ‘I don’t understand this.’ That makes sense as an initial response, but when someone says that over the course of years, I start to think, ‘Why are you in the exact same place of not understanding?’ ”

Lavery adds that it prompts a more general question: “What can we ask of people? What can’t we ask? What does it mean to accommodate versus enable?”