Next year, Sylvan Oswald, assistant professor of playwriting in the UCLA School of Theater, Film and Television, will embark on a project that sheds new light on the events of Virginia Woolf’s popular 1928 novel, “Orlando: A Biography.” In “Orlando,” a young English nobleman mysteriously transforms into a woman and lives for more than 300 years, with the added benefit of not physically aging. It’s a narrative that is popular with scholars of gender and transgender studies. However, it doesn’t tackle transgender issues in an insightful or profound way. Oswald sees a benefit in using the story as a jumping off point to do just that.

His project, which may take the form of a series of texts, will be made possible by a prestigious Guggenheim Foundation Fellowship from the John Simon Guggenheim Memorial Foundation. In April, Oswald was one of four professors at UCLA to receive the honor, which is awarded to a broad range of scholars, writers and artists based on prior achievement and exceptional promise.

His interest in Woolf’s piece comes from his own relationship with the novel.

“When I first read ‘Orlando,’ I was looking for a trans hero,” Oswald, 40, says, “but because it was a ‘writer’s holiday,’ [what Woolf described as ‘a joke … and quick reading’] there was no struggle about the change of gender. Part of being drawn to ‘Orlando’ for my project was wanting to go back and unpack my initial reaction to the book. What would it look like if there was more awareness of thinking about a trans experience?”

Oswald’s work as an interdisciplinary artist revolves around plays, texts, publications and video that explore the ways identities are constructed. At the UCLA School of Theater, Film and Television, he has created two courses that have brought contemporary performance practice and theory to students. His work is borne not necessarily from plot but from imagery and language.

“Very often I’ll become interested in a drawing or a photograph or a piece of information that I hear, like a footnote,” he says. “It’s never a headline; it’s always some obscure, lost thing that I didn’t even know I had or some tidbit that has been forgotten; then I investigate it.

“My friend MJ Kaufman, who is also a playwright, talks about the materiality of language,” he adds, “which is thinking about language like clay instead of just information, to think about the sound of it or the shape of it or the speed of it; vowels and consonants and rhymes.”

Oswald’s latest book project, “High Winds,” created in collaboration with graphic designer Jessica Fleischmann, is an example of this idea. “High Winds” is one of the first two titles published by X Artists’ Books, an independent press that publishes the work of avant-garde and interdisciplinary artists. It’s an artist’s book, which, by definition, is an art piece that takes the form of a tome. Conveyed in an “associative, elliptical style,” “High Winds” follows the journey of the title character, a trans man dealing with insomnia, who takes a “hallucinatory road trip” to locate his estranged half-brother.

“Sylvan’s work is always compelling and forward thinking,” says Dominic Taylor, professor of theater. “‘High Winds’ is most telling as an object of performance itself, but he has taken it a step further, using it as a text for performance. It’s extraordinary to consider this complexity. Imagine a mobile by Alexander Calder, which is where I would pair the object of performance that is ‘High Winds,’ then consider that object recreated as a performance by a human being. It is profound and significant.”

Sometimes a title comes to Oswald quickly and then the writing process is an exploration of a “magical phrase.” “What is this? If it’s a character’s name, who is this? What are the elements of this person?” he says. “I spend a lot of time generating material in this way.”

Oswald often draws on personal experiences in his work. He enjoys letting an audience figure out what is drawn from real life and what is fiction. “I have often been a confessional writer,” he says. “As an artist, there’s a willing suspension of disbelief on my part that people may or may not see [a project] as true information about me. I’m actually quite interested in blurring that line … in a number of my projects, my web series ‘Outtakes,’ in particular, [audiences may say] ‘Is this happening? Is this not really happening?’”

The second season of ‘Outtakes,’ described as “a lo-fi mock-doc semi-improvised web series exploring transmasculine identity,” began Sunday, June 9, on the Open TV platform.

Oswald started writing plays at 13 and directing at 15. As an undergrad at Barnard College, Columbia University, he focused on both pursuits. Playwriting prevailed, however, and by the time he was getting his M.F.A. in playwriting at Brown University, he found that his knowledge of directing informed his writing.

“I’m really glad I learned how to direct,” he says. “That training helped me have a different perspective on playwriting. It really made me think about the entirety of the event of a show; to know about staging, to know about tech.”

Oswald says the Guggenheim is generally considered a mid-career award — and the idea that he’s at that stage in life takes some getting used to.

“It’s a kind of mental shift to think of yourself as moving from emerging to mid-career,” he says. “I’ve been precocious most of my life and I can’t be that anymore, which is weird.”

Even so, it’s a validation of his career.

“It’s a meaningful validation of the work that I have been doing up to now,” he says. “It’s as if members of the field are saying, ‘No, no, let’s take another look here. It’s not time for this person to go off into the sunset.’”