As a prose writer, Dearman has had both fiction and nonfiction published. Her book, Bang the Keys: Four Steps to a Lifelong Writing Practice, (Penguin/Alpha, Summer 2009), is based on her work as a writing coach. An eclectic writer, Dearman is also the author of the books, Queer Astrology for Men and Queer Astrology for Women (both from St. Martins Griffin, 1999). Her essays and short stories have been published in numerous literary magazines including North Atlantic Review, Lilith, The Portland Review, Griffin, New York Stories, Thereby Hangs A Tale, Mr. Beller's Neighborhood, Cantaravile and Harrington Lesbian Literary Quarterly. Her short fiction has been anthologized by Cleis Press, and she is the winner of The First Place Prize for Fiction from the Vera List Center for Art and Politics at The New School.

Frequent themes in her writing include bygone eras of New York City, as well as spirits, and the metaphysical world. The tone of her prose often blends humor and melancholy.

Dearman is a recipient of The Stephen Sondheim Young Playwright’s Award for her play Levitation; her plays have been performed at The Westbeth, Performance Space 122, The Perry Street Theater, Dixon Place and numerous other venues. Laurie Stone called her “a risk-surfing playwright” in The Village Voice. She developed one of her plays, The Great Bravura, into a short film which was presented at several East Coast festivals.

As a journalist, her features have been published in The New York Daily News, Time Out New York, Nextbook, Publishers Weekly, and numerous other publications. She writes regularly for The Writer magazine. She is also a Part-Time Professor of Journalism at New York University where she teaches writing and editing courses.

Dearman has developed a wide following as a writing coach. She started seeing private clients and giving workshops in 2003. Many clients came to her through The Writers Room, An Urban Writers Colony in New York City. Dearman went on to curate the Writers Room Reading Series at Cornelia Street Cafe, which also allowed her to nurture and promote the work of local writers. She was also curator of the Homotext Reading Series at Dixon Place, in New York City, where she booked authors Augusten Burroughs and Douglas A. Martin, early in their careers.

Dearman is also an editor, who has worked on staff at Gale Research editing film guides, and freelanced for Simon & Schuster, Silver Moon Press and other houses. She works regularly as a freelance manuscript editor.

Described by many private clients as a down-to-earth mystic, Dearman wrote a nationally-syndicated astrology column for several years. Mademoiselle magazine named her "one the world's greatest astrologers", and she wrote regular columns for Redbook, Ladies' Home Journal, Twist, HX, and other publications.