During one of Landow's lectures in 1993, Jackson began drawing "a naked woman with dotted-line scars" in her notebook, an image she eventually expanded into her first hypertext novel, Patchwork Girl.

While working in a San Francisco, California bookstore,[5] Jackson published two more hypertexts, the autobiographical My Body[8] (1997), and The Doll Games[9] (2001), which she wrote with her sister Pamela.

In the late nineties, Jackson alternated hypertext work with writing short stories (in publications such as The Paris Review and Conjunctions) and children's books.

Jackson has explained that she "completely ignored" one college professor who told her the key to success was focus, and added that "[s]ometimes this means shuttling manically between art and writing and other, more unmentionable obsessions.

"[2] During this period, Jackson also did cover and interior illustrations for two short story collections by Kelly Link, Stranger Things Happen (2001) and Magic for Beginners (2005).

The novel received mixed-to-positive reviews; Newsweek called it "brilliant and funny,"[12] and The New York Times, while praising Jackson's ambition as "truly glorious," added that "All this razzle-dazzle, all the allusions, [and] the narrative loop-de-loops [get] a bit busy.