Peter Mendelsund often says that “dead authors get the best book jackets.”

Mr. Mendelsund, who has designed striking covers for departed literary giants like Kafka, Dostoyevsky, Tolstoy and Joyce, dreads working with picky writers who demand a particular font, color, image or visual theme. “It ends up looking like hell,” he said.

Then last year, Mr. Mendelsund, the associate art director at Alfred A. Knopf, became his own worst nightmare. He started writing a book himself. Coming up with a cover for his book, “What We See When We Read,” a playful, illustrated treatise on how words give rise to mental images, was excruciating, he said. As the author, he felt as if no single image could sum up the book’s premise. As the jacket designer, he had to put something on the front, or resign in disgrace. His first attempt was stark and off-putting: a plain black cover with small white text. “It was like stage fright,” he said. “I just seized up.”

Stage fright isn’t a chronic affliction for Mr. Mendelsund, a 46-year-old “recovering classical pianist” who taught himself graphic design. More often, he suffers from a surfeit of ideas. In the past decade, Mr. Mendelsund has designed about 600 book jackets, ranging from a sober, sophisticated cover for Tolstoy’s “War and Peace” to his whimsical Pop Art-like treatment of Kafka’s novella “Metamorphosis,” to the hypnotic fluorescent swirls on Stieg Larsson’s thriller “The Girl With the Dragon Tattoo.”

Mr. Mendelsund has long been regarded as one of the top book designers at work today, taking his place alongside design luminaries like Chip Kidd, Alvin Lustig and George Salter. Now, he’s making his debut as a writer, with two books coming out next week. Both explore the peculiar challenges of transforming words into images, and blend illustrations with philosophy, literary criticism and design theory.