Pressfield was an advertising copywriter, schoolteacher, tractor-trailer driver, bartender, oilfield roustabout, attendant in a mental hospital, fruit-picker in Washington state, and screenwriter.[2] His struggles to make a living as an author, including the period when he was homeless and living out of the back of his car, are detailed in his 2002 book The War of Art.[2]
Last of the Amazons, in which Theseus, the legendary King of Athens, sets sail to the north coast of the Black Sea inhabited by a race of female warriors (2002), ISBN038550098X
The Profession (2011), ISBN9780385528733. Pressfield's first book set in the future, where military force is for hire everywhere. Oil companies, multinational corporations and banks employ powerful, cutting-edge mercenary armies to control global chaos and protect their riches.
The War of Art: Break Through the Blocks and Win Your Inner Creative Battles (2002), a motivational book that investigates the psychology of creating art and how "writer's block" can be cured. ISBN9781936891023
His novel The Legend of Bagger Vance was made into a 2000 film starring Matt Damon as the golf pro and Will Smith as his spiritual guide and was widely criticized for its use of the "Magical Negro" as a plot device.
Pressfield also appeared as one of the historians in The History Channel's 2007 documentary Last Stand of the 300 and a commentator on an episode of the History Channel's Decisive Battles series featuring Alexander the Great on July 30, 2004.[9]