This chapter assesses Kerouac’s literary career from the perspective of the profession of authorship. Despite his bohemian reputation, Kerouac was a diligent professional writer who engaged publishers directly and via literary agents in order to actively manage his professional career. Kerouac’s goal was to convince publishers and thus the reading public of the significance of his signature artistic style, which he called “Spontaneous Prose.” Viking Press was not interested in his Spontaneous Prose books as viable sellers, and his income and reputation declined in proportion with his insistence on producing books in this style. Despite the belief held by many Kerouac fans today that he was a literary saint who disavowed money and materialism, in fact he both wanted to make money and earn literary respect based on his artistic merits. He was not a commercial writer per se, since he sacrificed publication for the integrity of his art, but he did want the publishing industry to see the inherent value in his Spontaneous Prose books.