This essay examines the dramatization of a new model of selfhood in U.S. naturalist fiction at the turn of the twentieth century and how it was taken up by advice literature during the interwar years. By tracing a lineage of the self through the characterological types of the caveman, genius, artist, and entrepreneur, the essay shows how the construction of the caveman as a more vital self than the bourgeois individual at the turn of the twentieth century morphed into a biologized notion of Romantic genius and further into configurations of artists and entrepreneurs as the century progressed. As the types shade into each other in naturalist fiction and advice literature, they represent a new model for successful working and living that fuses expressive and economic goals, and which anticipates contemporary constructions of work as a pursuit of creative self-expression and self-actualization.