In his recent article Philosophy Inside Out, Philip Kitcher presents a metaphilosophical outlook that aims at nothing less than a renewal of philosophy. His idea is to draw philosophers’ attention away from “timeless questions” in the so-called “core areas” of philosophy. Instead, philosophers should address questions that matter to human lives. The aim of this paper is twofold: first, to reconstruct Kitcher’s view of how philosophy should be renewed; second, to point out some difficulties relating to his position. These difficulties concern the integration of his naturalism into the pragmatic vision of philosophy, the role of putative philosophical experts, and the ideal status of the program of well-ordered inquiry.