This 2020 volume brings together philosophers and psychologists to investigate the phenomenon of transformative change and a host of fascinating questions it prompts. Taking their departure from seminal work on transformative choice and experience by L. A. Paul and Edna Ullmann-Margalit, the authors pursue fundamental questions concerning the nature of rationality, the limits of the imagination, and the metaphysics of the self. They also strike out into new areas, including value theory, aesthetics, moral and political philosophy. Several chapters present the results of experimental investigation into the psychology of transformation, self-concept, and moral learning.