This paper examines the conceptual matrix of philosophical counseling, and philosophical practice generally, which distinguishes philosophical practice from mainstream theoretical philosophy. I argue that the essence of philosophical practice is the realization and radicalization of Pierre Hadot’s paradigmshifting view of ‘Philosophy as a Way of Life,’ through the projection of philosophical concepts and methods to the goal of attainment of the good life by moral education and character-building. The base-line concept of the good life that the paper works with is the relatively uncontroversial concept of a life based on sustained reflected pleasures that are both socially desirable and individually fulfilling. I argue that this type of con...