This chapter is a critical comparative analysis of the philosophical concept of the art of living (with a focus on Schmid's concept Lebenskunst) and positive psychological research about the good life from an educational point of view. It explores the extent of common ground between positive psychology and some philosophical concepts of the art of living, where they differ and where they might be complementary. The chapter provides significant input for educational considerations such as teaching methods, relevant content and the influence of family and educational settings on the development of autotelic personality traits and experiences of flow. Both Csikszentmihalyi and Schmid, although coming from different angles, reach the same conclusion: the contemporary cultural context plays a major role in the popularity of questions about the good life. The term good life has a multitude of possible readings and interpretations in philosophy, as well as in psychology and in everyday language.