The idea of happiness boomed in the public as well as in the academic domain over the last decade and has not reached its peak yet. However, the understanding of happiness (understood as eudaimonia) as being the utmost goal of human beings is hardly new. Philosophers have discussed this topic, under various terms, throughout history. One of the most recent philosophical concepts has been conducted by Wilhelm Schmid in his book Philosophie der Lebenskunst [Philosophy of the Art of Living], which is a theory about the good and beautiful life from a modern perspective under consideration of the philosophical history of this topic. Martin Seligman presented the ‘happiness formula’ in his book Authentic Happiness in 2002 and research about happiness, subjective well-being and life satisfaction (among others) began to form the field of positive psychology. This article provides a critical comparative analysis of philosophical concepts of the art of living and positive psychological research from an educational point of view. I t will explore the extent of common ground between these disciplines, where they differ, and where they might be complementary.