This paper examines and defends a conception of the education of emotions found in the Zhuang-Zi. I begin by exploring four principal features of Zhuang Zi’s philosophy as it relates to the emotions: his epistemological perspectivism, his view of the self, his ethics of wandering and natural spontaneity, and his playful non-seriousness. Together these four features allow us to discern a general orientation to the education of the emotions, including a normative account of a good emotional life as well some suggestions for a pedagogy for the development of such a life