In this master thesis, I will look at the transformative nature of the Zhuangzi, and see if, it is comparable to Schilller’s concept of the play drive. Thereby analyzing if there is some sort of common ground between the two. My analysis of the Zhuangzi, will be done through the prism of three different reading strategies of the Zhuangzi. Steve Coutinho’s depiction though the term vagueness. Chad Hansen reading of the Zhuangzi as indexical, and lastly Robert Allinson’s reading though the use of metaphors. Though these different readings of the Zhuangzi, I will point out importance of the playfulness of the writing in the Zhuangzi itself. This playfulness is what I will link together with Schiller’s concept of the play drive and thereby giving it a different level of philosophical understanding.