In recent years, interpreters of the fourth century BCE Chinese Daoist text, the Zhuangzi, have increasingly appropriated the term, 'skepticism' as a label for the philosophical contribution of that text to classical Chinese philosophy. Despite their terminological agreement, these authors differ significantly in what they take to be the substance of this philosophical term, especially in its context as an interpretive device for understanding the Zhuangzi. This dissertation aims to understand the philosophy of the Zhuangzi by reference to the Greek (...) tradition of Pyrrhonian skepticism transmitted to the modern age by Sextus Empiricus. ;I illustrate the limitations of interpreting skepticism merely as negative dogmatism and illuminate the virtues of understanding it as the recommendation of a philosophical attitude of non-assertion and open-mindedness. Robert E. Allinson, Philip J. Ivanhoe, Bryan W. Van Norden, and Chad Hansen interpret skepticism as an anti-intellectual negative dogmatism, and I take issue with the appropriateness of such an interpretation. In so doing, I examine the work of A.C. Graham, Paul Kjellberg, and Lisa Raphals, who understand the skeptical sections of the Zhuangzi as recommendations for living a fulfilling life. These thinkers offer more coherent interpretations in so far as their readings construe Zhuangzi's skepticism as supporting rather than conflicting with the passages that advocate a variety of spiritual practices designed to bring about peace of mind and harmony. While these interpreters have drawn attention to the importance of Zhuangzi's spiritual and moral recommendations for living a productive life, my analysis, in suggesting that Zhuangzi moves from non-dogmatic or aporetic skepticism to way-making , develops this positive result of Zhuangzi's non-dogmatic skepticism further. This positive result is explored in connection with the extent to which non-dogmatic skepticism can serve as a foundation for the adoption of an attitude of philosophical pluralism, which suggests that there are a plurality of different standpoints, attitudes, approaches, perspectives, and 'positions' each of which may be valid in some sense and in some degree, and yet none of which is immune from criticism. I also address the criticism of aporetic skepticism that living a life without dogmatic commitments is impossible. (shrink)