The classical Chinese philosophical tradition (ca. 6th to 3rd centuries BCE) contains rich discussion of skill and expertise. Various texts exalt skilled exemplars (whether historical persons or fictional figures) who guide and inspire those seeking virtuosity within a particular dao (guiding teaching or way of life). These texts share a preoccupation with flourishing, or uncovering and articulating the constituents of an exemplary life. Some core features thought requisite to leading such a life included spontaneity, naturalness, and effortless ease. However, there was also significant disagreement during this ‘Warring States’ or ‘Hundred Schools’ period on which skills were valuable, how one should cultivate them, and who exactly ought to serve as exemplars. In this chapter, I discuss two prominent types of expertise and their attendant skills. The first is expertise at a particular craft, occupation, or dao, which finds its most poignant celebration in the early Daoist anthology Zhuangzi. Interest in crafts or skilled occupations was likely motivated by a perceived (or implied) analogy with living a good life more generally. The second concerns ethical expertise, a prominent and widely held ideal within the Ruist (Confucian) and Mohist schools. Both maintain that ethical expertise consists of an ability to apply past models or precedents to current cases, though they diverge on what those models are and how to properly apply them. The aim is to provide non-specialists an overview of this literature in Daoism, Confucianism, and Mohism, while also providing suggestions about further research.