Beginning with an anecdote from the Zhuangzi about a wheelwright who is unable to pass on his knack for wheel-making to his son, this article goes on to argue that the process of teaching and learning in this context should not be understood as one of transmitting knowledge but instead as one of cultivating habits. According to Zhuangzi, learning does not mean attaining truths given to one by another, but means familiarizing oneself with concepts by applying them in different situations. To clarify these arguments, I compare Zhuangzi's position to that of Wittgenstein, who I attempt to show has similar views on teaching and learning. Most significantly, I argue that both Zhuangzi and Wittgenstein see language as logically and phenomenally groundless, and that this view influences their endorsement of exemplification and practice over explanation and definition with regard to meaning and understanding. Given their perspectives on language and practice, any pedagogical process developed from the philosophies of these two thinkers would not be concerned with imparting knowledge or principles but with cultivating skills through emulation and habituation. Consequentially, before teachers can actually teach efficiently, they must themselves possess habits appropriate to what they are teaching.