This article explores the pedagogical implications of John Dewey's claim that his definition of experience is shared by Daoists. It compares characteristics of experience with those in Daoism, and then considers the similarities and differences between key cultivation practices each proposes, focusing on the roles of the teacher and sage. My main reference to Daoism is the translation of the "Daodejing" by Roger Ames and David Hall, who use Dewey's conception of experience to explain the character of Daoism. There are two facts that Dewey chooses to define experience and link with Daoism--what it is not, and what it is. Comparisons of these facts with Daoism support Dewey's claim: both define the "what is" as the principle of unity of opposites. While sharing this view, their proposals for its cultivation reveal similarities, but also some significant differences. The "Daodejing" gives the Daoist sage a major role to play in the cultivation process of other persons, as does Dewey for the teacher. However, unlike Dewey's teacher who guides the process, the sage is to create a cultivating environment, thus allowing the sage to "let go." The Daoist practices offer new ideas to consider in the quest for experience in lessons.