In this paper, Leonard Waks investigates connections between listening and expertise or mastery, contrasting approaches from Eastern and Western philosophy. The first section accounts for listening in the Daoist classic "Zhuangzi", a work addressing themes in Chinese philosophy through metaphor and story narratives. In one story a character named "Confucius" advises a student to fast the mind and listen recklessly. The affinity between reckless and what has been called "apophatic" listening is demonstrated by the shared feature of mental emptiness - listening without the imposition of conceptual categories. The second section demonstrates close affinities between the account of listening and expertise or mastery in the "Zhuangzi" and in the account of expert perception in contemporary Western philosophy and psychology, as exemplified by phenomenologist Hubert Dreyfus.