The composer, author, and teacher, John Cage, was exercised by our 'inability' to truly listen when approaching sound. In exploring the influences on Cage's avant-garde style, specifically the spiritual discipline found in both Zen Buddhism and Chance operations, this paper attempts to distinguish his philosophy (and use) of "silence" and "chance" as an aesthetic pedagogy. In accordance with Dewey's aesthetic theory and Shusterman's Somaesthetics, resolving the inability to listen is aesthetically conceived as somatic 'attuning' to the occurrence of chance sounds in the ambience of the world. By maintaining Cage's spiritually informed approach as a compositional framework, this paper highlights how his philosophy of silence is pedagogically illustrative of the "active" engagement we can have with the world. This approach is most apparent in Cage's "4'33"," where the 'musicalizing' of everyday sounds erodes the boundaries between art and life, creating a continuity with the world. Somewhat problematically, Cage attempted to make this possible by channelling experience into a state of immersion, unifying art and life by 'letting go' of subjectivity. But as is shown by the Fluxus artists who were inspired by Cage's teachings, the possibility for negotiating Cage's terms brings with it an opportunity to theoretically reflect on the educational processes that underpin Cage's approach to sound.