The American composer John Cage experimented to step outside the conventional concepts of sound. He employed the Yijing-derived (The Yijing will be used in this chapter, except in Cage’s quotations where “I Ching” were used) chance operations in his compositions to seek for structure and artistic freedom. The liberation from idealism in forms and symbols represents the destabilization of dualism between total control through serialism launched by German-Austrian composer Schoenberg in the earlier half of the twentieth century, and Indeterminacy subsequently explored in both music and performative arts after the 1950s. Cage’s intercultural encounter with the Yijing symbolizes a movement to cultivate simultaneously interfering phenomena. Such simultaneous comprehension of senses can be seen as the representation of the experiential reality, the illogicality that our senses demonstrate. This chapter serves as a case study in analyzing how the first step of Cage's journey into the world of the Yijing as the search for the philosophical concept of the Unity of Heaven and Humanity through sound and music. The pathway to the Yijing can be seen as the continuing expansion from the expression of the incomprehensibility, through the freeing of hierarchies, the collapse of dichotomy, to the exploration of experiential reality already found in experimental music evolved out of the western classical tradition.