As the director of Miles Away from “The Cool,” the performer asks me to listen to/for the implications of specific location, the pedagogical potentiality in the life and work of Miles Davis, and his relationship with Davis. The performer asks the audience to consider their subject positions and relationships to and with race, cultural icons, and their pedagogical practices as students and teachers. Together, we want to create a performance that invites the audience to exercise performative reflexivity and listen dialogically. This essay is the director's reflection of this process.