There is a need for art education programs to foster dispositions of reflection and inquiry that inform a critical dialogue about ways in which privilege and power are deeply embedded in educational settings. Helping preservice teachers develop dispositions necessary for navigating the landscapes of learning in educational settings takes repeated rehearsals, returning to the same goals, with a more nuanced perspective. Introductory activities that begin to guide preservice teachers in understanding how lived experiences and biases influence their world perception include: (1) developing a nuanced understanding of self and others; (2) recognizing complicated aspects of the culturally relevant educator; and (3) problematizing sets of experiences based on their own lives. To be culturally responsive means having difficult conversations, over and over, in various forms, making change, and being changed.