This thesis is a fictionalized personal essay about a year of cross-cultural teaching career in an urban setting. It is a reflection on the ways in which race, culture, and language play into efforts to teach constructively and relevantly in a multi-age, arts-integrated, middle-school classroom. It is a personal narrative about the internal troublings white teachers face in light of race, class, and citizenship privileges—as well as in light of an under-funded urban school system. This essay involves fictionalized vignettes of crisis inside and out of the classroom and provides opportunities to reflect on the ways theorizing and action are intertwined in teaching practice and educational research, and to expose the importance of critical reflection in efforts to teach toward equity and justice. Founded upon a dense literature review within the fields of curriculum and teacher preparation, this thesis magnifies the metaphoric and pragmatic lenses through which we examine culture in classrooms, texts, schools, and educational institutions.