Although schools have often served as agents of cultural assimilation, they have also been sites of contestation and transformative change. Despite an increasingly substantial body of literature that addresses the need for teacher transformation, particularly among white teachers, there has been little focus on the process and implications of concientization within specific settings. This dissertation chronicles a participatory, ethnographic study of the lived experience of one English Language Arts teacher dedicated to the more equitable transformation of self and school. Spanning interactions from 2003-2006, but concentrating primarily on her work as the only English teacher in a new program, it details her attempt to redefine practice in more critical and culturally relevant ways and explores the impact of such work on teacher identity. In particular, the emic tropes of the Good Teacher and the Better Student are explored as problematic identity constructions with crucial consequences for teacher-student relationships and pedagogical decisions. Sustained by stratified classrooms and defining achievement in limited ways, they oversimplify the complex set of interactions that necessarily comprise teaching and learning. This study offers a window on transformative practice in process-its inception, its challenges, and its ultimate impact on teacher identity. Specifically, it includes an examination of 1) a teacher's work in two separate school systems-a traditional, comprehensive, suburban high school serving a largely white population, and an alternative, urban Middle College program serving mostly students of color; 2) the power and problems arising from authentic care-oriented classroom relations, and 3) the success and failure of reinvented pedagogical approaches. It argues that, in this case, transformation also creates an identity crisis that simultaneously empowers and destroys, undermining the teacher's sense of self, efficacy, and sustainability even as it inspires her to advocate for marginalized students and to hope for wider social change.