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This paper explores the challenges of starting one’s career as an urban schoolteacher. Many who begin their career wanting to teach urban schools have not spent time in this setting and have little knowledge about the experiences of urban children and youth. This lack of experience challenges the construction of a professional identity. Misreading cultural cues, facing unexamined assumptions, grappling with questions of self-confidence, all contribute to the novice’s journey to become a teacher. The paper draws on the work of five novices teachers and shows how in predictable ways the happenings of urban school life challenge them. The paper shows how context impacts professional identity formation and concludes with implications for preparing and supporting teachers for the urban school.