This study focuses on three new teachers, Arnie, Andrea, and Frank, who are New York City Teaching Fellows (NYCTF), a program of alternative teacher recruitment and certification that is in its third year at an urban public college in New York City. This study focuses on just three of the Fellows in order to have a more intense look into the thinking of new teachers who have made a commitment to teach in poor urban schools for two years and who are now choosing to either remain urban teachers, to leave to teach in the wealthier suburbs, or to leave teaching altogether. The narratives of Arnie, Andrea, and Frank are grounded in three years of continuing research, using interviews and group discussions with a cohort of Fellows to attempt to understand the patterns of thinking of new teachers who are enrolled in a program of rapid certification through full-time teaching and reduced educational coursework. Arnie, Andrea, and Frank articulate four themes which are present in the participants who have for three years been part of this study and who are now faced with making a personal and vocational decision. First, they perceive a lack of continuity between their academic expectations and the perceived lack of academic investment in school culture of a number of their students. Second, this discontinuity is exacerbated by being held accountable to standardized curricula which inhibit the freedom to negotiate both a meaningful teaching practice and a curriculum they see as beneficial for their students. Third, a lack of autonomy negatively influences the kind of vision for professional growth in urban settings that predicts a fulfilling professional and personal life. Last, the importance of personal relationships with their students motivates these teachers to want to remain teaching in difficult situations, and then induces guilt at abandoning those relationships for other professional possibilities.