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This article reports on a study investigating relationships among the reasons for entry, preparation experiences, workplace conditions, and future career plans of 15 early-career teachers working in urban Los Angeles. Specifically, the authors examine why these teachers stay in, shift from, or consider leaving the urban schools in which they teach. Our analysis highlights the need to reconceptualize teacher retention to acknowledge and support the development of deep, varied, successful careers in urban education. Findings demonstrate that these urban teachers will remain in urban education if they can adopt multiple education roles inside and outside the classroom and receive professional support during the whole of their careers, not just the beginnings of their teaching.