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New teacher attrition is among the most salient problems facing the U.S. education system, with recent research attempting to understand this phenomenon in light of the generational characteristics of our nation’s teachers. This mixed methods study examined preservice teachers’ motivations, career expectations, and goals, including their aspirations for working with traditionally underserved populations (e.g., students in urban schools, and English language learners). Findings indicate that, even before officially entering the classroom, many teachers expect to take on multiple and diverse roles during their careers. The paper ends with a discussion of how teacher education might accommodate such differences in teachers’ motivations, expectations, and aspirations in order to promote retention. The findings offer insights for extant theory about teachers’ career paths.