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The purpose of this comparative case study is to better understand how young people’s motivations to teach are developed over time. I compare the career exploration and decision-making processes of 96 academic high achievers attending elite colleges with varying levels of interest and commitment to teaching. I find that intrinsic and altruistic motivations to teach were often developed through social encouragement and feelings of success in teaching-related opportunities, but that few academic high achievers report such opportunities to think about and explore teaching as a career. I also find that extrinsic concerns about teacher pay and prestige took on a heightened significance for academic high achievers, with many attributing this to anxieties associated with elite institutional cultures.