This paper documents results of research regarding one pre-service educator’s motivation to remain in the teaching profession at the secondary level. This qualitative research was based on semi-structured interviews and collaborative analysis between researcher and pre-service educator that included an iterative process of theory building informed by a pre-espoused theory treated as a secondary source of data. We present an instrumental case examined through the lens of self-determination theory (SDT), a theory of motivation shown to successfully inform a wide array of psychological data concerning human behavior and optimal functioning in a variety of social contexts but that, nonetheless, remains underutilized in the field of education. Applying this theoretical lens, we document the struggle that early educators may experience as a result of the felt loss of autonomy and volition with respect to the pedagogical competencies that teacher preparation programs help to instill. We provide recommendations for both teacher educators and school administrators hoping to secure educator success and retention in schools operating under strong teacher accountability mandates. We argue that self-determination theory is a powerful conceptual model that may inform and predict the experiences of others like our instrumental case subject working in similar environments, with our ultimate motive being the better preparation of aspiring educators’ in terms of their pedagogical savvy regarding professional realities.