The purpose of this study was to examine the career trajectories of two teachers in the United States and their decision to leave teaching Spanish. Data for the study emerged from the teachers' narratives about their school-based experiences and the consequences of those experiences on their decisions to reorient their work in the educational community. We adopted the theoretical framework of history in person to analyze the interactions between the teachers' own personal histories with the histories of the institutions in which they taught. Data collection began during the two teachers' student-teaching semester and continued for 5 years after their initial induction into the language teaching profession and included interviews and email communications. The context was North Carolina, a state experiencing a severe teacher shortage and conflicts regarding teacher compensation. Findings highlight the challenges these teachers faced and how their interactions with historically institutionalized struggles were consequential to their professional futures. Implications for research, policy, and teacher preparation are discussed.