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This paper examines the career pathways of teacher leavers, individuals who have voluntarily left classroom teaching prior to retirement. Based in the perspective that teachers construct their own career pathways through an ongoing negotiation among personal and professional factors, this research captures the experiences of 24 teacher leavers from across the United States. Using life history interviews, this study inquires into individuals’ experiences before, during, and after classroom teaching. Unexpectedly, none of the participants initially planned to enter education. Data also indicate that teachers’ career pathways were shaped by dynamics of push and pull in entering and leaving teaching. The trajectories of these teacher leavers suggest important theoretical and practical implications for understanding and shaping teachers’ careers in today’s workforce.