Career decisions of four teachers are explored through the concept of figured worlds in this qualitative, longitudinal case study. Participants were purposefully chosen for similarity at entry, with a range of career trajectories over time. Teacher career paths included remaining in one school, repeated changes in schools, attrition after relocation, and non-renewal of contract. Data included interviews, observations, participants’ assessments, and pupils’ work. Cross-case analysis suggests that no single teacher attribute or workplace condition determined teachers’ career decisions; rather, teachers’ ability to refigure their identity within the figured world of teaching shaped career trajectory. Key factors such as ability to address disequilibrium, teacher identity, agency, and collaborative capacity are examined. Implications call for pre-service preparation and professional development to navigate cultures of schools, amended administrative involvement in teacher retention, and policy reform acknowledging the complexity of teachers’ figured worlds.