Drawing on an existing typology, this study used latent transition profile analysis (LTPA) to examine changes in the striving and wellbeing profiles among teachers from their early until midcareer. Five profiles were identified (Sparing, Good Health, Ambitious, Burnout, and Wornout) among a longitudinal sample of 414 Australian secondary and primary teachers. LTPA showed that 28% of teachers were movers over time. Most movers from maladaptive types underwent a recovery transition to a more adaptive profile by midcareer, although initial Burnout and Wornout profiles were overrepresented among those who subsequently quit teaching. Perceived excessive work demands and supportive leadership were significant covariates: Perceived excessive work demands decreased the likelihood of transitioning to Good Health or Ambitious profiles; supportive leadership increased the likelihood of transitioning to Ambitious. Profiles were associated with teachers' professional engagement; the Wornout profile exhibited the lowest, and the Ambitious and Good Health profiles the highest professional engagement by midcareer. Implications for theory and policy to support teachers' development and wellbeing are discussed.