The primary aim of this three-wave 10-year follow-up study was to investigate the intra-individual change trajectories of job-related affective well-being among Finnish managers (n= 402). Job-related affective well-being as indicated by anxiety, depression, comfort, and enthusiasm was measured in 1996, 1999, and 2006. The characteristics of the trajectories were sought from experienced career disruptions (i.e., periods of unemployment or lay-offs) and perceived job insecurity. The growth mixture modelling (GMM) revealed altogether three latent trajectories that differed from each other in their mean levels and regard to changes in job-related affective well-being over time: (1) high and improving well-being (n= 347), (2) decreased well-being (n= 32), and (3) low and improving well-being (n= 23). The associations between job-related affective well-being trajectories and career disruptions depended upon the timing of the career disruptions. In addition, perceived job insecurity is associated with concurrently decreased occupational well-being. Overall, the results highlighted both typical and untypical development trajectories of job-related affective well-being and related career characteristics.