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The aim of the study was to explore the well-being trajectories of adaptation to retirement in relation to individual and cultural differences, with a particular focus on gender. The sample consisted of 596 retirees (330 German, 266 Polish, 59% female) assessed four times within 12 months. Subjective well-being was evaluated with a multivariate approach that accounted for satisfaction with life, depression and subjective health. As potential correlates of well-being trajectories, age- and context-relevant psychological resources were examined, specifically, generalized self-efficacy, meaning in life, autonomy, religiousness and Schwartz’s values. Latent class growth curve modelling revealed four trajectories per well-being domain. After cross-tabulation, two groups that constantly had the best and worst well-being profiles were identified. One group mainly comprised German men, and another mainly comprised Polish women, who additionally reported the least pronounced socioeconomic and psychological resources. The main predictors of group membership were self-enhancement values (power and achievement), which were higher for the worst well-being group. These values may compensate for a lack of relevant psychological and social resources. Further studies are needed to examine whether this effect is observable in other socially disadvantaged groups.