An individual's past, and reflections on it, may influence current and future well-being. Recent qualitative studies suggest retirees' recollections about their careers relate to well-being in retirement. We investigated associations between life course events and subjective career evaluations, gender differences in these associations, and their subsequent association with retirement adjustment. We used data from three waves (2015, 2018, and 2023) of the (NIDI Pension Panel Study (NPPS), a longitudinal survey of Dutch older workers. Using a sample of 6,109 respondents, we used ordinary least squares (OLS) regression models to investigate associations between employment stability facilitators and inhibitors (e.g., promotion, demotion, unemployment) and personal shocks (e.g., divorce, widowhood) and subjective evaluations of satisfaction with the work and family domains of career between genders. Using a follow-up sample (N=4,106), we employed ordinal logistic regression models to investigate the impact of these baseline subjective evaluations on retirement adjustment at follow-up. Employment stability factors such as demotion and unemployment, and personal shocks such as poor psychological health were associated with subjective evaluations of the work and family career domains. Gender differences in these associations were found. Evaluations in both the work and family domains were associated with retirement adjustment at follow-up. Our results demonstrate the importance of life course events on older workers' evaluations of their careers and the long-term impact of subjective career evaluations. Further research is needed to evaluate the predictive utility of these evaluations for other outcomes in older adulthood.