This study addressed a gap in the literature by examining the role of core self-evaluations as a predictor of retirement preparation (i.e., attitudes, expectations, and goals), compared to other important aspects such as demographic, financial, health, and work-related variables. Based on the resource-based dynamic model for retirement adjustment and the core self-evaluations theory, the present study showed that core self-evaluations significantly and positively affected the social component of retirement adjustment (H1), the retirement expectations of new beginning (H2), the retirement expectations of continuity (H3), and retirement goals (H4). Additionally, core-self evaluations negatively affected the retirement expectations of imposed disruption (H5). All the analyses were controlled for age, gender, perceived health, financial situation, job centrality, and expected retirement age. In conclusion, core self-evaluations are valuable and supportive to workers across the work lifespan, and for dealing with the retirement preparation.