Post-retirement employment has become an increasingly important form of labor force participation for both retirees and employers in the last decade. In order to understand post-retirement employment decision-making, the current study investigates the meaning of work and its relationship to post-retirement employment. Based on previous research, we examined four dimensions of the meaning of work (i.e., social, personal, financial, and generative meaning of work) relevant to predicting post-retirement employment. Population-representative data from the German Transitions and Old Age Potential study ( N = 2,149) were used to test the hypotheses. The results from binary logistic regression analysis indicated that the social and personal meanings of work were positively related to the likelihood to engage in post-retirement employment. Further, subjective economic status was found to moderate the relationship between the financial meaning of work and post-retirement employment. Exploratory analysis was conducted for post-retirement civil engagement and post-retirement family care in order to understand the broader role of the generative meaning of work. The findings of the present study extend previous research on late career decisions. The implications of these findings are discussed in terms of theoretical development and individual and organizational practices.