In times of rising longevity and shortage of skilled workers, post-retirement work has become increasingly prevalent in many countries. However, not much is known about the expectations and facilitating factors associated with work-related activities after retirement. In two studies we draw on the social cognitive career theory and investigated the role of outcome expectations and facilitating factors in post-retirement career planning. First, we interviewed 22 older employees and subject matter experts in a German aerospace company to learn more about expectations of post-retirement work and its facilitating factors to build a theoretical model. Second, to test our theoretical model, 212 employees of the same company aged 50 to 65 completed a web-based survey. Results showed that outcome expectations and the facilitating factors identified in the interview study were significantly related to post-retirement career intention. Further, the facilitating factor social approval moderated the relationship between outcome expectations and post-retirement career intention. We discuss implications of our findings in terms of how they inform retirement counselors, organizations, and society to help increase engagement in work-related activities after retirement.