Objectives: This research examines whether retirement is associated with mental health and how one's daily pursuits mediate this association. It tests two perspectives from the sociology of work and the sociology of mental health. Methods: Using data from two surveys, the 1995 Aging, Status, and Sense of Control and the 1987-1988 National Survey of Families and Households, regression analysis was used to examine retirement, activities, and well-being. Results: In support of the view that work is alienating and retirement liberating, retirees experienced less anxiety and distress and higher positive affect. Retirees' lower anxiety and distress were explained by activity characteristics. In support of the view that work is empowering and retirement demoralizing, retirement is associated with lower sense of control in both data sets, in part because of the daily pursuits. Retirement was not associated with depressive symptomatology. Discussion: Suggestions for creating opportunities that enhance well-being are discussed.