Focusing on women from the U.S. over 60 years old in 2006, this study analyzed the relationship between retirement and three subjective measures of well-being: depressive symptoms, financial worries, and health. Drawing on the life course perspective and the heterogeneity of women's labor force experiences, this study contrasted the well-being of recent retirees with those who self-identified as homemakers (n = 1695) and long-term retirees with homemakers (n = 2012). Findings indicated that being a recent retiree was associated with more favorable reports of health and that being a long-term retiree was more favorably associated with accounts of all three outcome measures relative to homemakers. Thus, despite the major role change they experienced, findings support the notion that participating in the paid labor force may have been a protective factor with regard to self-assessed well-being.