This study examines differences in masculine identity and work identity in a cross-section of men at various stages of the transition to retirement. Masculine identity and work identity refer to how closely one identifies with male sex-role expectations and with one's job, career, and company. The subjects of the study are 50 retirees and 26 workers from one large company that promotes voluntary retirement. These subjects have successfully met societal expectations for men--all are mid-level managers who are socially, maritally, and financially stable. Workers fall into three groups with respect to retirement: those having set no retirement date, those intending to retire in one to three years, and those intending to retire within a year. Retirees fall into two groups: those who have retired within the last year and those who have been retired from two to six years. The study's comparison of the masculine and work identity of men at different stages in the retirement process resulted in several counterintuitive findings: (1) retired men identify more closely with work than workers, maintaining loyalty to their company and pride in their careers; (2) workers who intend to retire in one to three years report more stress in trying to meet male sex-role expectations than other subjects; and (3) the retirees who report greater well-being are those who identify more closely with work.