This essay reviews and synthesizes Jessie Bernard's writings on women, work, and family. Bernard's conceptualization of “two worlds”—one of women and one of men—provides the organizing theme, from which three major issues are derived: (a) the dilemmas of caring, (b) the feminization of work, and (c) work and family roles over the life course. Examining her historical perspective on these issues, her view of the present, and her vision of the future, the article raises unanswered questions in Bernard's work and suggests implications for future research on women's work and family roles.