Forty years ago, a generation of American women embarked on careers they had never anticipated, knowing almost nothing about what their futures would be like. Now these pioneers are nearing retirement. A lifetime of results are in, and debate is raging about women’s progress, what they can do, what they should do, what hinders them and what remedies to try. We have excellent scholarship on many of these issues, but precious little on what women’s careers actually look like in the long term. We need much better tools to help women envision their futures, clarify alternatives and make choices that will be both viable and right for them over the course of their working lives. This study offers a new model for understanding women’s career development through adulthood. The research is grounded in biographical interviews with 40 women born between 1945 and 1955, from four occupations and a spectrum of socio-economic and ethnic/racial backgrounds. Case histories are used to describe participants’ careers, and to illuminate two life-long developmental tasks: the internal work of forming a vocational identity, and the external work of navigating a career. For women, accomplishing those tasks is complicated by a dilemma imposed by conflicting prescriptions about gender roles—between ambition (choosing a goal and going all-out for it) and drift (taking whatever comes along). Analysis of participants’ responses to the tasks and dilemma over time showed that they followed six career trajectories, distinct pathways that emerged from the astonishing complexity and diversity of their individual histories. Virtually all the women in this study found satisfying careers that exceeded their youthful expectations, even those with floundering beginnings and delayed outcomes. Findings also illuminate the role of confidence in women’s career leaps, and a heretoforeundescribed resource for helping women grow and achieve, the Developmental Community. Implications are drawn for individuals, organizations, research and theory. Acknowledgements: I am grateful to the forty women who so generously shared their life stories for this research. I am also indebted to many colleagues, friends, and family members—above all, my husband, Kelin Gersick—for their thoughtful comments.