The aim of this study is two-fold: to discern patterns in pathways of work and family transitions among young women (aged 24–39 years) whose decisions and behaviors toward labor force participation, marriage, and parenthood are considerably shaped by social constraints and gender norms; and to examine whether and to what extent work and family pathways are associated with later health. Using data from a longitudinal survey based on a large sample of adult women in Korea (N = 2418), we identified eight dominant pathways of employment, marriage, and parenthood among young women and found that educational attainment and family values are strong predictors of these work–family pathways. We also found that the timing and sequencing of work–family pathways appears to be associated with later health outcomes. In particular, unemployed women who are not married and do not have children seem to be vulnerable to health problems, compared to those with other pathways. We discuss the implications of our findings regarding the occurrence of work and/or family transitions, as well as their timing and sequencing for women’s health in later life.