Abstract We extend research on the “diverging destinies” of children of high- and low-educated mothers by simultaneously considering divorce and employment experiences and by also examining the role of family support and remarriage. Focusing on a sample of ever-divorced mothers in Japan, we demonstrate a strong negative educational gradient in four different measures of economic disadvantage (low income, economic need, subjective economic difficulty, and inability to save). We then show that differences in employment experiences prior to and subsequent to first birth explain part, but not all, of this educational gradient in well-being. Not working and part-time work are particularly important for understanding the relative economic disadvantage of mothers’ with a high school education or less. Finally, we show that access to financial support and remarriage do not account for much of the remaining educational differences in economic well-being. These findings are important in demonstrating how different outcomes central to the diverging destinies framework jointly shape the well-being of mothers (and their children). Biography Jim Raymo is Professor of Sociology and the Henry Wendt III Professor of East Asian Studies at Princeton University. Raymo is a social demographer whose research focuses on documenting and understanding the causes and potential consequences of demographic changes associated with population aging in Japan. His published research includes analyses of marriage timing, divorce, recession and fertility, marriage and women’s health, single mothers’ well-being, living alone, family change and social inequality, employment and health at older ages, and regional differences in health at older ages. His research has been published in leading U.S. journals such as American Sociological Review, American Journal of Sociology, Demography, Journal of Gerontology: Social Sciences, and Journal of Marriage and Family as well as in Japanese journals. Raymo serves on the board of directors of the Population Association of America and is an associate editor of Journals of Gerontology: Social Sciences and Demography. He earned his Ph.D. in Sociology from the University of Michigan in 2000.