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).