We applied a life course perspective to an examination of work-to-school transitions, and highlighted the individual and family-level factors that differentially shape the career pathways of men and women. We employed data from a sample of employed middle-class men and women in dual-earner couples (N = 1,408 couples) to examine the relationship between returning to school and prior educational attainment, individual biographic pacing (age, timing of marriage), job history, current job conditions, psychological resources, and family demands. Results support several hypothesized gender differences in the return to school pathway. Women with the heaviest combination of work and family demands were the most likely to return, an unexpected finding that we discuss with reference to both personal and structural resources.