Parents' educational attainment is generally completed before offspring are born. Thus, there is little opportunity to study the ways in which children's observation of their parents' pursuit of education may augment the effects of structural factors on intergenerational transmission processes. In this article, the authors use qualitative and quantitative data collected from thirty-five women across a decade following their return to school to examine the effects of children's observations of their mothers' educational achievements on the children's educational aspirations and achievements in adulthood. The return to school was consequential only when mothers completed their degrees; when they did not, their enrollment appears to have had little or no effect on children's educational achievements. Mothers' completion of college was found to be the most important for children's educational outcomes when fathers were less educated and opposed to mothers' enrollment and when the return to school was fueled by personal and psychological, rather than career, motivations.