I examine how midlife women, who came of age in the 1950s, compare their career accomplishments with those of their young adult daughters who came of age in the 1970s. Analyses are based on quantitative and qualitative data from the Wisconsin Longitudinal Study, which has tracked a sample of adults since their high school graduation in 1957. Nearly two-thirds of the mothers report that they have been less successful than their daughters; yet these unfavorable comparisons are linked only weakly to self-esteem. The open-ended interviews suggest that the mothers who rate themselves as "less successful" than their daughters maintain positive self-evaluations by characterizing their own decision to give family responsibilities priority over career pursuits as "in step" with their cohort peers; by attributing their less successful careers to cohort differences in the freedom to choose one's career; and by focusing on their daughters' difficulties in balancing work and family demands. (Contains 1 figure, 9 footnotes, and 5 tables.)