Background: Concerns about work-family conflicts are becoming an increasing problem for women administrators. Yet these concerns have been overshadowed in the educational leadership scholarship, which has focused on barriers related to discrimination in hiring and promotion and lack of sponsoring and mentoring. Purpose: To illuminate differences and commonalities in how women administrators from different generations and racial/ethnic identities negotiate work-family conflicts. Research Methodology: A qualitative life course design was employed in this intergenerational study of 31 Black and White women administrators. Main Findings: The participants' efforts to enact the multiple and competing roles of administrator, wife, mother, and caretaker proved to be conflicting across generation and race/ethnicity, especially for women born after the civil rights and women's movements, who confronted a strikingly different gender context than did their older counterparts. To reconcile these conflicts, the participants employed various life course strategies that were distinguished by their unique generational locations and racial/ethnic identities. For example, women in the "older" generation were compelled to prioritize family above professional pursuits more so than women in the "younger" generation. With respect to race/ethnicity, Black administrators relied on extended women kinship ties for child care and household support whereas White administrators primarily sought spousal support. Implications for Research and Policy: Further investigation is needed on the work-family conflicts confronting contemporary women and men administrators. From a policy perspective, there is an urgent need for more employer-supported child and elder care, flexible scheduling, and family-leave policies.