<p>This article introduces the concept “imagined work-family futures” to examine how young adults’ narratives about their futures shape gender inequalities later in their careers. Drawing on 127 longitudinal interviews with 69 prospective law school students, we show that, at career launch, men and women have equally ambitious aspirations to have high-status careers and to raise children. Yet their expectations—or, their narrated work-family plans and interpretations of probable career scenarios—diverge prior to law school entrance. Respondents articulated one of two expectations about future work-family conflict. Laissez-faire narratives, more common among men, articulate one’s career aspirations as central to one’s current self and work-family conflict as a problem for one’s future self. Deliberate narratives, more common among women, articulate one’s career as inevitably structured by one’s future family and as a problem for one’s current self. Analysis of longitudinal interviews during and after law school reveals that respondents’ expectations remained largely consistent throughout professional socialization, shaping some job choices among women. We discuss how, alongside structural constraints, imagined work-family futures set the stage for future patterns of gender inequality.</p>