In his path-breaking monograph, Class and Conformity, Melvin Kohn reasoned that parents prepare their children for the same conditions of work that they themselves experience. Kohn and his colleagues’ research focused on the influence of parental self-direction at work on parental child-rearing values and practices, as well as the self-directed values of children. The intergenerational transmission of occupational self-direction from parents to the succeeding generation of adult children, strongly implied by Kohn’s analysis, has not been empirically tested. Using two-generation longitudinal data from the Youth Development Study (N = 1139), we estimate a structural equation model to assess the intergenerational continuity of occupational self-direction. We find evidence supporting a key inference of Kohn’s analysis: that self-direction at work, a primary feature of jobs of higher social class standing, is transmitted across generations via self-directed psychological orientations, operationalized here as intrinsic work values. Intrinsic values also significantly predicted second-generation educational attainment, contributing further to the reproduction of socioeconomic inequality. The findings enhance understanding of the intergenerational transmission of advantage.