The article analyses gender differences in the work values of two educational cohorts. A longitudinal research project studied the value judgments of the high school graduates from 1966 until the year 1991 and the high school graduates from 1983 until the year 2004. The analysis proceeds from a three-part structure of work values based on different motivating outcomes or the expected benefits derived from work introduced Rosenberg. Self-expression oriented values refer to the opportunities for self-expression that accompany the accomplishment of one’s work tasks. In the longitudinal study of the educational cohort from 1983 people with higher education ranked these values higher. The post-Soviet period saw a significant increase in the self-expression oriented values among women. Heterogeneous instrumental values refer to the benefits derived from work. They are closely associated with masculinity and men rank them higher. Men’s higher rankings of professional career and social position depended on both education and social factors. Similar evaluations of the recognition of friends and acquaintances did not depend on the level of education but on the social atmosphere. Women, regardless of age, education of social order valued the cleanness and physical ease of work more than men. Social values refer to benefits oriented towards other people and relationships. Regardless of education, age or social order, women valued them more than men. The gendered differences were the greatest in connection with the value of altruism among the respondents with higher education. The comparisons of educational cohorts demonstrated that education and social changes were more important factors in determining values than age.