This study asserts a theoretical model of academic and work socialization within the family setting. The presumed associations between parents’ work valences, children’s work valences and valence perceptions, and children’s academic interest and achievement are tested. The results suggest that children’s perceptions of parents mediate the relationship between parents’ and children’s self-reported work valences and children’s work valences are, in turn, associated with academic interest and achievement. The results also demonstrate the moderating role of gender, with an indication of parental socialization to work occurring within same-sex parent–child dyads that is not reflected in cross-sex dyads. Implications and limitations of this study are discussed with a special emphasis on the relatively weak association between parents’ self-reported work valence and their children’s perception of them.