The purpose of this study was to explore how individual and environmental predictors of intergenerational social mobility intersect in rarely studied post‐communist developing society of Estonia. We used a contemporary cross‐sectional dataset (n = 759) to assess the influence of cognitive ability and parental socioeconomic status to the participants’ educational and occupational attainment. Our results indicated that cognitive ability and one’s own educational level mediated the association of parental socioeconomic status with one’s own occupational success. Analysis of separate components of cognitive ability indicated that verbal ability had the highest influence on occupational status. We concluded that both individual‐level and environmental factors have a predictive effect on educational and occupational attainment.