One of the central questions in social science research is what predicts socioeconomic success in adulthood. This article investigates the role of self-esteem and its interplay with social background and intelligence in early adolescence in predicting educational attainment and occupational success in adulthood. Specifically, the present study tests for interactions between these factors and examines whether self-esteem, in particular, has a compensatory or amplifying effect on existing (social) background differences. To this end, it draws on data from the longitudinal study Learning Processes, Educational Careers, and Psychosocial Development in Adolescence and Young Adulthood (BIJU), tracking development from the age of 12 to 31 years. The results indicate a positive interaction effect between self-esteem and socioeconomic background in predicting educational attainment. However, this interaction effect was similarly explained by an interaction between socioeconomic background and intelligence. There were no main or interaction effects of self-esteem on occupational status or income. In sum, at least for educational attainment in adulthood, the results point to cumulative advantages of baseline (social) differences (Matthew effects). These were not specific to self-esteem, however, but were also explained by cognitive resources. No evidence was found for compensatory effects between baseline differences in resources.