To investigate the development of self-esteem in the early work career, a secondary analysis of data from 843 members of the “Youth in Transition” panel of young men was performed. Maximum likelihood structural equation techniques were used to estimate a causal model including socioeconomic background and ability, self-esteem one and five years following high school, and work autonomy, education, income, and occupational prestige five years after high school. Supporting Rosenberg's “principle of attribution” and Kohn and Schooler's “generalization model,” the experience of autonomy at work was found to have a significant positive effect on self-esteem. The findings suggest that conditions of work are more consequential for the self-image than socioeconomic standing. This study contributes to the growing evidence that persons respond similarly to experiences of autonomy in work, irrespective of age.