This article presents a study of the occupational careers of men and women born between 1850 and 1922. First, we test the claim that since the mid-19th century individuals increasingly had successful careers. Second, we test hypotheses on differential career success derived from resource theory as well as from a norms and societal expectations framework. Successful careers are defined as starting at a higher level of occupational status and as growing in status at a faster rate. We consider (i) the influence of time-constant as well as time-varying characteristics on individual careers; and (ii) whether these effects changed over time. The Historical Sample of the Netherlands provides multiple measurements of the occupational status for 1,407 men and 824 women. The results show that there is hardly any trend towards increasing career success. For men, resources played the most important role for career success (e.g. basic schooling, father’s class and being married), whereas for women the findings were more mixed. Over time, sons of skilled workers had less successful careers. This suggests that it came to a reshuffling of advantages in the labour market rather than an improvement of occupational chances for all social classes.