This study seeks to examine the implications of student employment for the studies, the entry into the labour market, and social inequalities in higher education. The main argument is that both the quantity and quality of work alongside studies can affect relevant academic and labour market outcomes. On the one hand, high amounts of work may prolong the studies and decrease academic achievement. Side-jobs during studies may also distract away students from continuing on in education. On the other hand, jobs of better quality—such that provide experience and skills that are important for the future career—may enhance the transition from education to work. Most important, student employment may generate inequalities in the higher education system if the advantages and disadvantages of working are unequally shared among social groups. The study investigates these issues by using rich longitudinal data on the education and employment history of Bachelor’s students in Germany, by looking at various facets of students’ jobs, and by applying methods that aim at proving causality.