In this article it is investigated to what extent flexible employment at labour market entry negatively affects the early career of school-leavers in the Netherlands in the period 1986–2008. Additionally, the question is raised to what extent educational differences exist in this relationship. To answer these questions, Dutch panel data from the OSA Labour Supply Panel are analysed. The results correspond with previous findings from studies on other European countries, supporting the stepping-stone rather than the entrapment hypothesis. A flexible start in the Dutch labour market increases the likelihood of repeated flexible employment and unemployment in the early career, and coincides with less occupational status development and income growth. However, the detrimental effects of flexible employment at labour market entry are only temporary and diminish after some years. Furthermore, no evidence is found for the existence of educational differences in the negative effects of flexible employment at labour market entry.