Individuals in their mid-thirties are expected to be employed and economically independent. However, people with disabilities and health problems--for example, former students with special educational needs (SEN)--may have problems in this domain of adult life. In Norway, individuals with SEN frequently rely on social security and support measures from the Norwegian Labour and Welfare Administration (NAV). This article is based on the narrative analysis of life course trajectories of seven young adult males over a period of 17 years--from their enrolment in upper secondary school with special needs teaching whilst in their teens to their participation in various NAV programmes whilst in their mid-thirties. The life course approach, with an emphasis on transitions and trajectories, has been used as the theoretical framework for analysing the presented data. The hope is that, taken together, these seven stories provide a deeper insight than one individual story could offer. We find that both social structures and the earlier life course affect one's opportunities for joining the labour market.