This article aims to deepen understanding of the trajectories through school and into adulthood of people who did not attain valued qualifications from upper secondary school (‘non-completers’), and explore the fruitfulness of careership theory for such analysis. It is based on interviews with 100 young Swedes: 81 non-completers and 19 who had attended special upper secondary schools catering for young people with mild cognitive disability. Their narratives portray sparse socio-economic resources and difficult family situations, learning problems and marginalisation processes in school. They commonly learned to perceive themselves as failures and ‘different’. Framed by narrow horizons of action, these young people’s careers were mostly characterised by enforced rather than self-initiated turning points. Often leading to unemployment and economic problems, leaving secondary school was less of a turning point than a continuation of failure, even if completing adult education and getting a job were regarded as self-initiated, positive shifts. We conclude that careership theory was useful for analysing and understanding the careers of the young people concerned. However, distinguishing between ‘routines’ and ‘turning points’ became especially difficult when studying lives of these young people hemmed in by sparser resources, fewer choices and less stable career trajectories than their peers.