Drawing on nationally representative data collected for two age cohorts in the UK, this paper a) assesses the effect of multiple independent socioeconomic risk factors in shaping the transition from school to work; and b) identifies potential protective factors enabling young people to beat the odds. By comparing experiences and findings across two cohorts we assess the generalisability of findings across contexts, i.e. the 2008 and 1980s recessions. The results show that some young people exposed to even severe socioeconomic risks avoid being NEET (not in education, employment or training). Factors that appear to reduce the cumulative risk effect in both cohorts include prior attainment, educational aspirations and school engagement, as well as the social mix of the school environment.