This paper discusses the school, work and marriage trajectories of young people in Ethiopia, drawing on qualitative longitudinal data gathered from 30 young people and their parents, and descriptive survey statistics. It contributes to the global debate on the linearity of transitions and seeks to establish whether gender plays a role in shaping young people’s trajectories. The key findings include that children developed high educational aspirations and tried hard to achieve them, though often with little success. Poverty, work, illness, family-related problems, and (for girls in particular) early marriage had cumulative negative impacts, eventually forcing them to leave school. Furthermore, the transition to marriage affected young women and men differently, and getting married prior to finishing education curtailed the ambitions of some girls as they became housewives, fully dependent upon the income of their husbands. These findings challenge the normative understanding of ‘transitions’ by suggesting that they are neither clear-cut nor a one-off or one-way process. In Ethiopia, where poverty and strong social norms shape the majority of children’s lives, their trajectories appear to be interconnected and overlapping, rather than distinct pathways. Finally, the paper highlights some policy implications, calling for comprehensive childfocused social protection interventions to reduce the negative impacts of both poverty and gender on young people’s trajectories