Social, political, epidemiological, and economic forces have produced family instability during childhood for many young people transitioning to adulthood in South Africa. This study identifies pathways to adulthood for youth in Cape Town that capture the timing and sequencing of role transitions across the life domains of school, work, and family formation. It then uses these pathways to investigate the relationship between childhood family instability and the way young people’s lives unfold during the transition to adulthood. Results indicate that changes in co-residence with parents are associated with following less advantageous pathways into adulthood, independent of particular family structure or orphan status. Overall, the findings suggest that family instability influences not only single transitions for youth, but also combinations of transitions. They also indicate the value of a multi-dimensional conceptualization of the transition to adulthood in empirical work.