We investigate the extent to which people's earlier circumstances and experiences shape subsequent life-courses. We do this using UK longitudinal data to provide a dynamic analysis of employment and caregiving histories for 4339 people over 15–20 years between 1991 and 2010. We analyse these histories as sequences using optimal matching and cluster analysis to identify five distinct employment-caregiving pathways. Regression analysis shows that prior to embarking on these pathways, people are already differentiated by life-stage, gender and attitudes towards family and gender roles. Difference-in-differences estimation shows that some initial differences in income, subjective health and wellbeing widen over time, while others narrow. In particular, those following the most caregiving-intensive pathways not only end up poorer but also experience a relative decline in subjective health and wellbeing. These results confirm that earlier circumstances exert a strong influence on later life-courses consistent with pre-determination, persistence and path dependence.