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. (C) 2016 Elsevier Ltd. All rights reserved.