This article reports research funded as part of the recent ESRC Growing Older initiative. The project ‘Family, Work and Quality of Life’ explored changes in economic and social roles across four birth cohorts passing through mid-life (45–59/64 years) in Britain. The relationship between multiple role responsibilities and a range of indicators of quality of life, including material resources, health and engagement in social activities were investigated. The research was based upon secondary analysis of four different surveys: the 2000 British Household Panel Study, the 1994–95 Family and Working Lives Survey, the 1985, 1990, 1995, and 2000 General Household Surveys, and the longitudinal Retirement Survey (1988/89 and 1994). A particularly interesting finding is that being ‘caught in the middle’, in terms of having simultaneous care-giving responsibilities to dependent children and frail parents whilst in paid work, has been atypical. Only one-in-nine British women, and one-in-ten British men, aged 45–49 years (born in 1941–45) occupy all three roles concurrently, but multiple role occupancy is increasing across cohorts, particularly the combination of caring and paid work. Role occupancy significantly affects the accumulation of pension entitlements (particularly second-tier pensions), with the effect that many women who have fulfilled the important social roles of carer and parent will face a low income in old age. Where adverse health outcomes were found, parental role in mid-life was most frequently associated with such poor health, suggesting that continued parental demands in mid-life may have negative health consequences.