Policies to extend working life (EWL) assume homogeneous workers face similar choices about working longer: this may be difficult for women, workers in physically onerous jobs or in low-paid precarious employment. Work-life trajectories are gendered; women interrupt employment and pension-building to provide care. There is occupational variation in capacities to prolong working lives: physically demanding jobs cause work-related health deficits. The precariously employed cannot contribute regularly to pensions and may face age discrimination. This research provides an inter-occupational and cross-national dimension to EWL research, comparing women teachers and health-care workers in the United States of America (USA) and Republic of Ireland. It documents intra-cohort distinctions that emerge among women when considering educational opportunities and occupational tracks expressed in lifecourse trajectories and accumulated capacities for extended work. Analysis draws on interview data from ten teachers and ten health-care workers in each country, comparing the implications of EWL policies for women workers: in precarious versus secure occupations and occupations with different physical demands. It reveals work-life trajectories leading to poorer financial and health outcomes for older health-care workers, especially in the USA. Most women (regardless of occupation or country) opposed extending working life, with concerns ranging from health status and ability to work to the desire to have healthy years in retirement. The most important distinctions are between the occupational categories considered, rather than cross-national differences. Implications for national and work-place policy and research are considered.