This paper contributes to a body of work which examines how women’s work orientations and evaluations of their paid work change over the life course. We analysed interview transcripts for a sub-sample of 110 women drawn from the National Child Development Study (1958 British birth cohort). The paper focuses on retrospective evaluations of the working lives of women who entered the labour market with an instrumental work orientation from the vantage point of mid-late life. Our findings indicate that some women found more intrinsically satisfying paid work later in their working lives, in some cases after gaining additional qualifications. Women also identified barriers to attempting shifts in work orientations. The results show the dynamism of women’s labour market trajectories in late mid-life and highlight the interest of studying women’s changing work orientations throughout the life course.