This article examines the career histories of the first generation of UK women to enter professional employment in the 1970s and 1980s in comparatively large numbers. In so doing it contributes to the sparse literature on older women’s working life histories. Presenting empirical research on women’s experiences in the legal and HR sectors, it reveals how women pioneers were often silenced by requirements to conform with male-dominated norms, values and practices governing masculine career pathways. They learned to speak a predominantly masculine language that in turn constituted a significant barrier to effective resistance and disallowed new ways of speaking about careers. The article argues that these earlier conditions of entry into careers continue to influence the barriers women face at work today. Through this analysis of older women’s working lives, the article also contributes to contemporary debates about intersectionality by illustrating how gender and age interact in ways that reinforce earlier patterns of career disadvantage.