Womenâ€™s gendered responsibilities of caring for children and the home is persistently identified as a barrier to gender-equal representation in political office. Rather than solely seeking to help women overcome what are often insurmountable barriers, we argue that we also need to align our strategies with womenâ€™s culturally specific life-courses, and the socio-historical conditions of particular cohorts. Drawing upon the experiences of women political actors in Dehradun, North India, we identify post-active motherhood â€“ the stage of life after children are independent but prior to old-age â€“ as an under-recognised moment of political possibility. While women in middleage have the motivation, time and experience to contest elections (supply-side dynamics), the political environment remains hostile to their political advancement (demand-side dynamics). Further, the socio-historical conditions of the next cohort of women political actors, now approaching post-active motherhood are indicative of limited opportunities for political apprenticeship compared to their seniors. We argue for a far-sighted approach to research and practice aimed at increasing womenâ€™s political leadership that analyses and works with culturally and historically specific life-courses for each incoming generation of women political actors.