The general aim of this paper is to present insights from a Polish case study on the learning experiences of Polish older men. The research data was collected by means of ‘guided’, semi-structured interviews. This paper presents two well-educated older men’s life stories from two different local communities in Poland and the analyses of their life experiences in the context of masculinities and ageing using a biographical learning approach. The analyses of the two biographical narratives have shown the diversity in the life histories of older men, but also similar struggles and challenges. They have illustrated how older men cannot simply be reduced to their experience of ageing, but that they also carry some continuously (re)negotiated struggles with masculinity, weaving new and rich threads for learning that is lifelong and life-wide.