Adults’ work-related learning is of widening interest given concerns about sustaining their employability across lengthening working lives as occupational competence and workplace requirements change. These concerns extend to assisting their workplaces’ viability and ability to provide the goods and services that communities need and, collectively, nation states’ securing their economic and social goals. So, this learning is salient for individuals and the social institutions in which they engage and support. Realizing these outcomes is premised on individuals’ contributions and those social institutions, such as workplaces and tertiary education and communities. So, beyond individuals’ lifelong learning efforts, premised on their capacities and agency, are the educative experiences afforded by workplaces, family, familiars, but also opportunities, guidance and support, and learning experiences found in their communities. Drawing on analyses of the worklife learning experiences of 30 Australian workers, the interdependent and interwoven contributions of person, educational provisions, and community offers explain their worklife learning. Advanced broadly as mediation between personal and societal contributions to that learning, it is proposed that: (a) the societal contributions go beyond intentional experiences in educational institutions and workplaces, to include affordances arising from individuals’ communities, (b) the complexity and variability of those affordances are key mediators, and (c) both personal and societal contributions are salient to working age adults’ learning when navigating worklife transitions.