Securing the kinds of learning across working life to sustain employability is of growing interest to governments, workplaces, professional bodies and workers themselves. Beyond individuals’ lifelong learning efforts, premised on their capacities and agency, and the deliberate engagement in educative experiences afforded by workplaces, family, familiars, and educational institutions, are also the opportunities, guidance and support, and learning experiences under their communities’ auspices in realising those outcomes. Hence, a combination and interdependence of working age adults’ learning efforts (i.e., lifelong learning), the provision of organized educational experiences (i.e., lifelong education) and engagements with and support of the communities are central to understanding and realising how adults’ work-related learning progresses across working lives. Drawing on the responses to a survey of over 670 working age Australians, this chapter advances further the findings from the worklife histories and narratives of over 60 interview informants in which the distinct but interdependent contributions of individuals (i.e., person), education (i.e., educative experiences), and community (i.e., opportunities, support, and guidance) mediate these individuals’ worklife learning. This chapter identifies whether and in what ways these contributions are applicable to a broader population of working age Australians and how they align with securing the kinds of worklife learning to sustain employability.