The central aim of this article is to explore the role of social enterprises in relation to providing a space for dialogical learning amongst people with different backgrounds and cultures, and hence with different perceptions towards community development practice. The case studies are based on the experiences of the Japan Workers' Co-operative. The study aims to explore mutual-learning processes amongst multi-stakeholders, including a recent attempt to work together with the socially disadvantaged. Through the analysis of "associated work" with multi-stakeholders in the local community, the focus is particularly on its challenging attempts to create various co-working circumstances amongst worker-members, clients, and the local community to raise a sense of community consciousness, thereby implying the potential of dialogical community learning as central to the holistic community development practice with a more collective and socially subjective nature.