Abstract In this article I analyze empowerment in Copenhagen's “wild” social work community and I develop the role of expansive learning to understand how to transcend marginalization. The notion of expansive activity developed by Engeström and Holzkamp contributes to the further development of Cultural-Historical Activity Theory. I use a social practice theory of boundary communities to analyze empowerment as a dialectic between individual and collective movement. I define boundary communities as communities that overlap two or more groups and thereby offer potential for border crossing and collaboration among communities. I analyze the personal trajectory of a social street worker, Anas, focusing on dilemmas and possibilities for expansive learning. The “wild” social work community to which he belongs is constituted by an overlap of different groups in Copenhagen such as the social street workers, professionals from the “established welfare system,” and local street communities of young men with ethnic minority and Muslim backgrounds. Social street work is analyzed at the time of the street riots that occurred in Copenhagen in February 2008; social street workers facilitated meetings of opposing factions, parties who usually do not enter into dialogue. I discuss how boundary communities may support empowerment of individuals and groups by moving these parties in expansive directions.