This article describes the journey and lessons of a 12-year-long and still ongoing experience of the two authors in working with men at the community level in different parts of India. Starting with addressing domestic violence, the work has proceeded to address issues of power, control and autonomy within the context of deep-seated cultural beliefs and practices, challenging and changing the roles of men both within homes and outside in different institutions. This work has been spread over a number of ‘projects’, most of which remain interconnected, and currently is spread across a number of states in India. In reviewing the lessons from their practice the authors propose a set of precepts or a ‘theory of change’ for working with men and boys to challenge gender discrimination within the South Asian context. To conclude the article, the authors discuss some of the challenges and predicaments in continuing this work within the current development paradigm.