By applying a lens that combines insights from the literature on multiplicity of entrepreneurship forms, cross-scale interactions, and opportunity contexts to the social innovation histories of this book, this chapter provides some key insights on transformative agency and identifies possible areas for future research. It highlights the accumulated, collected quality of individual, often intergenerational, agency interacting over long time periods and shows how the combined strategies of change agents form a system entrepreneurship that is crucial for achieving large-scale, transformative change. The chapter also shows how different opportunity contexts require different strategies and reveals that the ability to change strategies when the opportunity context changes is crucial. This ability is an important part of the capacity to navigate transformations. These insights on the role of agency and opportunity can help increase the pace of social change and contribute to achieving important transformations needed to deal with the current global challenges.