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Addressing the global challenges highlighted by the UN’s Sustainable Development Goals will require a transformation of systems that created the problems in the first place. Purposefully transforming our societies is difficult, complex, and messy. Innovative change strategies often fail, and there are no general solutions. Even when we have developed promising possibilities, they may falter when we try to scale them upward and outward. The Transformations Community, a global community of action researchers and reflective practitioners, organized a dialogue session on developing transformations support structures which intertwine action and learning, such as Transformation Labs, Co-Labs, Bright Spots, and Learning Networks. In this paper, we present key insights from a dialogue session with some individuals who spent years developing and leading the ‘Pathways’ Transformative Knowledge Network (TKN), an international group working on sustainability challenges in various contexts.