The distinction between adaptive and transformative capacities is still not well understood, and in this study we aimed to build a transformative learning space to strengthen transformative capacities. We proposed that two capacities will be essential to transformation: the capacity to navigate emergence and cross-scale systems reflexivity. We outline our efforts to design and deliver a Global Fellowship program in social innovation, intended to strengthen these two capacities among practitioners already engaged in socially innovative work. Results indicated that the concepts, frameworks, and experiences introduced through the Fellowship led to four key insights about these capacities. Firstly, individual Fellows and their organizations were able to see some complex system dynamics that were previously invisible, which in turn, allowed Fellows to see the distribution of resources and agency across the system in new ways. Secondly, engaging with diversity is essential in social innovation and transformative change processes, and system reflexivity aided in doing this. Additionally, Fellows indicated they were able to identify different kinds of opportunities and the generative potential that can lie within social-ecological systems. Lastly, the findings demonstrate the challenging nature of crossing scales and how a transformative space, such as a Fellowship, helps to practice the experience of contestation, unpredictability, and the uncontrollable dynamics of transformation and social innovation.