A central task for sustainability science in the Anthropocene is to offer guidance on alternative pathways of change. Even though this search and implementation of pathways towards sustainability is likely to require profound social-ecological transformations, little is yet known about the individual and collective capacities needed to support such transformations. This thesis explores the connection between human imagination and sustainability transformations, and introduces the notion of the transformative imagination to support methodological innovation in sustainability sciences, and practices aiming to support transformations towards sustainability. The transformative imagination is suggested to support fundamentally new ways of seeing, feeling, encountering and envisioning the world. The thesis takes a transdisciplinary action-research approach and studies how specific participatory practices, including the arts, may foster the transformative imagination as a means to more skilfully respond to, anticipate and shape social-ecological trajectories in the Anthropocene. The four included papers, each explores how practices may support particular features of the imagination as a transformative capacity. Paper I analyses a case in coastal Kenya where participatory modelling and future scenarios are applied to foster imagination of dynamics of interdependences and trade-offs within the context of poverty alleviation and ecosystems change. Paper II explores system diagrams and scenarios as practices for the development of social-ecological narratives that may support robust interventions in coastal Kenya and Mozambique. Paper III implements, and studies how an art-based approach based on performances, visual methods and an art installation, could support transformative visions of the Iberian Peninsula in the context of extreme climate change. Paper IV is a literature review of the potential contributions of the arts to transformations, in the context of climate change. These papers focus on different features of imagination, which under certain circumstances may progressively develop into societal transformative capacities with the potential to re-structure current social-ecological realities. Overall, this thesis is a step towards forging new kinds of reflexive, imaginative and deliberative practices that can support the emergence of local arrangements of a sustainable world where life can carry on.