Transformative learning (Mezirow 1978) is gaining increasing attention in research on sustainability education and on the learning of adults while striving for sustainability transitions. While, as Singer-Brodowski (2023) argues, this theoretical perspective holds strong potential to address under-investigated aspects of education and learning in the context of sustainability issues, its attention for transformation of deeply held and emotionally invested assumptions about the world and oneself and for learners’ capacity to (collectively) contribute to societal change is not unique. Also, other traditions in educational/learning theory such as social learning (e.g. Wildemeersch & Vandenabeele 2007) and Argyris and Schön’s (1978) theory of single- and double-loop learning have addressed this. This paper focuses on how the long-standing tradition of pragmatist educational theory and in particular the application of Dewey’s transactionalism in didactic research (Garrison et al. 2022) has addressed the topic. We explore what pragmatist theory and transactional analytical methodologies have to offer and how this can complement transformative learning theory to deepen our insight in transformativity in learning processes. The paper elaborates three theoretical and analytical principles and discusses their potential for investigating transformativity. First, we discuss the central concept of ‘transaction’ (Dewey & Bentley 1949) – distinguishing it from self-action and inter-action – with its emphasis on how persons and their environments transform simultaneously and reciprocally through a continuous, dynamic interplay between intrapersonal aspects and aspects – interpersonal, institutional, and material – of the environment. Second, we explain how a pragmatist approach to the phases of habit, crisis, and creativity that mark human action (Shilling 2008) results in a focus on the disturbance of habits and customs as a crucial driver for learning and, potentially, for the (trans)formation of behaviour, assumptions and societal systems (Van Poeck & Östman 2021). Third, we emphasise the value of detailed empirical investigations of the interplay of continuity and transformation ‘in action’, i.e. on how change is actually made through people’s actions in transaction with the environment (De Roeck & Van Poeck 2023). Drawing on empirical examples from case studies of diverse settings aimed at creating more sustainable agri-food, mobility, and energy practices, we illustrate how a transactional perspective on transformativity allows to investigate the entanglement of individual and collective learning, to approach learning as a more-than-cognitive endeavour which involves affect, desire, commitment, and imagination, and to gain insight into how facilitators can grasp the transformative educative potential of ‘educative moments’ (Garrison et al. 2015).

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