Regenerative agriculture, an alternative form of food and fiber production, concerns itself with enhancing and restoring resilient systems supported by functional ecosystem processes and healthy, organic soils capable of producing a full suite of ecosystem services, among them soil carbon sequestration and improved soil water retention. As such, climate change mitigation and adaptation are incidental to a larger enterprise that employs a systems approach to managing landscapes and communities. The transformative potential of regenerative agriculture has seen growing attention in the popular press, but few empirical studies have explored the processes by which farmers enter into, navigate, and, importantly, sustain the required paradigm shift in their approach to managing their properties, farm businesses, and personal lives. We draw on theories and insights associated with relational thinking to analyze the experiences of farmers in Australia who have undertaken and sustained transitions from conventional to regenerative agriculture. We present a conceptual framework of "zones of friction and traction" occurring in personal, practical, and political spheres of transformation that both challenge and facilitate the transition process. Our findings illustrate the ways in which deeply held values and emotions influence and interact with mental models, worldviews, and cultural norms as a result of regular monitoring; and how behavioral change is sustained through the establishment of self-amplifying positive feedbacks involving biophilic emotions, a sense of well-being, and an ever-expanding worldview. We conclude that transitioning to regenerative agriculture involves more than a suite of 'climate-smart' mitigation and adaptation practices supported by technical innovation, policy, education, and outreach. Rather, it involves subjective, nonmaterial factors associated with culture, values, ethics, identity, and emotion that operate at individual, household, and community scales and interact with regional, national and global processes. Findings have implications for strategies aimed at facilitating a large-scale transition to climate-smart regenerative agriculture.