Education can transform our cognitive world. Recent use of enactivist and enactivist-friendly work to propose understanding transformational learning in terms of affective reframing is a promising first step to understanding how we can have or inculcate transformational learning in different ways without relying on meta-cognition. Building on this work, I argue that to fully capture the kind of perspectival changes that occur in transformational learning we need to further distinguish between ways of reorienting one’s perspective, and I specify why different ways are differently valuable. I propose that recent approaches to Confucian ritual provide a clue to what is missing in characterisations of perspective transformation and the resultant transformed perspective. I argue that focussing on ritualised interpersonal interactions (as-iffing-the-other) provides a further clue as to what’s missing from a mere appeal to the ritual-based inculcation of new perspectives, namely the kind of lightness and flexibility that some ritualised interactions encourage participants to have, and the deepening of perspective associated with that lightness. I argue that a case study of a project implementing a highly ritualised philosophical practice with prisoners in Scotland shows how these constraints, seemingly paradoxically, function so as to actually deepen the perspectival spaces of those agents. This case study provides a proof of concept for the proposal that certain forms of ritual engagement can reliably bring about the kind of transformation of perspective that is the target phenomenon of transformative learning theory.