Unlearning is a recurrent theme in Japan. To further understanding of what this entails, we focus on the view of learning laid out by a revered 13th century Zen-inspired playwright. For Zeami, learning involved a movement from the acquisition to unlearning of skills, punctuated by an experience of "mushin," followed by creative reemergence. To deepen understandings of this unlearning model, we turn to draw comparison with recent discussions in the Western literature, focusing on Double-Loop Learning and Learning III, both inspired by Bateson. Learning III, which Bateson utilized several Zen references to explicate, appears to gesture towards the alternative punctuation of learning envisaged by Zeami, although differences remain. We then shift to highlight empirical work on contemporary Japanese schooling, highlighting practices which suggest elements of a Zeami-like worldview continue to live on in Japan's learning culture. Unlearning, when viewed as a living tradition embedded in culture, rather than merely a premodern past or future philosophical possibility, help sets the stage for a transnational, transdisciplinary dialogue on how we learn. We perform our own extended dialogue that led to this piece, a mode of engagement we view as methodological innovation, as we work to unlearn our past parochialisms.