This paper explores how white fragility and performances of allyship shape efforts to engage Indigenous wisdom within transition-oriented design practice. Drawing on reflexive accounts of encounters with Māori knowledge holders in Aotearoa New Zealand, it examines the affective, relational, and ethical dimensions of engaging across different knowledge systems. While transition design increasingly recognises the importance of worldview change and relational approaches to sustainability, less attention has been given to how privilege, entitlement, and desires for moral legitimacy can constrain such work. Through moments of discomfort, contradiction, vulnerability, and relational opening, the paper argues that meaningful engagement with Indigenous wisdom requires more than inclusion or good intentions. Instead, it calls for humility, patience, accountability, and an acceptance of uncertainty and partial understanding. From this perspective, transition design emerges not simply as a framework for systems change, but as an ongoing ethical practice of unlearning, relational accountability, and becoming otherwise.