What happens when we consider transformative experiences from the perspective of gender transitions? In this paper I suggest that at least two insights emerge. First, trans* persons’ experiences of gender transitions show some limitations to L.A. Paul’s (forthcoming) decision theoretic account of transformative decisions. This will involve exploring some of the phenomenology of coming to know that one is trans, and in coming to decide to transition. Second, what epistemological effects are there to undergoing a transformative experience? By connecting some experiences of gender transitions to feminist standpoint epistemology, I argue that radical changes in one’s identity and social location also radically affects one’s access to knowledge in ways not widely appreciated in contemporary epistemology.