The theory of transformative learning and its notion of freedom, that we are not trapped by one way of looking at the world or being in the world, fosters a fundamental re-ordering and radical questioning of how one thinks or acts. As a theory of adult learning, it emerged from the women's movement in the US, echoing what it means to become a "transformation learner," realising how societal norms and expectations due to gender roles have defined and limited one's way of being. The purpose of this paper is to provide greater insight into deconstructing gender identity through transformative learning by questioning gender binaries through premise reflection. The paper begins with an overview of (1) Judith Butler's ideas on gender and deconstructing gender as well as (2) Jack Mezirow's notion of transformative learning theory. This sets the stage for (3) bringing Butler's and Mezirow's ideas into conversation, setting the backdrop for a (4) discussion regarding the implications of such a conversation, reflecting on an existing approach from Christine Jarvis.