The growing visibility of the transgender population acts on and challenges the social-structural constraints of the gender binary. In a culture that subscribes to a gender binary, transgender bodies and transgender expressions exist outside the boundaries created by the binary. Discrimination, harassment, and violence are used to ensure the maintenance of the gender boundaries. The transgender experience often shines a light on these boundaries and the conflict around them. The primary objective of the project is to show the complexity of gender through the experiences of the transgender individual. The project consists of monthly columns published in two newspapers, blog posts and a video series. The project combines a heuristic inquiry of the author’s own experience as a trans man with a meta-analysis of degendering and transgender literature for the methodology.