In our Western culture, a non-normative gendered life is often seen, even by the individual themselves, as problematic, morally bankrupt or sick (American Psychiatric Association 2000). Terms such as ‘transsexual’ or ‘transgendered’ carry so much stigma (Goffman 1963; Leonard et al. 2012) that most who might be so labelled, go to extraordinary lengths to avoid this labelling and recognition. Their strategies include secrecy, seeking a ghetto, passing to seek misrecognition and seeking a cure. The social pressures to conform to biologically determined binary gendered roles led me to see two ‘lose/lose’ options—either ignore my deepest inner feelings on how I wanted to live and conform to an appropriate gender role, or live as I wanted and be ostracised and stigmatised. By presenting events, experiences and periods in my life, this chapter will demonstrate that I, as subject, both in the sense of being subject to the culture I live in and also because of my self-conscious awareness, was able to gain some understanding of the limits that our culture has over my performance of gender. I will use phenomenological autoethnography to examine my own socially situated subjectivity intersected by non-conformist practices of gender. My subjectivity is examined by exploring the multiple and often contradictory links between myself as subject, my internal agentic voice and the ever-changing society I was living in.