After half a lifetime "undercover as a man" I transitioned from male to female while staying involved in the Python community. This talk discusses that transition and explores how I found life in Python as a woman different from my former life as a man. This talk will include a brief discussion of what being transgender means, my experiences as I came to terms with it, and the losses and gains transition entailed. Early on I made the decision to be as open as possible and to stay engaged in the Python community as I transitioned and I will discuss why I made that decision and the levels of acceptance and support I encountered. Transition has been wonderfully successful, but that very transition put me in a surprisingly new world. Now being part of not one, but at least 3 groups that are minorities in the Python world gave me a very different view of a community I thought I knew, and pushed me to being an activist (or trouble maker) in spite of myself. I will discuss the experiences that have convinced me that privilege is very much alive and well in the Python world.