Two prominent 15th century Tibetan nuns, Chokyi Dronma and Orgyan Chokyi, transcended the conventional gender stereotypes of their times to rise to spiritual prominence in Buddhism. Their rejection of the traditional limitations placed upon women resonates with the values of modern Western feminism and merits present-day examination. We will primarily focus on Chokyi Dronma, the pioneer, but will also examine the life of Orgyan Chokyi. The former was born to a royalty, and a life of comfort and wealth, while the latter was born in poverty. Both were forced to endure harsh treatment and abuse. The value to modern women is the notion that whether rich or poor, advantaged or disadvantaged, all women have to overcome obstacles inherent in societal norms. Each of these women achieved enlightenment by refusing to accept traditional female gender roles. Following her ordination, Dronma transformed a small Tibetan village into an economic stronghold, which required her to actively resist being treated as a dependent female. Her relentless efforts to obliterate negative gender stereotypes and sexist logic earned her the superlatives for which she is remembered. She transformed a community that was ill-prepared for an entirely new kind of exemplar of female leadership.