This dissertation analyzes the life writings of Adzom Drukpa (1842-1924) including a Tibetan language autobiography by Adzom Drukpa and a biography of Adzom Drukpa written by his son Gyurme Dorje (1895-1959). Comparison of these texts demonstrates they paint distinct yet resonant portraits of Adzom Drukpa, one emphasizing his human limitations and the other portraying him as a Buddhist deity. While many scholars argue such hagiographical and idealizing conventions in Tibetan life writing obscure its historical qualities, this dissertation examines instead how Adzom Drukpa's life writings creatively balance the human and divine, even while providing specific details about circumstances in eastern Tibet during the tumultuous nineteenth and twentieth centuries. The texts feature accounts of political violence and Buddhist institution building. This dissertation's analysis centers the life writings' depictions of Adzom Drukpa meeting a mysterious lady who appears in the sky. She gives Adzom Drukpa instructions that reverberate throughout his life, including advising Adzom Drukpa not to be a celibate monk but rather to find a woman consort. This dissertation contextualizes Adzom Drukpa's life writings through analyses based in gender, sexuality, and women's studies. Considering the lives and writings of women who were Adzom Drukpa's associates such as Sakya Jetsunma (1836-1896) and Sera Khandro (1892-1940) permits deeper engagement with how Adzom Drukpa's own life writings depict particular women's lives and how these narratives depict gender and sexuality in the context of Buddhist practice. The dissertation also considers Adzom Drukpa's conversation with the lady of the skies using analyses based in religious studies, considering how the narratives depict other paranormal encounters with non-human beings, including animals, ghosts, and a range of deities and demons. Many scholars argue the prevalence of such extraordinary accounts in Tibetan life writing renders the narratives unrealistic. However I examine how these texts depict such events as grounded both in everyday life and in Buddhist philosophy and practice. Like the texts' dual depictions of Adzom Drukpa's character as human and divine, Adzom Drukpa's conversations with the lady of the skies show how these life writings take a creative, considerate, and critical approach to humanity, divinity, and revelation.