This dissertation examines the experiences of women who did not fit the intended life path for educated white women in the early twentieth century, the operation of wealth and power, and the genre of biography, both historical biography and biography written for a non-historian audience. Further, questions related to the construction of the archive—whose documents are saved and whose are discarded—inform this dissertation. Each chapter examines an individual's life in the early twentieth century and follows their trajectory through later life, a less-explored stage. Julia Morgan (1872-1957), Ida O'Keeffe (1889-1961), Alfred Stieglitz (1864-1946), and Mabel Dodge Luhan (1879-1962) form the foundation of this dissertation, while Georgia O'Keeffe's (1887-1986) life and legacy is also explored. Through the methods of women's history, feminist biography, and microhistory, this dissertation utilizes archival research, correspondence, published and unpublished autobiographies, and "canonical" biographies written about historical subjects. This dissertation investigates how individuals have challenged biographers due to a lack of "preferred" sources or how biographers, often ignoring complicating evidence, sought to enshrine a "genius" myth as a part of an individual's legacy. By examining the connections between a woman's public and private life, as well as often overlooked, everyday, quotidian matters, this dissertation offers a model for future investigations into individuals who left sparse records, as well as how to reexamine individuals whose "myth" was created by biographers.