This project relied on qualitative research as part of the cultural transformation tract for the Doctor of Transformational Leadership (DTL) degree at Bakke Graduate University in Dallas, Texas. The project incorporated an autoethnographic approach combined with peer-reviewed and narrative research to explore the lived experiences of women who have encountered the glass cliff phenomenon during their careers. The study includes an examination of the author’s journey into transformational leadership as a woman of color who has spent many years finding an ethnic identity. The author indicates that her work experiences and guidance from God led her to the topic. When she saw an article on the glass cliff phenomenon, she was stunned to find that her work experience was not unique and that there was research to support the reality of the glass cliff phenomenon. She wanted to know who else had experienced this phenomenon and her question led to this research. The narrative research portion involved women whose perspectives span five generations living in the Philadelphia, Wilmington, South Jersey metro area. The conclusions drawn from the semi-structured questions used for the project are that women often ignore the warning signs and do not ask enough questions about the organization’s infrastructure before accepting a position. The study recommends that women should seek full disclosure about an organization’s infrastructure related to an offered position, full support from the board, and be prepared to walk away from a situation if their requests are unmet.