As recent attacks on the rights of women and gender minorities exemplify, sexism and gender privilege are structural forces ingrained in the fabric of U.S. society. Unfortunately, higher education is not immune to such structural forces and can reinforce the power associated with gender privilege. This phenomenological research study, in concert with my own recollections and anecdotes, critically examines how structures within higher education support the empowerment of privilege through the stigma of unpartnered motherhood and the femininization of caregiving. The study explores the experiences of nine unpartnered student parents who directly encounter significant structural barriers related to sexism and gender privilege. Through narrative-storytelling and poetic analysis, this study documents the lived experiences of nine diverse unpartnered mothers living with extreme precarity, facing incredible uphill struggles to make a new and better life for themselves and their children. The research findings uncover a high level of mental health challenge for unpartnered mothers and their children but also a high level of motivation and desire to succeed within their selected programs. The study also uncovers how capitalist influenced ideals of motherhood conflict with standards of ideal scholarship to create an identity crisis whereby one is forced to choose between being a good scholar or a good mother. Practical recommendations are provided for service providers including administrators, faculty, and student service units. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]