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An advanced degree is a step toward career aspirations, access to affordable healthcare, and financial goals. For single mothers, a population most vulnerable for living on the brink of poverty, an advanced degree can be a means toward ending intergenerational poverty. Single mother students face serious barriers to advance their education which impede their ability to pursue and complete their degrees. The purpose of the present study was to explore graduate student single mothers’ experiences attending an online education program. The conceptual frameworks guiding the study are Pintrich’s motivational self-regulated learning model for achievement and Duckworth’s model on the psychology of achievement called grit. The study explored the lived experiences of 10 single mother students who are working on their online graduate degrees at Walden University to describe factors that influence their academic success, with a focus on their academic motivation, academic self-efficacy, and social support. The study also identified barriers to their success and ways they cope to overcome barriers. The study used a phenomenological research design, in-depth interviews, and Moustakas’s transcendental phenomenological model for data analysis. Overall, the findings indicate that single mothers in this study were motivated to complete their graduate degree in order to be better in their roles as mothers, providers, and career professionals. The results from the study will be significant for university administrators, government policymakers, and state social service agencies to develop effective programs and policies that support single mother graduate students studying online.