The purpose of this study was to understand the obstacles faced as well as strategies used by 6 graduates of a small rural high school in Southern Middle Tennessee. Specifically, this study was an examination of the life experiences of 6 graduates, identifying the major obstacles faced and the successful strategies used to complete the requirements for a high school diploma. Qualitative methodology guided this study. This approach allowed for the lived experiences to be examined and the voices of 6 participants be heard. Data collected included participant stories using semistructured interviews conducted using an interview protocol, drawing of a concept map, and prioritization of influences according to their perspective regarding their diploma completion. Other valuable data included researcher field notes and graduation coach file notes. Findings are presented in 6 themes pertaining directly to the interview questions regarding key elements—circumstances leading to a relationship with a graduation coach, discussions during grad coach sessions, nongrad parent influences, parent expectations, grade retention, and strategies implemented by the graduation coach. After the collection and analysis of all data, the researcher coded the data to determine emerging themes. Much of the researcher’s work consisted of processing the data to discover categories and patterns among the stories told by the 6 graduate participants, as presented in the qualitative narrative analysis methodology. Through the narrative inquiry method of this study, the examination of the stories of 6 graduates reveals that a relationship with at least 1 caring adult in the high school setting is imperative to successful high school completion. This adult may offer assistance through a variety of ways such as developing an academic plan of action, building confidence, arranging tutoring sessions, or tracking progress.