Understanding why military students pursue a master's degree has become more important as the number of military students taking advantage of education benefits through the Post-911 Veterans Educational Assistance Act of 2008 has increased. The purpose of this qualitative case study was to explore how U.S. Army officers attending the Command and General Staff College (CGSC) decided to enroll in a master's degree program. Four research questions guided the study to determine whether and how career requirements, post-military aspirations, family considerations, and previous academic experience influenced the choice to pursue a master's degree. A conceptual framework comprised career development, career decision making, and adult development that provided additional guidance. The study used a case study methodology, and 26 military students participated. Data collection comprised interview and surveys, and data analysis comprised coding with peer review and member checking. The findings affirmed the research questions and identified themes related to self-efficacy, goal setting, persistence, and time management, leading to implications.