This study examined US enlisted veterans’ personal agency during their transition from the military to civilian workforce. Veterans currently working in a civilian corporate environment were involved: 41 were surveyed, 10 were interviewed, and 80 supplied comments to the researcher’s LinkedIn request for responses. Participants were asked to describe their sense of personal agency and how it evolved over the time period before, during, and after military service. Participants offered slightly varying descriptions of their transition experience. In general, participants experienced low agency before military service, minimal agency at the start of military service that grew over time, and an unprecedented and sometimes paralyzing degree of freedom and agency after military service. Transitioning veterans are thus advised to understand that the psychological transition process is complex, increase their competencies through cultural immersion experiences and field research, maintain a learning mindset, and build a relevant and committed support team.