Emerging evidence highlights employment as a key factor influencing the success of transition from military to civilian life. Historically, employment programs have focused on improving skills such as resume writing and interview skills. However, it is likely that employment challenges are more than these practical barriers. Four focus groups with employed and unemployed Gulf War Era II veterans were conducted aimed at moving past a practical perspective by gaining experiential understandings of veterans’ employment. Thematic analysis indicated that the veterans’ employment experiences were best understood temporally in two master themes: pretransition and the divergent experiences of veterans who did and did not plan ahead and living the transition and the veterans’ experiences of employment barriers and facilitators. Further to the two master themes, an underlying thread of the need for self-determination was evident. Interpretation of the results led to the development of recommendations for policy, service provision, and future research.