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Everyone who serves in the military (and survives the experience) will eventually become a Veteran, and most will face the challenge of finding a civilian job. This paper investigates how contemporary Veterans experience the transition period between military exit and entrance into civilian life and how their own actions before separation shape their post-transition outcomes. We follow 35 servicemembers through the transition process, interviewing them before and several months after they left the military. These interviews reveal the importance of three factors – the conditions triggering their exit, the strength of their military identity, and their own planning (or lack thereof) for the transition to civilian life – in enhancing or detracting from achievement of a stated post-military goals and objective success in moving into work or school. The strength and depth of an individual’s institutional identity shapes how and when servicemembers plan for military exit and how they adjust to unanticipated military exits. Early planning reflects anticipatory socialization for new civilian roles and is associated with better post-military outcomes. But early planning is often hindered by a strong military identity or facilitated by a weak military identity. These findings have important implications for the military and advocates who serve them with the recent military policy changes to transition assistance and the retirement pension system that encourage early planning for post-military life.