Drawing on approximately 45 semi-structured interviews with soldiers transitioning out of the Army, Navy and Marine Corps, we investigate how they decide to leave, what they plan to do as civilians, and how they go about preparing for life after military service. This project asks how veterans' own expectations, attitudes, and approaches in finding civilian work or training affects their post-military work outcomes. We hypothesize that veterans are active participants in the job search process, and may think and behave in ways that draw out their search for "good" jobs.  Just as civilians may have little understanding of the military experience, and may have unrealistic images of veterans, soldiers and veterans may have mismatched expectations of the civilian marketplace for their labor.  In this paper, we analyze the first round of interviews with individuals before their separation from the armed forces.