Operation Enduring Freedom (OEF) commenced in October 2001 and Operation Iraqi Freedom (OIF) and started in May 2003. To date, more than 1 million military personnel have been deployed to Afghanistan or Iraq, with over 21,000 of those deployed wounded in combat (Clark, Bair, Buckenmaier, Gironda, & Walker, 2007). Of those wounded the number of personnel who leave military service and join civilian employment grows. This qualitative transcendental research study examines this phenomenon from the perspective of those who have traversed the path from military to civilian, all while dealing with mental, emotional, physical and career rehabilitation. The sample consists of 25 veterans of the Operation Iraqi Freedom / Operation Enduring Freedom combat areas who were injured and left the military and attained civilian careers. This exploration includes the expectations the veterans had of joining the civilian workforce and how those expectations and other determiners affected the transition in their estimations. The study reveals the factors influencing the veterans as they accepted that first civilian job, what their mindsets and attitudes were, and the situations they encountered in dealing with civilian employment when they initially left the military. This research is an analysis of their lived experiences, and provides recommendations for future research to military, business and government leadership.