Abstract: The purpose of this study was to examine how Post-911 veterans exiting the military navigate the complex systems of the military, higher education, and the civilian job market to make a self-identified successful transition to the civilian workforce. The research questions guiding this study include: (a) What do the stories of ex-military men and women seeking to re-enter the civilian job market tell us about the overall experience of navigating complex systems? b) What do these military veterans see as the most essential factors and strategies that have led to what they view as their successful job in the civilian workforce? The theoretical framework that guided this study is a combination of complexity theory, Schlossberg’s transition model of adult development, and transformative learning theory. Qualitative data were collected through a long semi-structured Zoom interview, a shorter second interview where each participant shared a symbol of their military-to-civilian transition, and a self-created mind map as a visual representation of their transition journey. The findings reveal that the transition process is interconnected, and that success depends upon each veteran’s situational context and personal characteristics. These veterans all used the strategies of: (a) planning ahead; (b) making and maintaining a network of connections, both civilian, military, and veterans; (c) leaning on family; (d) maximizing their military benefits, and (e) being open to change. Participants also shared how other veterans can fail to use these key strategies. Implications for theory, future research, and practice within the field of lifelong learning and adult education are discussed.