Increases in the number of enlisted veterans transitioning from active duty to the civilian world have drawn attention to a need for research in terms of unemployment to examine how separated service members experience transition from their perspective. Fifteen separated enlisted veterans from four of the five military branches were selected and interviewed in this study. The focus was to understand better the complexities of reintegrating into the civilian workforce, as experienced by veterans from the enlisted military population. By using qualitative methodologies including exploratory interviews and a focus group, the findings revealed four major themes on how service members described their transition experience: (a) perception that military leadership does not provide adequate support when transitioning and the need to become more self-directed in one's own learning; (b) belief that the military TAP class is helpful but needs major changes to truly be effective; (c) description of a battle buddy or a family member as a positive influence in helping with the transition process; and (d) experiencing significant challenges with civilian employers when transitioning out of the military. An analysis of the findings led the researcher to conclude that transitioning veterans must become self-directed in their learning in order to transition successfully. Moreover, because they are at varying levels of being self-directed when they transition, additional guidance is needed from military leadership, family, and other veterans for the purpose of their development. The analysis also yielded a principal recommendation for military leadership to advocate for quality training programs that are specified from the separated enlisted population for what resources they need to assist with transition to the civilian sector. Additional recommendations were presented to transitioning service members on the importance of managing their own success and believing in their abilities to be resilient, valuable members of the civilian community. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]