This thesis focuses on the experiences of former UK military personnel from all three armed services re-entering the civilian workplace. There is a distinct lack of research in this area with only limited studies carried out which tend to focus on the difficult transitions or the actual mechanics of engaging with the civilian labour market. This thesis provides a unique insight into the experiences of military personnel and their journey out of the military environment and into the civilian environment. This study uses a qualitative methodology based upon an interpretive approach to gain insights into the experiences of former military personnel who left the military for a variety of reasons. The study examined the stories of a main research cohorts of 16 individuals and a second cohort of 10 individuals were engaged to further challenge theoretical saturation. The research subjects were selected using a ‘snowball’ approach and selection filtered using a specific set of criteria. Their military experiences span a range of times since discharge and a range of civilian employment since leaving. Following a review of existing literature encompassing career theory, transition theory, narrative analysis and activity theory, open interviews were conducted with participants simply asked to “tell me your story”. The transcripts of the interviews were then analysed using three analytical frames: activity theory, storytelling and perceptions of the self. The participants mainly identified tensions in their relationships with new communities, mediated by the changed social rules and divisions of labour that they encountered in their transition. Those who identified the lowest levels of tension tended to tell their stories in a heroic mode and demonstrated multiple or mixed senses of the self, whilst those who identified the highest tensions tended to tell their stories in a tragic mode and privileged their military identity above their other identities. The data suggests that some of these experience may be connected to the concept of the unquestioned organisation that was expressed by all the research cohort and the unthinking transfer of agency that occurs on joining and leaving the military.