Current recruitment and retention issues within the armed forces draw links with breach of the psychological contract – the dynamics of the employee–employer relationship. Compared with civilian contexts, a military position is unique, however, there is a dearth of conceptual investigation regarding the lived experiences of military personnel, particularly with respect to how such contracts form. This paper combined a phenomenological approach with the critical decision method to investigate the lived experiences informing contract formation and contract trajectory of ex-military personnel. Lived experiences pointed to the formulation of ‘fuzzy’ contracts, impressions from defence force recruitment, specific tipping points around organisational commitment, and large differences between the fidelity of the idealised and actualised self/job. Seven superordinate themes are elicited that trace the formation and trajectory of the contract. A schematised account of findings is developed to provide avenues to investigate how beliefs form in a military contract context and their outcomes.