Armed forces are reinventive institutions that shape the identity of their members. Leaving the military involves an adjustment to civilian employment that may be turbulent at times. The aim is to understand the experiences of self and other military healthcare professionals' midlife career transitions. This qualitative study applied heuristic inquiry research methods. This included a thematic analysis of the researcher's personal experience (diary and reflections) combined with data from interviews or communication with other veterans (n = 10) within a creative synthesis. The themes identified within the study were: The tipping point for leaving; adjustment as a veteran; progression within a new workplace. We experienced a divergence in values away from military service leading to a tipping point for leaving that was followed by a triple whammy of uncertainty about leaving, insecurity in a new job, and loss of identity that impacted mental wellbeing and needed to be overcome. This study has revealed new insights about being a military veteran and transitioning to civilian employment. These insights could lead to changes in how veterans prepare for a midlife career change, retention of personnel within military forces, and how civilian employers support veterans.