A qualitative investigation utilizing a phenomenology approach via one-on-one interviews with 35 veterans was conducted to explore the challenges Australian military veterans have experienced in civilian employment settings. Thematic analysis developed four major themes: starting over, mental health, interpersonal cultural difficulties, and organizational differences. Initiatives aimed at addressing unemployment and underemployment for veterans should focus on preparedness, education, and expectation management for both veterans and civilian employers/colleagues and focus on interpersonal and organizational cultural differences, including structure, teamwork, role clarity and feedback, an understanding of military skills, and reduction of mental health stigma and discriminatory practices.