Once associated with lifetime employment, policing and teaching have become increasingly associated with employee attrition. We used a life course research design to explore career turning points and transitions, in the context of preceding and following careers. Former police officers (n = 9) and former teachers (n = 15) from around Australia participated in 30- to 60-min interviews about their careers and career decision making. Transcribed interview responses were analyzed using contextualizing and categorizing methods. Although participants’ experiences of ruptures preceding voluntary career change differed, the theme of feeling undervalued as a result of ruptures was common among participants. Participants felt valued in subsequent careers when prior skills were recognized and opportunities existed to acquire and apply new skills. Practical implications include the need for organizations to offer supportive workplace environments that value individual members and their contributions.