Explanations of turnover from extant management research focus on the what (content) and how (process) of turnover. This study engages a sensemaking framework to explore the why (meaning) for employees of quitting or staying at an employing organization, in order to add a new layer to our understanding of retention and turnover. Analysis of data from in-depth interviews with leavers and stayers, both post hoc and in situ, using grounded theory methods, reveals identity and well-being assessment sensemaking cycles, which occur periodically or when threat to core elements of identity and well-being across life domains is perceived. Core elements of identity and well-being include purpose, trajectory, relatedness, expression, acceptance, and differentiation. Perceived threat to identity and well-being across life domains leads to varying levels of psychophysiological strain, coping with threat and strain, and reassessment, often in escalating cycles resulting in turnover and continuing into new jobs. Lack of threat to, or facilitation of, identity and well-being, and successful coping result in retention. Overall, these findings suggest that from the perspective of the actors "being retained" or "turning over," these phenomena are part of a deeply felt quest for positive, congruent identity and psychological well-being across life domains. Along with other research, these findings suggest that when people consider leaving jobs, it may invoke a liminal identity stage, which makes family and other life domains salient to turnover decisions. Implications for research on retention, turnover, identity, well-being, work-life, and psychophysiological health in organizations, as well as practical implications, are discussed.