Current discussions on the importance of retirement are largely built on statistical analyses of longitudinal data showing that well-being seldom changes from before to after entering retirement, but is rather mainly dependent on the individual’s social resource position. In contrast, qualitatively oriented researchers underline that the retirement process is a complex life transition that needs to be further illuminated. To do this, however, we need to advance new theoretical and methodological perspectives. In this article, an existential sociology approach is outlined, emphasizing the multifaceted spectra of lived experiences and meaning-making in the retirement process. The phenomenological approaches of existential sociology allow us to consider how the exit from working life is created in the processes of motion rather than as expressions of static positions. A merit of this approach is that retirement as an empirical case may say something general about being in transition as a basic social condition. In the article, we discuss how a socio-biographical methodology, based on longitudinal qualitative interviews, helps us capture how existential meaning is formed and re-formed in the ambiguous situations which arise in similar life-course transitions. Theoretically, we especially draw on concepts from the existential anthropologist Jackson and the phenomenological tradition of existential philosophers such as Arendt and Heidegger.