Research carried out following the fall of the Berlin Wall was generally unable to produce a coherent picture of the impact that the German Democratic Republic (GDR) had on “ordinary” people’s lives and identities. In this study, we therefore examine life story accounts from teachers who spent the formative half of their lives in the GDR and the other half in a reunited Germany. We chose this group of professionals as they were representative of an educated class whose task it was to support the state. The focus of the study was the changing relationship between individuals and the political system and society in which they lived. Specifically, we focused on moral evaluations that participants engaged in as a method for exploring their narrative identities. Thematic analyses of 21 semistructured interviews, illustrated here by 3 case examples, revealed how positive and critical dispositions toward the GDR began to form in early adulthood. Critical individuals stressed the gap between the socialist rhetoric of the regime and reality of everyday life and reflected on forms of passive resistance that they engaged in out of personally held moral conviction. In contrast, those who were positively disposed toward the GDR did not exhibit profound political beliefs but described a past life submerged in their immediate world of work and family without feeling compelled to engage in moral justifications for the society in which they lived. The methodology used and the relevance of the findings are considered in relation to liberal capitalist democracies.