Highlighting the ideologically significant factors but paying little attention to the personal beliefs and mindsets are common for publications considering the identity of the Kaliningrad Oblast inhabitants. At best, the authors refer to local myths and stereotypes. To address this shortcoming, we suggest considering the identity as a reflexive construction, strengthened by narratives and controlled by social practices. The paper is aimed to show how the refocusing of thinking of social reality was affecting the Kaliningrad Oblast’s society during the last decade and to reveal its impact on the self-identification of Kaliningrad Oblast inhabitants. The research is based on the interviews carried out by the authors in the summer of 2020. The results of the content analyses of the text materials were compared with the data of previous surveys and research. The analysis reveals that the two opposing cultural phenomena are essential for the regional society: the first is “outdating,” a reflection on the current processes and changes in terms which are relevant for previous periods; and the second is “outscoring,” an introduction of the narratives and practices typical for the post-modern society. The authors hypothesize that the current level of pluralism achieved by the regional society, as well as the combination of the traditional and modern values, provide the necessary resilience for the identity of the Kaliningrad Oblast inhabitants and make it possible to consider this identity as a driver of the regional development. Nevertheless, the current balance is fragile, and it can be threatened by the discrepancy between the politics of identity retention, managed by the traditional state-oriented tools, and the reflexivity of modern individuals, which are weakly regulated by traditions, social prescriptions, or ascriptions. This hypothesis requires further verification.