We live in times of rapid changes and unpredictability. Great social challenges of today no longer come one by one. What makes them great is their ever-greater entanglement in one other and across multiple levels, including landscapes, regimes and niches. To this background, a major challenge facing many countries today is how to address interlocking problems of unsustainability caused by cultural contingents, as this dimension is not yet fully understood amidst a plethora of literature on systems thinking and complexity science. Drawing on insights from 35 in-depth interviews with residents and specialists, this research seeks more human-cantered explanations for the retention of undesired ways of thinking. This is done through the example of Skopje (North Macedonia), a city embroiled in a host of economic, ecological, and social contradictions. Considering the scale, scope, and character of problems in Skopje, we seek to develop a deeper understanding of the situation to outline priorities for action. By conducting a multilevel analysis, the aim of this study is to investigate the role of personal and cultural narratives upon scenarios of unsustainability. The following research questions form the bulk of this study: (1) What are the residents' views on (un)sustainability and (un)sustainable development in Skopje? (2) What are the residents' assessments of their (im)possibility to influence change? (3) What is the role of culture upon the developments in Skopje? Using Skopje as an example, this presentation elaborates on the concept of 'modern outpost of unsustainability', a locality exhibiting a complex web of social entanglements that cause and maintain several dilemmas at once. By focusing on the formation of individuals through cultural carriers of meaning, this presentation explores ways in which particular discourses and social contracts can create clusters of unsustainability, and what socio-material effects they may incur upon institution building, technical input and self-governance.