We live in times of rapid changes and unpredictability. Great social challenges of today, such as free access to clean water, food, air, health care and education, no longer come one by one (Agenda 2030). 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 successfully address issues of interlocking problems of unsustainability caused by cultural contingents. Yet, understanding of the ways how culture influences adaptation to sustainable development is still not fully understood, amidst a plethora of literature on systems thinking and complexity science. By resorting to insights from an eclectic pool of knowledge, this presentation seeks more human-centered explanations for the retention of undesired ways of thinking. This is done be exploring the concept of ‘modern outpost of unsustainability’, i.e. a locality exhibiting a complex web of social entanglements that cause and maintain several dilemmas at once. By focusing on the formation of individual mindsets through various cultural carriers of meaning, this study wishes to better understand ways in which particular discourses and social mechanisms may create lock-ins of unsustainability, and what socio-material effects such lock-ins may incur upon institution building, technical development and self-governance.