Why are European food systems stuck in a pattern of producing large quantities of food while greatly contributing to today’s environmental and social problems? And what can farmers, businesses, and governments do to get these systems “unstuck” and onto a more sustainable path? These questions lie at the heart of this thesis, which analyzes the potential transformation of the Dutch agricultural sector. The Netherlands is emblematic of Northwestern Europe’s farming sectors: the country produces large volumes of agricultural commodities, but per hectare of farmland it has the highest environmental pressure in the EU. By analyzing the context in which farmers work and transform their operations towards sustainability, we identify knowledge-related, sociocultural, economic, and regulatory types of lock-in that prevent a system-wide transformation. To overcome these types of lock-in, society must turn away from the persistent underlying paradigm of growth, resource extraction, and control over nature. The seeds of such a reorientation can be seen in the bottom-up transformations of individual farmers and regional initiatives. At the farm level, personal characteristics like risk appetite, open-mindedness, reflective ability, and sociability with peers are instrumental in overcoming structural barriers. At the regional level, we observed some signs of bottom-up reorientation through the facilitated redesign of a farm in collaboration with the farm’s stakeholders. On the national level, a clear and unambiguous vision, structural policies to level the playing field for farmers, and transition funds are needed to support the transformation.