This case report is about a regional land-use planning project in the Netherlands. Initiated by the province of Gelderland and Radboud University (RU), the project aimed to create “Communities of Ownership” (CoO’s), local associations of townspeople who would engage in collaborative vision-building related to sustainable land development. The guiding conceptual model was “The Natural Step” (TNS), a systems-level approach to sustainability. We describe the land-use project and the learning history we constructed to help project managers and facilitators learn from the different perspectives that project actors conveyed. The learning history indicated that the project had limited success. We discuss four factors shaping the project’s results and the lessons learned related to those factors. The first lesson concerns the importance of a shared vision for sustainability among stakeholder groups. The second focuses on the preconditions necessary to work with The Natural Step effectively in certain contexts. Lesson three is about what it takes for a learning history to serve as a catalyst for collective learning and project improvement. Lesson four sheds light on the importance of respecting differences in stakeholders’ levels of sustainability awareness. We speculate that these differences may have shared characteristics with the kind of developmental differences that constructivist stage theorists of human development have articulated. Finally, we discuss the implications of our analysis for the leadership of sustainability initiatives.