With growing complexity in society, designers are entering the fields of organizational studies and social change with high levels of responsibility and, sometimes, little background knowledge of theories and recent evolution. Specifically in the fields of strategy, change, and transformation, the turn toward complexity science is gaining acceptance in both academia and practice. This article presents Imagineering as a complexity-inspired design approach to effectuate transformational objectives. It illustrates the method with an application on the city of Antwerp. The author concludes by reflecting on the implications and perspectives of the method for transformational design and for design thinking in management.