This article addresses the question why initiatives in the field of green business and sustainable development often fail. Therefore, it dismantles some typical patterns of failure and shows – as a case study – how these patterns can be challenged through an innovative educational concept: the green business and sustainable development school. The applied methodology is a real-life project that is designed through blended, interdisciplinary elements from business model canvas, Theory U, participation and design thinking. The results of the school initiative are discussed and evaluated by four distinctive stakeholder groups and outline the school’s supporting potential to overcome typical patterns of failure by the younger generation in the future. This article concludes with ideas to enhance the school concept reaching out to even more stakeholder-groups to increase its reliability and viability.