For over 50 years, scientists and other thought leaders have been trying to call attention to the degradation of the foundation of human civilization through unsustainable behaviour (Carson 1962, Meadows et al. 1972, IGBP. 2004, Millenium Ecosystem Assessment 2005, Stern 2007, Intergovernmental Panel on Climate Change 2007, Rockström et al. 2009). The United Nations’ Decade of Education for Sustainable Development (DESD) has recently put renewed focus on not only what we need to learn and teach in the field of sustainable development, but also how we learn and teach about sustainable development. Pedagogical methods such as lifelong learning, social learning, problem-based learning, dialogue education, and transformational learning in Education for Sustainable Development (ESD) have been put forward. Transformative or transformational learning seems especially relevant to ESD as deep transformational change on a personal level might be one of the key aspects needed to facilitate a larger societal transformation. The chapter presents research on transformational learning and the components necessary for it, and provides a case study of a course that works specifically with transformational learning for sustainability. The Advanced Societal Leadership course is a 10-week course of the 10-month Masters in Strategic Leadership towards Sustainability programme at the Blekinge Institute of Technology. This course aims at providing learners with critical insights into how large-scale societal transformation for sustainability might occur, and explores several topics for social transformation. The chapter discusses the pedagogical design of the course as well as some of the challenges and questions that the staff has experienced over the last 9 years in imbedding transformational learning and personal transformational change in a traditional university setting.