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Since 2002 Stellenbosch has offered a multidisciplinary Masters programme in Planning, Management and Practice of Sustainable Development (with a specialisation in development planning), offered mainly for working adult students. One of the challenges of developing a curriculum for this degree is that sustainable development (SD) and ‘development planning’, the focal points of the programme, are potentially very broad concepts, requiring the exploration of a variety of complex challenges in the African context, moving beyond the traditional spatial focus of planning in South Africa. This article explores the various potential meanings of SD, as well as its link with complexity thinking, systems thinking and complex adaptive systems and its implications for planning education and curriculum development. Complex adaptive systems thrive on diversity, creativity, and innovation. The programme is not about spoon-feeding, but about allowing space to explore and discover for oneself the diverse interpretations, tensions and contradictions inherent in planning, development and sustainability. Most concepts (participation, sustainability, planning, development, and so on) have a whole continuum of possible meanings between polar opposites, and it is important to make students aware of the language games people play in order to enable them to move beyond the clichés, myths and spin. Self-managed learning is an important element of this programme and innovative methods have to be found to teach the basics (to kick-start the learning) and create the pre-conditions for lifelong learning, as well as instil the critical, questioning, and imaginative attitude needed to invent the sustainable future we need. In addition to formal lectures and discussion classes, writing skill workshops to teach the important skill of writing, two of the more innovative teaching techniques used to try and bridge the teaching divide are journal writing and group work. In the real world, actor collaboration and group processes are very important methods of building knowledge. Since SD does not have a fixed meaning and is value-laden and multi- (or trans-) disciplinary, it requires democratic and deliberative public processes to give meaning to the concept. For this reason, group work forms an important element of the teaching curriculum and students are required to give feedback on the group process after each exercise and in their journals. The purpose of the journal writing is also to try to stimulate deep, rather than superficial learning and to help make the linkages in support of transdisciplinary learning, where learners are taught to make connections between social, political, economic, biological and physical dimensions and to make use of more holistic ways of thinking. Journal writing and reflections on group work have demonstrated many learning benefits, but also the need for more structure and guidance to steer individual learning processes.