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Thrivability is a novel concept describing the intention to go beyond sustainability, allowing a system to flourish (Russell, 2010). For a society or organization to be thrivable, educated, responsible acting agents are needed. Traditional education focuses on (efficient) reproduction of existing organised bodies of information (Dewey, 1938). We argue that complex adaptive systems theory and chaos theory provide concepts well suited to inform the design of learning environments, in order to facilitate a thrivable organization. This learning is not linear and externally controlled, but happens in a chaotic, yet guided manner. After discussing the suitability of the theoretical body of these general approaches, we show how a concrete progressive education approach, called the Dalton-Plan pedagogy (Parkhurst, 1923, 2010), implements and supports these elements. By doing so, we show that the Dalton-Plan pedagogy is well suited for education of agents working in and for thrivable organizations. Support for teachers as part of this evolving learning system is provided by an e-learning environment.