If sustainability is to be an integral part of rethinking education organization, it is necessary to redesign mental models that shape present curricular structures. Assumptions underlying the design of most schools and curricula are based on linear industrial models, which raises an essential question: How can we use opposite concepts of systems dynamics and living structures to create a shift in our present thinking about curriculum and learning for sustainability? From this, we can begin a dramatic design shift toward innovative curriculum to prepare future students and teachers. This article begins with a critique of modern industrial education, then moves into an overview of sustainability concepts and structure through systems thinking. The article then presents the research of an original sustainability curriculum that structures assessment to measure systems thinking. From the results, the article then explores a conceptual design framework for a 21st century curriculum that bio-mimics living systems and organic molecular structure, based on systems thinking and mechanistic principles. By placing assessment on competency relationships and not solely assignment completion, this new framework encourages students and educators to develop emerging 21st century skills in the age of digital technology and communication. This essay and framework, which emerged from the author’s dissertation research and findings, offers a new conceptual tool to the field of sustainability education while challenging educators to adopt living systems into their own instructional designs.