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Sustainability features in the national and local policies of many countries, but there is often a lack of clarity about what it means in practice. Interpretations of sustainable development (or sustainable cities and places) vary widely between different countries and social, economic, political, and environmental actors and interest groups influenced by underlying values and specific contexts. Considering the already-felt impacts of rapid climate change and ecological breakdown, continuing with business as usual will add more pollution, resource depletion, and lead to economic and societal turmoil under a massive shift or collapse in ecological and climate systems. A significant factor in past and current policy failures is that “weak” rather than “strong” sustainability models have been adopted laced with a voter-enticing rhetoric yet delaying painful (to the current status quo), but essential, changes in production and consumption and a shift in focus away from profit toward human and ecological well-being. This requires clear and ambitious legal, regulatory, and policy frameworks, yet also flexible approaches and “agency” of citizens, employees, employers, and politicians for transformation across different geographical and institutional levels, moving away from competition and greed, making room for experimentation and creativity and old and new forms of collaboration and sharing. Relevant concepts, principles, examples and critiques can be gleaned from the ecological economic, social–ecological transformation, and planning literature, offering direction for the kinds of shifts in placemaking to achieve social and environmental justice and well-being.