Imagination is more important than knowledge, but if intellect does not provide the needed logical structures, capacities for envisioning new possibilities are overly constrained. The sustainability problems we face today cannot be solved with the same kind of thinking that created them, but clarity on what counts as a new kind of thinking is sorely lacking. This article proposes methodical, model-based ways of heeding Bateson's warning about the negative consequences for the ecology of mind that follow from ignoring the contexts of relationships. Informed by S. L. Star's sense of boundary objects, a sequence of increasingly complex logical types distinguishes and interconnects qualitatively different kinds of thinking in ways that liberate imaginative new possibilities for life. The economy of thought instantiated at each level of complexity is only as meaningful, useful, beautiful, ethical, and efficient as the standards informing local adaptive improvisations. Standards mediating the general and specific, global and local, universally transcendent and embodied particulars enable meaningful negotiations, agreements, and communications. Attending to the differences between levels of discourse sets up new possibilities for creative and imaginative entrepreneurial approaches to viable, feasible, and desirable goals for measuring and managing sustainable development.