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Meeting human needs while sustaining the planet's life support systems is the fundamental challenge of our time. What role sustenance of biodiversity and contrasting ecosystem services should play in achieving a sustainable future varies along philosophical, cultural, institutional, societal, and governmental divisions. Contrasting biophysical constraints and perspectives on human well-being arise both within and across countries that span the tropics and temperate zone. Direct sustenance of livelihoods from ecosystem services in East Africa contrasts with the complex and diverse relationships with the land in Mexico and the highly monetary-based economy of the United States. Lack of understanding of the contrasting contexts in which decision-making about trade-offs occurs creates impediments to collective global efforts to sustain the Earth's life support systems. While theoretical notions of the goals of sustainability science seek a unified path forward, realities on the ground present challenges. This Special Feature seeks to provide both an analytical framework and a series of case studies to illuminate impediments posed to sustainability by contrasting biophysical constraints and human perspectives on what should be sustained. The contributors aim to clarify the trade-offs posed to human welfare in sustaining biodiversity and ecosystem services and the challenges in managing for a sustainable future in which human well-being is not compromised as compared to today. Our goal is to provide novel insights on how sustainability can be achieved internationally through exploration of constraints, trade-offs, and human values examined at multiple scales, and across geographic regions from a range of cultural perspectives.