This chapter identifies a variety of human obstacles to achieving sustainability, and in doing so provides a deeper understanding of the challenges of sustainability, and the means by which these challenges might be overcome. Human attributes, practices, norms, settings, structures, cultures, institutions, systems, and policies may all be conducive or not conducive to sustainability, so the obstacles surveyed include structural determinants of the footprint intensity of consumption, cultural and social factors, systemic failures of public knowledge, aspects of human cognition, emotion, and motivation, and limitations of environmental governance. The character of these obstacles to sustainability demonstrates the need for a multi-scale and coordinated public response to problems of sustainability, but also self-organized collective efforts to create conditions favourable to global cooperation. The chapter concludes that agreement on fair principles of cooperation is essential to sustainability.