What causes some societies to persist through time while others disintegrate? I will present a conceptual framework—distilled from complex adaptive systems theory, environmental anthropology, historical fiction, and community ecology—that identifies some common elements of sustainable societies. One useful common-sense concept that derives from considering social-ecological systems as complex adaptive systems is the notion that in order to adapt to changes and challenges posed by the environment, feedback cycles between an agent (e.g. an individual in a 'society') and its surroundings must be effective at communicating necessary information to the agent (and, of course, the agent must have both the motivation and capacity to change its behaviour). I focus my energy on understanding how the structure of the system and feedbacks may dictate whether cultural schemata evolve that lead to social and environmental sustainability. Drawing on historical fiction, three case studies narratives about the behaviour of humans in the context of their surrounding environment will be presented to challenge, explore, and refine this framework: 1) a Sanak Island resident from 2012 BC, 2) a Sanak Island researcher from 2004 AD, and 3) a Manhattan resident in 2007 AD.