The study of coupled human-natural systems has been among the increased focus of scientific investigation for the last decade. Whilst many of the theoretical foundations in the study of complexity in such systems exist for a while, our empirical evidence-based inference reveals more insights into the challenges and opportunities for deeper understanding of the complexity in the coupled systemic interactions. Going beyond simple inferences, such understanding leads us to explore collective pathways of complex group decision-making and the navigation across multi-dynamic and multi-scale landscapes of interactions integrating ecosystem-based considerations to social, cultural and economic social emergence. The presentation will focus on how strengthening collective knowledge flows and interactions related to knowledge acquisition, representation and diffusion provides insight into self-organization, enhancing adaptive capacity, and promotes sustainability and resiliency in such coupled systems. It would also argue that unlike traditional ecological resilience theory, social and thus coupled-systems resilience presents a certain degree of ergodic systemic properties, and has a fundamental probabilistic rather than deterministic character in its spatial and temporal transitions and transformations.