Great civilizations succeed by making the right decisions—but how are those decisions made? Tackling complex sustainability and resilience challenges often requires moving beyond default choices to decision making. To make better decisions, the psychology of choice matters. This interactive session explores how complexity, scale, loss, and gain influence planning choices. It examines motivation through principles of persuasion and modern psychology. The cost of precision and accuracy will be weighed against risk, value, and effort. The session also explores choices made through Traditional Ecological Knowledge, relational framing, and island perspectives, emphasizing "outcomes rather than accounting." This conversation—not lecture—challenges continental and island planning norms while promoting meaningful discussion between attendees about decision-making frameworks that could contribute to better choices and winwin solutions for resilient communities.