This article explores the influential role of planning on recognition-primed decision-making. Considerable prior thinking occurs and there is a need to trace and account for the cognitive processes that precede and guide decisions in dynamic outdoor environments. Seven expert leaders from four countries were interviewed about memorable decisions made on outdoor journeys with an educational focus on land, sea and ice. Four stages of planning were identified: (1) long-term preparation; (2) formal leadership meetings; (3) day-by-day planning on route and (4) thinking immediately prior to the event. The stages sequentially capture the planning progression, illuminating the cognitive processes at each stage to culminate in option selection. In each decision situation, planned goals and actions were implemented through the creation and re-creation of micro-plans. As windows of opportunity presented themselves, the flexible execution of plans was a key feature. Planning provided the solid bedrock upon which decisions were made.