How do Australian planners take action in difficult planning contexts? This chapter uses oral histories with experienced planning practitioners working in the contentious Great Barrier Reef context to reflect on the art and practice of planning. Experienced planners use discerning practical judgments to address conflict, negotiate agreements, and improve plan and policy efficacy. This is despite diverse political conflict and other barriers that hamper their efforts. By identifying and reflecting on the strategies planners employ to take action we highlight the diversity of challenges planners face when delivering outcomes.