Regional land use planning in the Yukon has a long and unfortunate history of failed efforts. Under Chapter 11 of the Yukon First Nations Umbrella Final Agreement, a new process for planning has been in place since 1993. Through qualitative, interview-based research, I explore possible factors that either hinder or facilitate successful planning. I used the North Yukon regional land use planning effort as a case study example of the first plan to be successfully approved in Yukon history. A number of challenges resulting from poorly defined roles and responsibilities caused notable struggles and conflict throughout the process, but fortunately, strong political support and micro and meso - level organization, combined with a solid team of skilled and dedicated people, allowed the process to ultimately succeed. Lessons learned and recommendations for future regional planning initiatives are discussed.