Leisure-led regional development refers to leisure as a mechanism to achieve broad societal goals within a region: economic revenue, employment and service levels but also cultural or conservationist ambitions. Engaging in such leisure-led regional development proves a complex matter. Based on ethnographies of leisure in the Dutch province of Fryslân conducted over a five-year period between 2013 and 2018, this paper argues that combining theoretical understanding of complexity theories with analyses based on both evolutionary and discursive approaches results in enhanced understanding of the interactions shaping uncertainty in leisure development. Results of field observations, interviews, participation and document analysis show that planning for leisure-led regional development should consider autonomous and evolutionary processes, whilst focusing on purposefully influencing the interactions and perspectives of actors in leisure. More precisely, this means shaping the narratives and practices in these institutions which make specific interactions more likely to develop. This can be undertaken by including in planning efforts the individual perspectives and emotions among actors in the regional leisure sector. To cope with uncertainty at the heart of leisure-led regional development, an adaptive strategy should be adopted, both in the planning efforts taken and in how such efforts are monitored and evaluated.