This chapter explores a city as a complex adaptive system that encompasses a web of actors and subsystems. It describes a smart city with the intention of illustrating the non-linear nature of projects, the unplanned emergence of events and the adaptive nature of actors. The city of Chiang Mai, Thailand, is used as a case study. For two years, the authors have had direct experience with the smart city initiative as consultants and researchers responsible for drafting Chiang Mai’s smart city plans for 2018–2023. The authors argue that a city should be looked at as being made up of a multiplicity of urban systems – i.e., multi-layers, multi-agents, multi-flows, multi-activities and multi-dimensions. These are fabricated into a complex system. This perspective allows us to have a richer insight into the process of a city’s adaptation to the intervention of smart city policies and for policymakers to have a better grasp of designing smart city projects. Throughout the chapter, the authors provide useful frameworks for practitioners to design smart city projects.