This chapter elaborates the concept of insurgent planning (IP) and why it needs to be taken seriously in planning education, scholarship, and practice. It describes the crises and social contradictions of the late 20th and early 21st centuries and the implications of the resulting political and ideological shifts for planning. The chapter discusses the political philosophies that drive liberal democratic and insurgent citizenship practices and argues that IP ontologically departs from liberal traditions of so-called inclusive planning that have held the inclusion of disadvantaged groups as an objective of professional intervention. It discusses the potential flexibility of these forms of action and dispels a binary misconception of invited versus invented spaces for citizens' direct action. The chapter focuses on the theoretical construct of IP as practices that are transgressive, counter-hegemonic, and imaginative. It inspires by anticolonial scholars and activists of liberation and discusses the urgency in decolonizing the future as a realm of political contestation and imagination.