In the context of accelerating climate change and global system disruptions, the future is increasingly seen as uncertain, complex, and unpredictable. This chapter explores how this deepening uncertainty is reshaping governance, particularly through the rise of anticipatory governance—a mode of decision-making that acts in the present to prepare for unknown and emergent futures. While climate scenarios and risk models attempt to guide future-oriented policies, traditional forecasting methods are no longer sufficient in a world marked by unpredictability and non-linearity. This shift has profound implications for sustainable development, a concept originally framed by the 1987 Brundtland Report as inherently future-focused. Yet, despite Brundtland’s call to “face up to the future,” mainstream approaches to sustainable development—such as the UN’s 2030 Agenda—still portray it as a linear, step-by-step path with defined goals and endpoints. This creates a contradiction: sustainable development is treated as a predictable journey even as we acknowledge the future is anything but. The chapter critically examines this contradiction, questioning why predictability and linearity remain dominant in development thinking despite growing recognition of uncertainty. It argues that holding onto a fixed roadmap limits our capacity to respond meaningfully to dynamic and emergent challenges. The chapter then explores alternative ways of thinking that embrace uncertainty—not as a barrier to progress, but as a reality to be navigated. Ultimately, it calls for a reimagining of sustainable development as a flexible, adaptive, and plural process. It invites readers to engage in “futures thinking”—to anticipate diverse and contradictory pathways towards sustainability, rather than adhering to one rigid trajectory. In doing so, the chapter encourages a more resilient and responsive approach to development that aligns with the unpredictability of our shared future.