AbstractAnticipatory thinking (AT) and design have many commonalities. We identify three challenges for all computational AT systems: representation, generation, and evaluation. We discuss how existing artificial intelligence techniques provide some methods for addressing these, but also fall significantly short. Next, we articulate where AT concepts appear in three computational design paradigms: configuration design, design for resilience, and conceptual design. We close by identifying two promising future directions at the intersection of AT and design: modeling other humans and new interfaces to support human decision‐makers.