Even though, living labs have always referred to alternative futures, this chapter explores how capacity for future thinking can be enhanced in living lab practices. The aim is to advance current smart city visions through establishing bottom-up participatory innovation paradigms. We introduce Citylab Rotterdam, as a platform for participation and co-creation, where students, researchers, and teachers, co-create with local entrepreneurs, civil agents, and citizens, to rethink the future of Rotterdam. In this way, we take stock of the accompanying living labbing approach, which is rooted in the local social infrastructure of Rotterdam. Through deliberate training, insight-giving, and anticipation capabilities, we aimed participants to become more sensitive to identifying weak signals for significant change. And consequently become smarter citizens with future thinking capability, empowered to contribute to the smart city debate.