Abstract: It will be argued that urban spaces offer unique opportunities for manifesting in practice future-oriented thinking that is used to shape actions in the present. Urban spaces - and larger or fast-growing cities in the global South in particular - tend to get shaped by constant reinventions of the evolutionary potential of the present as expressed in a wide variety of imaginaries: policy, strategy, and planning documents as well as artistic, fictional, aesthetic, and visual media that respond to the modalities of urban governance, market dynamics, cultural shifts, and socio-demographic changes as individuals, households and businesses make locational choices. However, this uniqueness is inadequately capture by two dominant ways of conceptualizing this dynamic that tend never to meet, namely futuring and experimentation. By futuring we mean the wide range of practices that have emerged over recent decades to explore the future, including forecasting, foresight,and more recently ‘anticipatory thinking’. By experimentation we refer to a wide range of initiatives that demonstrate in one way or another how local actors are responding to the social and environmental challenges. This takes two distinct forms in developed and developing country cities where there is a high degree of informalisation. This paper will propose that in a majority urban world where so much about the future will be determined by what happens within urban spaces (especially major cities in the global South), it will be necessary to synthesize futuring and experimentation to gain a better understanding of anticipatory thinking in an urban context.