Inspired by “Filipino National Artist for Literature” Nick Joaquin’s novel The Woman Who Had Two Navels (1961), the Philippine pavilion confronts the tension between the vicissitudes of the past and the challenges of constructing contemporary subjectivity. It highlights two ‘navels’ that are in constant dialogue: the forces of colonialism and neoliberalism. The juncture of these two ‘navels’ represents an emergent wave of postcolonial anxieties born out of the process of exiting the colonial condition. To address this emerging post colonial anxiety, a think-tank was created, composed of future architects, planners and designers from selected Philippine schools and organisations to respond to the two ‘navels’ in the exhibition through the lens of three Philippine metropolitan cities. Through the speculations about the intertwined forces and the concomitant architectural and urban issues, Philippine freespace anticipates possibilities for renewed life and hope.