ABSTRACT This comparative analysis of sociopolitical and cultural discourses in the Estonian SSR from 1987–1991 concentrates on the tension between postmodernism as a cultural logic of late socialism and neoliberalism as a then-emergent modern ideology. Postmodernist and neoliberal ideas both emerged from decolonial reactions to Soviet rule, albeit from different aspects of it. Postmodernism reacted to the sense that the stagnation-era Soviet regime was ‘stuck in presentness’ and to the Soviet grand narrative of building communism. Neoliberal aspirations developed in reaction to the way Soviet rule obstructed local economic initiative and local participation in the global market, finding support in Gorbachev’s call for enterprise-level economic autonomy.