As a small state aspiring to First World economic status, Singapore has adopted both conventional and unconventional strategies to achieving this, thus avoiding being completely constrained by the play of regional political and economic forces. The single overarching motivation behind the enlargement strategy is to serve the international community in exchange for the latter’s succour and other protections. One under-explored aspect of this strategy is the Republic’s intermediary functions for the international community of states in diplomacy, maritime and air transportation, and information flows. In diplomatic terms, Singapore pursues an omnidirectional posture of developing friendly ties, short of rigid alliances, with all states regardless of ideology and resource base. In terms of maritime and air transportation, Singapore inherited and augmented geographical and colonial advantages. In terms of information, the Republic hosts filmmaking post-production facilities for leading Western entertainment companies and offers itself as a base for global news reporting on Asia. Increasingly, the Republic is also hosting testbeds for the digital economy. In sum, this case study offers some lessons for small states attempting to succeed economically and strategically by exploiting globalization.