Australia’s geographical location (within ‘Asia’)—seen as a negative into the twenty-first century when the nation defined itself as culturally and aspirationally linked to the major Euro-American metropolitan cultural centres (the ‘West’)—must now be reevaluated. After two hundred years of white settlement and of turning its back on the region in which it is located, some Australian writers are writing texts that illuminate an aspect of Australian literature that is in transition, becoming, by definition, in, of, and with the region as well as in, of, and with present time. Art historian Terry Smith’s theory of the three currents of contemporary art, particularly the third current, suggests a new paradigm, a potential break from modernism, and a different kind of entanglement and interconnection in a world that is witnessing shifts in world power, voluntary and involuntary mass movements of people, and real time global communication technologies. Adrian Snodgrass and David Coyne’s application of hermeneutical theory to the architectural design studio via the metaphor of excursion and return illuminates some imaginative intersections, understandings and energies in three texts by Australian authors—Michelle De Kretser, Chi Vu and Jennifer Mackenzie. In Smith’s terms too, the texts perform original leaps of the imagination in their diversity, freshness, and ability to surprise and invite questions about literature’s potential to stir up prior understandings and invite new ways of being in the present. In terms of Giorgio Agamben’s definition of the contemporary, the three texts bring the reader to a plurality and intercultural connectedness that we have yet to fully recognise and live. They represent a line of flight towards a literary imaginary in Australian writing that is contemporary, locally grounded, but also regionally and globally entangled.