This paper explores the relations between the inevitability of loss and the counter-responses of creativity in psychoanalysis and poetry – particularly in Freud’s short literary essay, “On transience”, written during the First World War, and poems by W. B. Yeats and W. H. Auden. It first notes and details the structural and thematic similarities between the Freud essay and the Yeats poem “Adam’s Curse”, using the close reading methods of literary criticism or Freud’s dream-analysis. Both men achieved their lasting fame and success during the conflict-ridden first half of the twentieth century, and both died in 1939, the year in which the Second World War began. The second part of the paper focuses on three Auden poems of that year, the ominous anticipations of “September 1, 1939” and his elegiac tributes to Yeats and Freud, each of whom was a major influence on his own work and life. What connects all these texts is the issue of how creative endeavours struggle to make and preserve meaning when faced with the twin adversaries of destruction and despair.