Having lost eight friends in ten years, Cooley retreats to a tiny medieval village in Italy with her husband to recover. There, in this sundrenched paradise, she examines what we all must confront one day, mortality. How do we grieve? How do we go on drinking our morning coffee, loving our life partners, stumbling through a world of such confusing, exquisite beauty? Linking the essays is Cooley’s escalating understanding of another, more painful loss on the way, that of her ailing mother back in the States. Part memoir, part loving goodbye to an unconventional parent, Guesswork transforms a year in a pastoral hill town into a fierce examination of life, love, death, and, ultimately, release.