“Trying to Wake Up” is the first result of cooperation between man and machine in the history of Russian literature. The man is Pavel Pepperstein, writer, artist, visionary. The machine is NeuroPepperstein, a ruGPT-3 linguistic model trained on a corpus of Pavel's texts and capable of imitating his style to such a degree of verisimilitude that we leave it up to readers to guess who is behind each of the 24 stories in this book. The kaleidoscope of plots in this collection is of interest not only as an experiment at the intersection of literature and technology, but also as magical fairy tales that melt reality - you will find a new reading of "Turnip", chess games that change the course of history, a meeting between the saboteur Rebrov and the powerful Ancients, a mysterious the squirrel of oblivion, as well as ghosts, dreamers and sorcerers. Can Pepperstein's psychedelic realism reach new, heady, and titillating heights with the help of a digital imprint of his talent? What makes an author a writer and can neural networks claim this title? What does the future of literature look like and where do human criteria for evaluating it end? “Trying to Wake Up” suggests answers to these questions and asks new ones.