The article discusses the origins of Sergei Yesenin’s acquaintance with the novel What Is to Be Done? by N. G. Chernyshevsky: this happened in Spas-Klepikovskaya second-class teacher’s school in 1909-1912. The work was read among the intellectuals, and students outside of school hours argued about it and embraced the ideals of the “new people”. Later Yesenin encountered Chernyshevsky’s novel at the lectures on Russian literature by P. N. Sakulin at Moscow City People’s University named after A. L. Shanyavsky. As a result, a number of elements of Chernyshevsky’s poetics were associatively reflected in Yesenin’s long and short poems as well as in his story Yar. In the works of Yesenin figurative echoes with Chernyshevsky are noticeable. The main ideological moments that worried both writers include: the wonderful future of the Fatherland, the conscious creative arrangement of the earthly paradise in the country. Among artistic means, the writers used the epithet “new”, applied it to the re-interpretation of the biblical laws of human society in terms of freedom, equality and brotherhood. Both writers considered this epithet to be the main element in describing both the process of building a just state system, and in characterizing the creators of a better life. Understanding the importance of the nuances of psychology for each person, Chernyshevsky and Yesenin developed the concept of mystery. Chernyshevsky used the successfully found philosophical solution to create reliable everyday pictures, and Yesenin endowed it with further biblical and mythological meanings, asserting the “mystery” as a comprehensive postulate of sophianism. In his personal life, Yesenin in his youth followed the example of the everyday habits of Rakhmetov, but without repeating the entire line of behavior of Chernyshevsky’s literary character. Yesenin gave his main characters in the story At the White Water (<1915>) unusual names that appear in minor characters and characters mentioned in passing in Chernyshevsky’s novel. However, in order not to assert the comprehensive nature of Yesenin’s borrowings of Chernyshevsky’s creative findings, the article presents other possible sources of names and biographical foundations for some of the poet’s behavioral lines.