The philosopher Lev Shestov aimed to establish a new free way of thinking, which manifested itself as a struggle against the delusion that we have a rational grasp of the necessary truths on matters that are of the greatest importance to us, such as the questions of life and death. Philosophy, as the Russian philosopher understood it, is not pure thinking, but ‘some kind of inner doing, inner regeneration, or second birth’ (Shestov in Lektsii po Istorii Grecheskoi Filosofii [Lectures on the history of Greek philosophy], YMCA-PRESS, Moscow, 2001, p. 53). Having adopted the notion of the ‘regeneration of one’s convictions’ from Dostoevsky’s vocabulary in his earlier works, Shestov developed the idea of ‘awakening’ further in his mature thought, in which the motif of ‘awakening’ comprised one of the main ideas of his philosophy: the fight for the individual’s right to freedom and to creative transformation at a time when she is in despair or on the brink of death. In this article, I analyse Shestov’s idea of ‘awakening’ as one of the key tropes and developmental characteristics of his philosophical vision. In particular, I argue that, having stemmed from Shestov’s earlier interpretations of Dostoevsky, Shakespeare and Plotinus, in his later writings, the notion of ‘awakening’—the possibility of a fundamental, inner transformation of one’s worldview (probuzhdenie, pererozhdenie)—marked the beginning of a new salvific mode in his writing.