The paper argues that Bibikhin sought to bridge the contradiction between continental and analytical philosophy by construing Heidegger and Wittgenstein in the tradition of hesychasm. A key to this synthesis is first proposed: the doctrine of thoughts, which enabled him to conceive of ascetics as the art of improvisation. It is found that Bibikhin transformed Bakhtin’s thesis of safe and dangerous children, making it a reference point when talking about the continuity of the Eastern Christian ascetic tradition. The institutional foundations of Bibikhin’s occupation with Hesychast theology are exposed, and it is demonstrated how Bibikhin differs from those intellectuals who have reinvented the intermittent religious tradition as supposedly contiguous. It is shown that the technological origins of the Renaissance are directly correlated by Bibikhin with the technique of fighting thoughts. Thus the parallels between ascetics and art become productive, and dialectics is rejected for the sake of finding moments of salvation in the Christian sense equally in the works of Heidegger and Wittgenstein. A detailed analysis of one of the episodes of Bibikhin’s diary entries shows how this thinker formed a model of the self-development of philosophy, similar to the autonomous action of prayer in Hesychast ascetic practice.