This article examines the evolution of cultural values in Mikhail Bulgakov's writings through the lens of Yuri Lotman's theory of "culture of shame" and "culture of fear." Analyzing Bulgakov's depiction of doctors and writers, the study traces a transition from the pre-revolutionary emphasis on professional ethics (shame) to the Soviet era's pervasive atmosphere of fear. The author argues that Bulgakov's characters, initially embodying a strong sense of professional duty, gradually succumb to disillusionment and fear under the oppressive regime. This shift is reflected in the narrative style and character development across Bulgakov's oeuvre, culminating in The Master and Margarita, where the conflict between the individual's ethical imperative and the power of the state is explored. The article concludes by considering the text as a symptom of broader cultural transformations.