<p><i>Perezhivanie</i> as one of the main concepts of Cultural Historical Activity Theory (CHAT), related to psychology and personality development, has been widely used by scholars interested in pedagogy, teacher training and language learning. However, multiple interpretations and vagueness of the concept have made its meaning too elusive. This article a theoretical contribution to further development of this category through enriching it with Bakhtin’s aesthetic theory, informed by autoethnographic material. Bakhtin’s theory of artistic creation can provide analytical tools to understand the creative process of deep changes in the psychological system through an aesthetic lens and conceptualise it via literary devices. In this article I propose three situations (absurd, picaresque, and ressentiment) as examples of how the dialogue between CHAT and Bakhtin’s aesthetic theory can provide insight in understanding deep personality change and development. In the end, I have used the theoretical framework as an interpretive tool to briefly analyse the autoethnographic data in relation to my own situation of becoming an environmental scholar-activist.</p>