This chapter sheds light on the multiple aspects related to the experience of making art and is a close observation of literary creativity as an artistic activity. To pursue a deeper comprehension of the complexity of relations between artistic activity and psychological, social and cultural aspects, I apply the dialogical perspective and provide a semiotic cultural psychological account on making art. Drawing from the theoretical framework, I conceptualize art-related experiences, as well as the process of making art, in terms of the meaning-making processes that unfold in interactions with sociocultural surroundings. The findings from the single case study revealed the conservative tendencies, involvement of the pleromatic side of identity (Pleromatic side of identity cannot be verbally specified; however, it sets up an inclination to respond in a way that is filled with affective determination (Kullasepp, On becoming a psychologist: Emerging identity in education. Routledge, 2022). It proves the primacy of affective relating with the environment over its cognitive counterpart) and Others in regulation of the processes of artistic expression. Contemplations of the past shed light on the writer’s embodied experience during creation and transitional dynamics manifesting in changes in affective–psychological functioning.