The study is aimed at revealing the peculiarities of the functioning of the autonomic nervous system (ANS) when performing tasks of figurative transfer of personal meanings (depicting real and desired states) in individuals with different types of self-esteem. Thirty-six healthy adults (18–44 years old) with no artistic experience participated in the experiment. Participants successively painted their actual and ideal states (10 min each) using watercolor. Heart rate variability (HRV) was recorded. Self-esteem was assessed by the Budassi test, psycho-emotional state - by the Hospital Anxiety and Depression Scale (HADS). The dynamics of HRV during drawing and subsequent rest were analyzed, as well as its relationship with the type of self-esteem (adequate vs. inadequate). The groups demonstrated opposite autonomic responses. During the transition to drawing of the desired state, individuals with adequate self-esteem showed a decrease in the high-frequency component of HRV (HF, parasympathetic activity) and an increase in SDNN (total variability), indicating sympathetic activation. Individuals with inadequate self-esteem showed increased parasympathetic influence (growth of MeanNN, MedianNN). In the resting phase, the adequate group retained sympathetic tone (LF/HF growth), whereas the inadequate group had a pronounced parasympathetic “rollback” (NN-intervals growth). Significant correlations of anxiety/depression with HRV parameters modulated by the type of self-esteem were revealed. Self-esteem is a key modulator of autonomic response to emotionally significant imagery activity. Adequate self-esteem is associated with a mobilization pattern of the ANS that supports cognitive-emotional engagement, whereas inadequate self-esteem is associated with a compensatory parasympathetic response. The results highlight the potential of guided imagery in the context of self-regulation and the need to consider self-esteem in personalized interventions.