This article documents the case studies of two Brazilian children aged 10 and 11, for whom drawing is a symbolic tool of self-meaning. Semi-structured interviews were methodologically carried out from drawings they had created previous to and during the interview. Using semiotic cultural psychology as a reference, the concept of Self-imaging is put forward as an alternative to the self-image construct, highlighting the active role of the subject in the construction of his/her life trajectory. Results suggest that the transition process to adolescence represents a challenge in which young people recreate images of themselves by projecting new possibilities of action in the world through their imagination.