Pinocchio is one of the most widely read pieces of children’s literature, and has been translated into 200 languages. It has evoked metaphors of childhood’s condition, early description of autism, disruptive behavior, moral development, or even hyperactivity. Less attention has been paid to the aspects of transgenerational relationships, the child’s development trajectory, and their inherent ambivalence, though these are all very relevant in the novel. I use Dialogical Self theory to analyze Pinocchio’s trajectory, tension, ambivalences, and meaning-making. The puppet/boy metaphor displays positive and negative aspects of development that should be critically considered in developmental and educational psychology and should be taken as complementary in educational practices.