In this article, the author draws on contemporary science to illuminate the relationship between early play experiences, processes of self-development, and the later emergence of the fractal self. She argues that orientation within social space is a primary function of early play and developmentally a two-step process. With other people and with objects in the environment, children first move from the inside out, using feedback provided through early play to calibrate internal systems. Once children coordinate sensory, affective, cognitive, imagistic, and behavioral systems, they then switch modes to navigate from the outside in, via conceptual maps provided by external social and informational cues. If they achieve full social orientation, their imaginations remain for them portals to reality throughout their lives. Otherwise, they mobilize inner resources in defense of a lost, disoriented, or fragile self. A fractal model suggests that the whole of the self, intact during early play, exhibits self-similar resonances in the content and forms of self-expression throughout life.