The first part of this paper examines the differences between Piaget’s constructivism, what Papert refers to as“constructionism,” and the socio-constructivist approach as portrayed by Vygotsky. All these views are developmental, and they share the notion that people actively contribute to the construction of their knowledge, by transforming their world. Yet the views also differ, each highlighting on some aspects of how children learn and grow, while leaving other questions unanswered. Attempts at integrating these views [learning through experience, through media, and through others] helps shed light on how people of different ages and venues come to make sense of their experience, and find their place – and voice – in the world. Tools, media, and cutural artifacts are the tangible forms, or mediational means, through which we make sense of our world and negociate meaning with others. In the second part of this paper, I speak to the articulations between make-believe activities and creative symbol-use as a guiding connection to rethink the aims of representations. Simulacrum and simulation, I show, play a key role besides language in helping children ground and mediate their experience in new ways. From computer-based microworlds for constructive learning (Papert’s turtle geometry, TERC’s body-syntonic graphing), to social virtual environments (MUDing). In each case, I discuss the roles of symbolic recreation, and imaginary projection (people’s abilities to build and dwell in their creations) as two powerful heuristic to keep in touch with situations, to bring what’s unknown to mind’s reach, and to explore risky ideas on safe grounds. I draw implications for education.