“Technology” is lately equated with hardware and software, but for the Ancient Greeks, a technology combined two linked features: the doing of an art/craft (techne) and theorizing about the doing (technologia). We thus consider a “technology” as a “sociotechnical system” – an entanglement of humans with one another, the tools, arts, crafts, practices and institutionalized forms of life of their time. Writing systems and new media are each relevant to understanding the roles of technologies in development, considered at an ontogenetic or historical level. We consider two ostensibly conflicting claims by Piaget that lead to the question of how the postnatal environment fundamentally differs from the intrauterine environment and how this difference changes the process of development. Vygotsky’s focus on the cultural/historical mediation of social relations helps us understand the dynamic interplay of technology and development as part of a single process of human development – and to resolve Piaget’s multifaceted views. To illustrate the insights offered by our cultural-historical approach, we compare the ancient period coupled with the development of literacy/numeracy and current historical circumstances in which new digital technologies are the focus. These two cases illuminate ways current changes are replaying in new circumstances a developmental process as old as Homo sapiens.