According to Schon (1987), design is a form of artistry and making, where learning about a specific topic or design emerges through actions (conscious and unconscious) and heuristics. The designer learns how to design by knowing and 'reflecting in action', reinterpreting and re-elaborating actions in the particular moment where the act of design takes place (Schon, 1987). This allows the emergence of not only new meanings and coherences, but also reason and knowledge about the creative act. This article presents the optimistic perspective of early CAD proponents in the early 60s that, supported by cybernetic and Artificial Intelligence theories, had as main goal the development of 'creative enhancers'. This vision is contrasted to the contemporary digital design scenario, discussing the relevance, pertinence and current use of the digital towards the material. Finally, it reveals key aspects of the myriad translations between the imagined, the perceived and the executed, identifying problems and new alternatives for the creative use of what today is ubiquitous and generic in terms of skills available for architects.