Contemporary Information Systems management incorporates the need to make explicit the links between semiotics, meaning-making and the digital age. This focus addresses, at its core, pure rationality, that is, the capacity of human interpretation and of human inscription upon reality. Creating the new real, that is the motto. Humans are intrinsically semiotic creatures. Consequently, semiotics is not a choice or an option but something that works like a second skin, establishing limits and permeable linkages between: (i) human thought and human’s infinite world of imagination; and (ii) human action, with its correspondent infinite world of intentionality, of desire and of unexplored possibilities. Two instances are contrasted as two reading lenses of current business reality: IS governance and industry 4.0. These phenomena correspond to the need to take accountability, transparency and responsibility into account, when designing IS and when using such systems through the ecology of connectivity, Big Data and the Internet of Things. Political, social and cultural dimensions are brought into the equation, when addressing the question of the relevance and adequateness of IS theory and practice to respond to contemporary challenges. The message is that what has already been achieved is but a shadow, a pale vision, of what might be achieved in the age of the new Renaissance.