The present paper begins with tracing back to the birth of an information society, better known as the knowledge society. We shall explore the dynamics of this society and its wider implications for post-modern society. The questions that we seek to answer are: What is an information society? How did the various thinkers conceptualise this society altogether? And what is the impact and the challenges that the new society poses for us? As we delve further into the nitty–gritty of the information society, we shall be squatting on the soft terrain of the post-industrial society and try to explain its vicissitudes as if with a magical hoop. What sounds even more interesting is that every time we turn our magical box upside down to show how hard we are for new emergent theories, we are suddenly encountered with a new jet of meanings concerning the digital age and its undercurrents. We never run short of meanings evolving constantly to explain the tide of change in fits and starts. Probably, one strong reason why this paper was written was to appraise us not only of the recent developments in the domain of the information age but also to understand the volatility and malleability that life suddenly poses for us. I shall be explaining the various dimensions of the information society and the risks contained at its various stages. My aim in this paper is not to deter the pace of digitisation but to understand the hazards it entails itself. It shall be difficult to contain the momentum of digitisation, but of course, knowing its perils may help us combat its menace and pitfalls.