In this lecture, I sketch the content and contours of a deliberately over-simplified contemporary fairytale which I refer to as the ‘Digital Enchantment’. It is comprised of three core tenets: digital solutionism, the absence of ill-effects doctrine, and the celebration of unfettered innovation as one of the noblest and highest callings of this present age. I will seek to unpack this fairytale to demonstrate its enduring, universal appeal, while highlighting the dangers of falling under its spell due to a continued failure to separate fantasy from reality. I argue that the challenge that we urgently face in navigating sweeping on-going digital transformation is to develop means for drawing on the power of the Enchantment’s appeal in ways that enable us to proceed in a more careful, deliberative and clear-eyed fashion in order to reap the best of human creativity that lies at the heart of innovation in the service of flourishing human communities.