Alongside increasing attacks on New-age thinking by scientism, astrology itself is frequently enframed in a Cartesian worldview and a post-Enlightenment inversion, rooted in the psychology of the Self. Important philosophical questions that have a direct impact on our practice, especially those raised by Jung concerning the uncanny, continue to be brushed aside. We will reassess Jung’s impact on modern astrology and consider how far divinatory astrology, especially practical horary, is more true to his vision than any pre-supposed ‘map of the psyche’. This will allow us to see how, and in what ways, cosmological symbolism and divination continue to reveal an intelligent cosmos, bridging the subject-object split and recreating for their practitioners a sense of the ‘One World’ of the ancients. In addition, insights from Chinese philosophy suggest there is a mysterious, unfathomable power in divination that brings about transformation for its participants. Using examples, we will explore how divinatory space and the dialogue between client and diviner reveal the moral virtue of humanity, and turn the client towards truth. Illustrated by example charts including natal, horary and ‘things suddenly happening’.