The article seeks to delineate the often misunderstood idea of speculation that has conceptually been converted from an epitome of pure thought into an economic category of profitability and self-interest. But to define speculation already means to pose a problem. In Augustine speculation designates the mutual relationship between reflection and the mirrored appearance of God’s gaze. This dictates an unattainable task of catching God’s gaze, which is more inward than my innermost self and which models our thoughts accordingly. Such extimate activity as defined by Lacan is the formal condition for the construction of visibility and is inscribed into contemplation. The article postulates that this fundamental discrepancy was also the foundation upon which Hegel carved a positive determination of thought.