Leadership writing draws strongly from rational and unitary conceptions of self. Within leadership-texts self is rarely presented outside of analytic philosophical traditions. Such modern assumptions of self suffer little effective challenge within academic management disciplines. If the ‘truth’ about the individual has been lost amongst ‘leadership facticity’ then can it be recovered by leadership learning beginning to explore an interface with the indirect and long-structures of thought within other forms of expression; such as represented by the ideas in modern and contemporary literature? The extent and depth of self in these ‘artful’ literature characterisations potentially offer a more enduring revelation of self. These new meanings are then a varied departure point for ‘leadership’ discourse; suggesting that leaders’ and managers’ views of ‘self’ are re-shaped via engagement with immersive artful textual representations of self prior to any question of ‘how must I lead?’. Leaders immersed in these ‘fine’ representations of self may be more intuitive in their understanding. This interface then opens up new lines of enquiry worthy of academic interest; asking major questions about self and how leaders shape conceptions of the human being. Not least it offers a basis for suggesting that the philosophical landscape beneath leadership discourse needs re-framing. This points to a difficult possibility. That leadership itself is reconceived from being an objectified notion embedded within the individual but rather a substance present within the breadth of human discourse, and its textual representations. It implies that leadership should attract no brute facticity but should remain ‘lost’ within textual representation; its very incoherence being its strength. Enquiry in the field should consider turning more strongly to understanding ‘what is self’ through longer structures of writing, such as represented by autoethnographic forms.