Labyrinths and mazes have constituted significant spaces for tales of transformation, from prehistoric designs through the myth of the Minotaur and the pilgrimage design in Chartres cathedral to contemporary novels and pictorial representations. Labyrinths and labyrinthine designs can also commonly be found in present day organizations. This text, based on an ethnographic study as well as on an analysis of academic discourse, explores their significance as a symbol and as a physical structure. Drawing upon the notion of transitional space, it presents labyrinths as an indelible part of human experience, an archetype, and a sensemaking tool for understanding and explaining organizational complexity. The unavoidable presence of labyrinthine structures is presented as a counterpoise to the reductionist tendency towards simplification, streamlining and staying on-message, allowing or demanding space for reflection, doubt, and uncertainty.