The digital revolution is impacting enormously on the way we create and undertake business. To keep pace and navigate the complexities of this incessant evolving state requires entrepreneurial thinking capable of moving us from the old to the new. An often-overlooked aspect of this transition or change process is the space that lies between the old and the new, a betwixt and between state, fuelled by opportunity, but clouded in uncertainty and ambiguity. In this article, we stress the significance of this between space and discuss the importance of liminal thinking as pivotal in navigating the passage from old to new. We do this by drawing on the concepts of liminal space and liminal thinking, illustrating how these concepts can be deployed to reconstruct reality in such a way that stimulates the crucial cognitive recalibrations needed to cross the passage from old to new. To know that this ‘betwixt and between’ space exists, to recognise the qualities of this space and, most importantly, to manage it, is invaluable in entrepreneurs’ dynamic, rapidly changing world.