Just as the information age ushered in a new set of skills and modes of thinking needed to thrive at work and in life, the dawn of the AI age is catalyzing yet another dramatic reshuffling of the knowledge paradigm. AI’s rapid development as an expert in many disciplines increases the importance of lateral thinking and elevates the abilities of generalists who can work across traditional disciplinary boundaries. This presentation explores how storytelling embedded in learning contexts can help people develop lateral thinking and the kinds of skills needed to collaborate effectively with both humans and machines.