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Imagination capacity is proposed as a potential core capacity for teaching, leading, and learning in complex contexts. An interpretative phenomenological study explored narratives of teachers, students, and teaching artists to yield a model of imagination that showed congruence to complex adaptive processes with the added quality of agency. Teachers with imaginative capacities can work in creative-adaptive ways to lead and nurture similar mindsets in their students, thus equipping them with the ability to flourish in futures we are unable to predict. This model of imagination comprising dynamically interacting capacities of Flexibility, Openness, Persistence, and Rigor is offered as a critical capacity for flourishing in the emerging, complex postmodern economy where change is the only constant we can be sure of.