This article describes my tumultuous journey as a course instructor and researcher investigating imagination in an educational leadership graduate seminar. I employ an arts-based pedagogy and research methodology known as Performative Inquiry. Sharing my experiences delivering this course informs my future teaching and can support colleagues interested in exploring imagination with their students. I accepted risks associated with arts-based performances and entered a shared space of vulnerability with my students. My struggles with resistance were real, and so too was the realization of the important role vulnerability plays in imagination-focused (leadership) education. I suggest that Performative Inquiry offers other (leadership) educators a powerful pedagogy and methodology for understanding imagination in their own lives, nourishing their imaginative capacities, and inquiring into their leadership education practices. Arts-based practices allow learners to feel their own imaginations and experience possibility by accepting invitations to be vulnerable and performing learning in a range of productive and generative ways.