Liberal arts pedagogy, characterized by its emphasis on adaptability and breadth, thrives on the input of fresh perspectives; arguably, it requires them to maintain its relevance. In this paper, I engage theoretical and applied scholarship on improvisation pedagogy to illustrate how integral improvisational thought is to the spirit of the liberal arts. Considering the liberal arts ‘toolkit’ as, essentially, that of an improviser—a rounded, context-dependent and hybridizing approach that is well-suited to novel and sometimes unforeseeable scenarios—reaffirms the liberal arts’ value in the shifting academic climate of the 21st century, in which such skills are increasingly necessary. In order to explore that potential, I synthesize the foundational works of Lev Vygotsky, Stephen Nachmanovich, and Ed Sarath with newer scholarship on 21st century education.