This paper considers business and enterprise education through the lens of theatre and the creative arts, and identifies new pathways towards an interdisciplinary way of supporting the young innovators of the future, placing higher education as a central catalyst. Following a review of key criticism directed at traditional business and management approaches in the academy, the article problematizes the notion of experiential enterprise education in the curriculum and poses the question as to where and when students are afforded the opportunity to fail. Through an autoethnographic account, the key themes of authenticity, risk and failure, experiential approaches and embeddedness are presented. There is an urgent need for further and higher education institutions to develop a much more holistic and interdisciplinary approach to developing entrepreneurship in their students. These institutions are currently perpetuating pedagogical hypocrisy in that they preach productive failure while practising assessment success. An effective 21st-century approach would champion risk-taking and productive failure, place processes over outputs and acknowledge the important role of the post-course curriculum.