Stoicism, philosophy as a way of life and Negative Capability: Developing a capacity for working in radical uncertainty

Philosophy and leadership are not generally held in close association. By contrast, this paper is a call to action for the academy and organisational practitioners to reflect on the potential contribution to leadership of a practice of philosophy as a way of life. In this, we explore what this might entail with an illustrative focus on Stoicism because of its explicit attention to working in radical uncertainty. Recent literature has also identified the potential merits of Negative Capability in this regard, and we discuss how this capacity is closely related to many Stoic practices. We challenge dominant leadership discourses at a fundamental level and argue that there is a need to consider approaches to leadership education and development that go beyond merely gaining new knowledge, skills and techniques. The requirement, which is also an opportunity, is nothing less than a transformation at the level of being and of one’s vision of the world. The theoretical contribution of the paper is supported by empirical evidence from a study with ten organizational executives who were introduced to Negative Capability through an arts-based methodology. This study provides insight into the potential contribution of ideas from Stoic philosophy to the development of a capacity to work with uncertainty. However, a core argument of this paper is that working in radical uncertainty requires more than a ‘quick fix’ and practitioners must learn to develop their own practice of philosophy as a way of life.