Building on a previous contribution on “negative capability” (Lombaard, Leadership as spirituality en route: “negative capability” for leadership in diversity, Increasing diversity: loss of control or adaptive identity construction? 103–114; 2017) as a non-directive but actively searching and highly influential (Chia and Holt, Strategy without design: the silent efficacy of indirect action, Cambridge University Press, 2009) style of leadership, this paper investigates aspects of the concept of simplicity and its relation to leadership. As management literature has recognised of late, simplicity as a spiritual orientation to life has deep historical roots and various dimensions. One predictable response to simplicity as orientation points to societies invariable complexity. Hence organisations, companies, and almost all human social systems defy attempts at effortless, simplistic illumination. However, niche building within complex systems allow leaders and managers influence. Such influence either aligns interdependent parts of a complex system or distorts the illusions of cheap harmony within it. Here, in these niches, insights and practices of simplicity cultivated in various spirituality traditions may fruitfully be employed. Such insights and practices might steer groups and entities, always awash in entropy, towards coherence, constrained (i.e., strategically guided) action and consistence. Thus, neither social system’s complexity nor their entropy are denied or disingenuously reinterpreted. Rather, they are acknowledged and valued as key operational kernels giving structural stability, strategic progress and conceptual clarity to the whole. In this manner, simplicity contributes not only to the resilience organisations and companies but also to sense-making amongst people involved, namely as a dimension of experiencing fulfilment in life. Examples are provided, and spheres of applicability indicated.