The circular economy describes an economic model characterised by value maximisation of natural resources through retention, recovery, and regeneration of consumed products for maximum product life and usefulness. Circularity appears to be an admirable solution to the wicked problems humankind faces due to prolonged unsustainable behaviour. However, the circular economy can only be achieved by overcoming multiple impossibilities. System leadership is a leadership model in which influence is exerted beyond the leader’s sphere of influence, enabling the person to influence across entire systems. System leadership is appropriate for achieving sustainability and overcoming the impossibilities of achieving economic circularity. Leaders who understand and influence entire systems and their actors by extending their influence beyond existing organisational, geographic, and political boundaries are needed to overcome the impossibilities of the circular economy. In this chapter, we will explore the development and application of system leadership as a method for overcoming the impossibilities of economic circularity.