Leadership and its definition is on a continual evolution that is often no more than exchanging one outdated characteristic (goodbye “Charismatic Leadership” ‐ the idea that one figurehead inspires and directs the company) (Vergauwe, Wille, Hofmans, Kaiser, & De Fruyt, 2018) for more progressive examples, (hello “Servant Leadership” ‐ the idea that the purpose of leaders it to serve those who deliver the ‘product’) (Linuesa‐Langreo, Ruiz‐Palomino, & Elche‐Hortelano, 2017); without fully explaining the transition. Partly due to the newness of the field compared to other academic disciplines, and partly to the acceleration of business behavior; academic and business definitions of leadership seem to be struggling to keep pace. The current article presents evidence to support a more enduring lens of leadership, with particular attention to leadership definitions from Taoism and contemporary texts that describe the Tao. In the context of “second‐tier” leadership, a relatively modern concept, it suggests approaches to the attainment of the Tao style may be another route to a post‐conventional worldview more applicable in the modern age. The future‐proof leader has a greater capacity to wrestle the complexities of the modern world (Kegan, 1994) and take multiple perspectives on any given problem. Future‐proofed “wise” leadership is agnostic of the change speed of technology, yet the momentum of technology, globalization, and instant communication are what makes its understanding a modern necessity.