This chapter explains why Buddhist and Taoist Systems Thinking is more relevant today than ever (for organizations and entrepreneurs that are transitioning to the new business paradigm), and what potential contributions can bring to sustainable management. The arguments are grounded in three core ideas. First, it illustrates how the modern application of Taoist fundamental principles that have long been missing in the science and practice of management (the East–West knowledge gap) can help guide the sustainable transformation. Second, it argues that Taoism and Zen Buddhism, its perennial foundational philosophies of the Axial Age, are pioneering and unique in developing a systems body of knowledge. It is based on the ideas of constant change and adaptability to complex (and apparently contradictory) environments and phenomena. Third, the concepts are contextualized within the emergent VUCA world (volatile, uncertain, complex and ambiguous). They are updated and adapted to help contemporary organizations deal with the increasing convergence of the physical, biological and virtual domains that condition the way business and labour is, and will be, understood and practiced.