This chapter argues that approaches to navigating complex world making and transformative change for sustainability are more effective when they are anchored in a profound understanding of life processes. The chapter takes the concept of systems aliveness as a quality element of a pattern approach one step further. It advances 13 propositions regarding essential features of life enhancement in systems that can also inform a better understanding of enlivening human co-creation. The propositions lay the basis for the Patterns of Aliveness Theory, which shows how six essential organizing principles allow life to emerge, thrive, and re-create itself in natural as well as social systems. The chapter suggests that these principles must be taken into account in the practice of leading collectively and shows how they become the foundation of a conceptual architecture for stewarding sustainability transformations.