In this chapter, we share some approaches for leading projects at the edge of chaos, the ﬁ ne line between order and disorder. We address the reality that the highly systematic approaches of project management can break down when we apply pressures of uncertainty, complexity, and stretched resources. Some of our approaches for leading projects at the edge of chaos are borrowed from the world of information technology project management, more speciﬁ cally the world of agile project management. Other approaches come from lateral thinking, structured techniques for identifying both intended and unintended consequences in complex global projects. Ultimately, one of the strongest approaches for dealing with complexity is to simplify. We deﬁ ne simplicity as the art of deciding what you don ’ t have to do and then committing to not doing it. Implementing this type of simplicity is somehow not so simple for most organizations.