Society seems increasingly complex, in part due to constant “breaking news,” likes, tweets, etc. Considerable change is being entertained, or at least debated. Significant decisions are required. Decision making lately has been flawed, laced with contention, hesitancy, and poor outcomes.The author has long helped clients and sponsors to understand complexity, address needs for change, formulate plans, and make decisions to invest resources to execute these plans. His engagement with them has focused on formulating problems, devising possible solutions, and deciding which solutions merited investment.This book represents the author's reflections on these engagements, associated challenges, and typical outcomes. These stories are reports about clients or sponsors’ problems and how he and his colleagues went about addressing these problems of complexity, change, and decision making.The clients or customers for these services included over 100 enterprises in industry, government, and academia. Most were large, many in the US, but quite a few were in Europe, Asia, Africa and Latin America. Geography mattered in these engagements, but did not dominate.The chapter in this book represent his reports on what he learned, and what he could generalize across airplanes, automobiles, banking, computers, communications, insurance, pharmaceuticals, retail, satellites, semiconductors, and telecoms, working with stakeholders from companies, agencies and academia.