This book retrieves and builds upon some of my essays addressing issues about the changing face of law, lawyering and legal education over the last 30 years. Those issues were, of course, canvassed by others in their own way during this period. But, each of us comes to them through a unique set of experiences in a distinct set of institutions whose members made assumptions about those institutions. My experiences, not least in my interactions with those institutions and assumptions,1 provided important insights and influenced the way I addressed those issues. Like all such experiences, they can provide insights that others miss. As well as providing an introduction to the contents of this collection, this chapter provides a narrative of my journey through those experiences and assumptions. In so doing, I hope to explain some of the insights generated and present a case-study about how legal academia shifted over time, and one person’s role in that shift: helping instigate it even as I was living within the constraints of a dynamic environment.