This paper addresses the project of philosophical autobiography, using two different perspectives. On the one hand, the societal, economic, and family contexts of William James are addressed, and connected a modern academic context of business ethics research, marketing and purchasing decision making, and the continuing financial crisis. The concepts of “stream of consciousness” and “acting as-if” are connected to recent literature on William James. On the other hand, the significance of family context, and the possible connection between the William James family and the author, is addressed through shared family narratives interspersed throughout the paper.