Early research on just why it might be the case that “the mass of men lead lives of quiet desperation” suggested that denial of relevance was a significant factor. Asking why denial of relevance would be significant and how it might be resolved began to raise issues of the very nature of questions. Pursuing the nature of questions, in light of denial of relevance and Thoreau’s “quiet desperation” provoked a journey of modeling questions and constructing a biography of the initial question of this research and its evolution. Engaging literature from philosophy, neuroscience, and retrieval then combined with deep interviews of successful lawyers to render a thick, biographical model of questioning.