"Sounding for Cool" is about self-transformation, about growing up on one's own as a product of contemporary America, and about how to become not just a man, but a contributing adult in society. Donald Morrill presents the day-to-day lives of seven young men (white, black, Hispanic, immigrant, middle-class, thick-headed, poor, and smart), who for various reasons have become homeless. Placed in a Transitional Living Program facility (TLP) by the courts, these men must learn to navigate in the world of "normal" values and reasonable rules. Streetwise and callow, trained to seek shortcuts or to make excuses, they struggle with the structures and assumptions inherent in living a law-abiding, bill-paying life. While sorting out their souls, they learn how to connect with others.

In turn, "Sounding for Cool" scrutinizes the staff of the TLP, one woman and three men, who variously come to terms with their lives by settling accounts from the past. As a TLP volunteer, Donald Morrill often finds himself bridging the gap between staff and client. In the process of telling their stories, he chronicles his own journey to understand the past. Ultimately, Sounding for Cool asks the enduring questions, "Who am I in the world and what can I become?"