Long-distance truckers are the lifeblood of complex supply chain networks. Thus, it is important to analyze ways to enhance the efficiency and effectiveness of these professionals. In particular, what factors contribute to their job satisfaction, quality of life, and overall success? These questions are partially answered in this study using the framework of appreciative inquiry to construct a comprehensive sketch of the day-to-day lives of long-distance truckers. While other aspects of the supply chain have been studied extensively, relatively less research has been directed toward understanding the nuances of the trucking way of life. The current paper offers some partial solutions, research directions, and managerial guidance.