Managing a public school district today has, most certainly, become a labyrinth of elaborate endeavors. Leaders at all levels find themselves pulling on a Gordian knot of processes that were intended to improve schools but have instead become asynchronous, disconnected, and redundant. A school district in Pinedale, Wyoming, has found that taking a systems approach to strategic planning not only simplifies district work but also increases the success of principals, teachers, and students. In this report, the superintendent of Sublette County School District #1, and a senior director at Mid-Continent Research for Education and Learning (McREL), show how a strategic planning process reduces redundancy and workload by integrating district goals, strategic planning, and school improvement into one streamlined process. By establishing conditions for success rather than reacting to problems, this process creates meaningful, sustainable change that results in the ultimate outcome: improved student achievement districtwide.