This autobiographical reflection traces my work in land suitability analysis and plan-making. The suitability practice has resulted in two rating systems: the U.S. Department of Agriculture’s Land Evaluation and Site Assessment System and Green Business Certification Inc.’s SITES Rating System. Plans have been made for US counties, cities, and towns; Italian provinces; regions and watersheds; and university campuses. My practice is grounded in human ecology. I have attempted to address the issues people face with an especial focus on environmental quality and social equity. Examples of work from Ohio, Pennsylvania, Washington, Idaho, Colorado, Arizona, and Texas in the United States as well as Italy and Mexico are noted. I explore how reflection, often with collaborators and students, has informed my practice and how it can help advance the fields of planning and landscape architecture.