This essay describes how environmental conditions affected my unexpected evolution from farm life in a rural Canadian community to becoming a physical education specialist and multisport coach and eventually a U.S. kinesiology scholar with a public health focus. I first recount my life on the farm and initial education and then identify the importance of full- and part-time jobs relative to how they helped prepare me for a life in academia. Later, I summarize two main areas of academic work that extended beyond university campuses—the design and implementation of evidence-based physical activity programs and the development of systematic observation tools to assess physical activity and its associated contexts in diverse settings, including schools, parks, and playgrounds. I conclude with a section on people and locations to illustrate the importance of collaborations—essential components for doing field-based work. Without those connections, I would not have had such an extensive and diverse career.