Currently, there is little in-depth understanding of how individuals effectively orchestrate school and work-related experiences over time from high school through college and beyond to pursue careers in Science, Technology, Engineering and Mathematics (STEM). This appears important because, unlike societies such as Germany, youth in the U.S. face an almost complete lack of structured pathways from school to work. Presently in the first year of a two-year project, this study uses a mixed methods approach to address a set of research questions from a wide variety of perspectives, and works toward developing an integrated synthesis of the important factors in this process. This study deals with the human systems that underlie all other systems, as well as those human systems' interactions with other types of systems that may range from mechanical to socio-cultural systems.