This chapter highlights environmental trends in the socioeconomic climate and in higher education, focusing specifically on the Baby Boomer demographic. It demonstrates how older students remain underserved in research, and develops a compelling case for further research to be conducted focused on non-traditional aged students (namely, the Baby Boomers). These claims are supported by the analysis of survey data, which contributed to the development of a decision model about factors which influence Baby Boomers' decisions to return to school. There is discussion of what decision-making alternatives exist when selecting traditional or online delivery of education. Framed with decision-making research from the fields of psychology, anthropology, and pedagogy, this study draws links to contemporary decision-making theory. The decision model and discussions in this chapter address the knowledge gap in the literature about non-traditional aged students and provides key insights towards attracting and enrolling students from this cohort.