In this chapter, I consider my perspective on the evolution of institutions requiring a terminal degree for the senior-level administrator in higher education and the many considerations needed before choosing a PhD or EdD. There are several reasons why we see HE/SA requiring terminal degrees. These positions are being asked to do more complex jobs with fewer resources, such as developing and implementing student support programs, managing budgets, and working with faculty and staff to create a positive learning environment. A terminal degree can provide students with the knowledge and skills they need to be successful in these roles, particularly the ability to think critically and differently—a key benefit of any terminal degree. There is also a growing demand for qualified and experienced professionals as the student population continues to diversify, and so does the demand for qualified student affairs professionals with more education than the required master’s degree. A terminal degree can make candidates more competitive in the job market and give them a better chance of landing a position in their desired field because they are better suited to meet institutional and student needs. This leads me to my third point.

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