This chapter will cover the challenges of starting and completing a master’s level counseling program. Obtaining a graduate degree in counseling can have its benefits. However, its pursuit also comes with scholarly, personal, emotional, physical, spiritual, as well as financial challenges. As more diverse students share interest in graduate studies, it is important to include methods that ensure that cultural and professional needs are met at the chosen institution. But before we consider the challenges, an individual from any background must consider two major components that lead to success in a graduate program. The first component involves student motivation for entering the counseling field. The second major component for graduate school success is assessing the resources that the prospective student needs. As an extension of this conversation, this chapter also looks at how important understanding one’s attachment style and engagement in self-care can impact the student’s graduate experience. In conclusion, content will not only discuss the obstacles facing graduate-level students but also offer various ideas for successfully navigating these obstacles and offer insights for moving from academia to the professional field.