Transitions can be destabilizing and difficult. By understanding how graduate students ages 22 - 26 perceive the process of transitioning into student affairs masters-level preparatory programs, professional and personal developmental interventions, programs, and services can be better designed to assist them. The present phenomenological study explored the perceptions of students entering two student affairs M.Ed. programs as they oriented toward graduate study and how they made meaning of their experiences in their own words. Goodman, Schlossberg, and Andersons (2006) three-phase model of adult transition served as the theoretical framework. Students were recruited from two student affairs programs housed at public institutions located in the same state in the Southeast. Data were collected from eight participants through reflective essays and interviews at three intervals from August 2011 to January 2012. Data were analyzed according to Giorgis (2009) descriptive phenomenological method in which meaning units are identified, clustered, and analyzed to uncover the essential constituent elements of the phenomenon. Findings from the study include that students were too preoccupied with relocation and acclimation issues, as well as starting coursework and learning the requirements of their program, during the first several weeks of the semester, to think about the larger picture and professional development. If the purpose of a masters education is to receive focused professional education in ones chosen career path, then the most efficient way to assist them on their path to professional development is to concentrate efforts on alleviating the stressors of the first several weeks. Second, this study calls into question the notion of similar past transitions being indicative of future ones as these eight students found that the main strategies they had employed in their transition to college were no longer feasible. Third, the data revealed that making connections with others was crucial and that the connections themselves often mattered more than with whom students connected. Finally, there is a discussion on what it means to move out of a transition and how this may look different for underrepresented populations.