Why do some master's level students feel confident in completing their programs and some do not? Why do some feel connected to their department and some do not? Why do some feel legitimate as graduate students and some do not? This research proposes that there may be differences in how master's students understand the graduate student role based on whether they went directly from high-school through their bachelor's to their master's, or if they took time off between their bachelor's and master's program. This thesis used in-depth interviews with twelve second-year master's students at Portland State University to explore these questions: six with students who had a linear trajectory through higher education and six with students who had a break after completing their bachelor's and before returning for their master's (broken trajectory students). Students from both groups began their programs with questions about their ability to perform at a master's level. Broken trajectory students were more likely to have thought through their chances of success and entered their programs 'knowing' that they would successfully co~plete the programs even when they questioned their academic abilities. Students from both groups overall felt a progressive increase in feelings of connection to their departments. The linear trajectory students entered their programs with some established feelings of connection with other graduate students. The broken trajectory students did not have these established connections, but desired connection with other serious students. Overall, students from both groups experienced increased feelings of legitimacy as graduate students, but the criteria by which they judged their legitimacy differed between groups. Linear trajectory students used academic ability as a primary measure of legitimacy, where broken trajectory students used having a clear understanding of why they were in graduate school as the standard to determine whether they "belonged in college." The two groups also differed in the source of their student role standard: broken trajectory students used professors as their role reference group, whereas the linear trajectory students used peers and undergraduate students. This thesis closes with a discussion of the implications of this research for theory, programs, and current models of persistence.