A mismatch between enrollment and completion persists in higher education. This issue is particularly troublesome in the community college sector. Of the factors attributed to the decline in college completion are student transitions across institutions, particularly articulation and credit transfer. This is especially significant as students are gradually deviating from a singular, linear pathway through higher education. Yet, empirical work explaining student movement, specifically among community college students, is limited. Moreover, theoretical and conceptual work explicating students' higher education choices tend to focus on students making their initial decision to enroll in higher education. Through a combined grounded theory and narrative inquiry approach, this study drew upon interview and survey data to construct a contextualized model explaining how community college students, once enrolled, further choose among competing postsecondary pathways. Findings reveal that these students' decisions fell into two broad categories: lifetime and short-term. There were five factors that emerged from these categories. In order of significance, they were: payoff, fit, portability, mobility, and flexibility. The nuances of the factors are explained and further illustrated through students' narratives. The findings highlight the wide range of student pathways, not only within higher education, but also outside of it, thus pushing practitioners, policymakers, and researchers to rethink success and completion in the context of community colleges and divergent student pathways more broadly. This study is additive toward research, theory, and practice on college choice, navigation, and success among community college students.