A growing number of institutions undertaking "guided pathways" reforms are rethinking how students select programs of study, choose courses, and make other program-related choices. One primary aim is to help students make thoughtful decisions about their programs early on as a means to encourage faster and more satisfying college completion. The City Colleges of Chicago (CCC) has been undertaking a guided pathways reform effort for several years. Based largely on student interviews, this paper describes how degree-seeking students at CCC make choices about their programs in their first year of enrollment, focusing especially on how they interact with advisors and how they use college-based resources in program selection and program planning. We find that the complex process of program selection and planning is undertaken differently by students with greater or lesser tolerance for ambiguity, and that inconsistent or conflicting information about program details is particularly frustrating for some students. We recommend that institutions engaging in guided pathways reform efforts clarify advising processes and materials to reduce contradictory information and confusion.