Graduate students considering constructivist grounded theory as a qualitative methodological approach may benefit from recognizing the many challenges they could face when embarking in thesis work. These challenges include great diversity in approaches to grounded theory, lack of congruity in how grounded theory methodology is described and understood within the literature, and a dearth of expertise and/or support within academic committees and institutions for both grounded theory and constructivist approaches to qualitative research. In this article, we describe why we selected constructivist grounded theory for our PhD work and the common challenges we encountered. Drawing on the analogy of preparing for a journey, we offer strategies for future graduate students including locating one’s ontological and epistemological worldview, finding grounded theory mentors, and facilitating a methodological fit with academic stakeholders. Our recommendations focus on how to navigate the challenging terrain of conducting a qualitative research project within a predominantly post-positivist landscape.