What is it like to do qualitative research for the first time? Given that the assumptions for quantitative and qualitative research are quite different, switching to conducting qualitative research can be a rather steep learning curve. This chapter is written with two primary audiences in mind: (1) quantitatively oriented scholars who are considering or beginning journeys into qualitative research, and (2) those who have been working in qualitative areas but who would like to consider the journeys they and others have taken into this arena. We explore the process of conducting qualitative research from the vantage point of those who came to qualitative research after being trained in quantitative methods. To do so, we interviewed several such scholars and focused our findings around five key themes: surprises encountered while learning qualitative research; differences between scholars’ quantitative training and qualitative inquiry; things they had to “undo” or “relearn” from their quantitative training; what they wish they had known when they started qualitative research; and advice for others (especially newcomers) for conducting high-quality qualitative research. Throughout the chapter we also provide our own reflexive insights into these challenges and processes.