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Conducting qualitative interviews in the field can be challenging for anyone, but for inexperienced interviewers, there is a steep learning curve. While performing interviews with trans folx about their experiences with the criminal justice system, one of my interviews went askew when my participant refused to choose a pseudonym despite my explanation concerning confidentiality. My participant did not break eye contact as they leaned forward and stated into my recorder their real name and said that I, April Bennett had explicit permission to use their name. I knew at that moment if I were to repeat my protest about the pseudonym I would lose the interview, so I backed down and tabled it for a discussion with my mentor. This was a hard lesson in adaption. When I first entered the field I quickly realized I was not nearly as informed as I perceived, but with the help of knowledgeable community members, I have received invaluable guidance. During the roundtable discussion, these are the types of lessons I wish to share from my own experience as well as discuss how being in the field can be both challenging and rewarding.