The process of becoming a qualitative researcher is fraught with challenges that are not always knowable prior to engaging in research. Coursework, reading, discussions, and writing about the process provide a foundation but cannot replace the experiential value of engaging in research. This autobiographical intrinsic case study describes the author's first attempt conducting qualitative research as a doctoral student documenting additional challenges after the participant, my mother, was diagnosed with terminal cancer. Using document analysis, I chronicled and made meaning of this first experience, especially how my relationship with the participant impacted my understanding and applying the concepts of rapport, reflexivity, subjectivity, and intersubjectivity.