On Friday, December 11, 2020, I had the privilege of moderating a roundtable discussion entitled Teaching Challenges. It’s a title that not only nods to the challenges we face while teaching, but perhaps, also to the challenges we present to our students. It was the last roundtable of the superb Teaching Life Writing Conference, which had injected much needed excitement and intellectual stimulation into a daily routine that can only be described as a dystopian groundhog’s day. In that vein, we forged ahead in fellowship with other life writing scholars and explored, listened to, and even commiserated over our shared teaching challenges. Scholars Li Shan Chan, Dr. Kylie Cardell, Dr. Natalie Edwards, Dr. Christopher Hogarth, and Dr. Desirée Henderson presented teaching strategies and lessons from their experiences of teaching. Li Shan Chan began the discussion with a frank and honest conversation between her and her autobiographical subject. She reminded us of the importance of humanizing our subjects, instead of treating them like sources of research. Next, Kylie Cardell presented her experiences of teaching shorter biographical works like the Rebel Girls book series, which not only offers brief, light-hearted stories for maxed-out undergrads (and perhaps, also profs), but also online activities that extend beyond the classroom. In concert with Cardell’s shorter texts, Desirée Henderson, who presented last, also found success in teaching short diary fictions that touch on identity, sexuality, and trauma. For Henderson, diary fiction fills in gaps, possessing the potential to provide context for archival silences since the role of diary writing has the potential for adding to archival knowledge. Her focus on diaries related to Natalie Edwards and Christopher Hogarth’s presentation on researching French migrants who penned life writing in Australia. They rounded out the roundtable by sharing their experiences of using literature in their French language classes, which not only strengthened foreign language acquisition skills and literary competency, but it also highlighted the layered identities of migrant writers reflecting on their cultural roots alongside their new Australian surroundings. The conversation was rich, particularly as we speculated on the rise of diary scholarship – a popular topic emerging in this year’s list of newly published books. Many questions during the roundtable surrounded the marginalization of diary fiction and the reasons for increased diary study. Other questions contemplated student reader reception regarding shorter, more consumable texts, and the tension between nonfictional and fictional works in the classroom. But, my favorite comments and questions emphasized process, not product, thereby, drawing attention to the development of ideas and projects as opposed to their completion. In all, it was a compelling conversation that took place during the last session of the last day of what would become a truly memorable conference and experience.