In this autoethnography, I explore a teaching failure I experienced during the onset of the COVID-19 pandemic. I illustrate how this failure was exacerbated by my precarious position in the academy as a new biological mother and a pre-tenure faculty member. I specifically explain the guilt I felt as a professor, how my attempts to eradicate it backfired and contributed to mom guilt—the feeling that I was not doing enough as a parent or a partner—and what I learned from this failure to enhance my pedagogical practice through the implementation of feminist pedagogy.