Do you remember the first time you taught? I do, even though it was over a decade ago. I was so flustered afterwards I rushed to the bathroom to calm down, and inadvertently walked into the men’s bathroom, which only made things worse. You might be wondering, "what happened in this class that was so terrible you rushed out afterwards?" Absolutely nothing. It was completely ordinary. I took attendance and reviewed the syllabus, but as I did so, it dawned on me that I had no idea how to actually teach. All my years as a student had not prepared me for the reality of teaching. What I discovered in the weeks and months that followed that first class was despite my desire to teach, I was not good at it. I could have walked away at that point, and pursued a different career, but teaching had gotten under my skin. So I took pedagogy classes and worked harder on my teaching than I had ever worked on anything in my academic career. Part of the reason teaching is so challenging is that no matter how much you may want to emulate your favorite teacher or professor, what worked in their classrooms may not work in yours, for myriad reasons. You cannot repeat the same motions and get the same results, so you have to learn, through trial and error, what works for you. This chapter traces my journey to figure out what type of teacher I wanted to be, and what type of classroom environment I wanted to foster. My pedagogy has been heavily influenced by feminist and critical pedagogies, along with theories from developmental psychology. It has also been influenced by the nature of my work as a teaching assistant in an English department, a writing tutor, an adjunct professor of writing and rhetoric, and an instruction librarian.