It is definitely easier to write about work when things are going well, but it is even more important to write about what happens when things get challenging. The act of writing about the challenging times can be challenging in itself but can also provide invaluable insights into the process of teaching: important for the writer and just as important for the reader. This section includes stories of tricky situations, emotions running high, and what kinds of things the teaching artist did to get through the hard bits. [For the rest of the articles in this series: I: Making Art, see EJ1039315; II: The Bigger Picture, see EJ1039319; III: Trying Something New, see EJ1039323; and V: Musing, see EJ1039274.]