An Essay about a Commonplace book assignment I wrote and tested in 2012 (published in Journal of Interactive Technology & Pedagogy in 2014) and have since revisited and reflected upon. The essay goes into more detail about aspects of my assignment that I had not discussed in my earlier, and more practical, publication for JITP––more specifically, the way that its development had animated a kind of existential anxiety within me. As a result, this piece is an idiosyncratic and somewhat personal meditation, one that is as much about the expansiveness and limitations of my pedagogical thinking in the heady, “very online” days of 2013–2015 as it is about teaching Shakespeare or early modern book history.