The transition from oral tradition, to hand-written manuscripts, to the printed word, has had many forks in the road, resulting in countless paths not taken. Exploring the forgotten options, such as the letterforms of the Benevetan script, gives us new perspectives on our present. While this article is strictly within a typographic context, it takes on additional meaning reading it from the perspective of someone familiar with the AI revolution. We are at a point in human history where we may be undergoing another transition, from the writing and printing/display of human-written words, to the those generated by a computer. There are many choices being made right now creating a fractal landscape of "paths not taken" for the future.