I built an automated math learning system called Mathewmatician's Dictionary, and the deeper I went, the more it stopped feeling like an education problem and started looking like a software design problem. Three lessons carried over directly. First, when a student fails a topic, the real cause is almost always an unmastered prerequisite several chapters back, the same way a UI bug often lives in the data layer. Concepts have dependencies, like a build graph, so I stopped organizing learning by ...