That computers should be easy to learn and use is a rarely-questioned tenet of user interface design. But what do we gain from prioritising usability and learnability, and what do we lose? I explore how simplicity is not an inevitable truth of user interface design, but rather contingent on a series of events in the evolution of software. Not only does a rigid adherence to this doctrine place an artificial ceiling on the power and flexibility of software, but it is also culturally relative, privileging certain information cultures over others. I propose that for feature-rich software, negotiated complexity is a better target than simplicity, and we must revisit the ill-regarded relationship between learning, documentation, and software.