When learning a classical instrument, people often either take lessons in which an existing body of “technique” is delivered, evolved over generations of performers, or in some cases people will “teach themselves” by watching people play and listening to existing recordings. What does one do with a complex new digital instrument? In this paper I address this question drawing on my experience in learning several very different types of sophisticated instruments: the Glove Talk II real-time gesture-to-speech interface, the Digital Marionette controller for virtual 3D puppets, and pianos and keyboards. As the primary user of the first two systems, I have spent hundreds of hours with Digital Marionette and Glove-Talk II, and thousands of hours with pianos and keyboards (I continue to work as a professional musician). I will identify some of the underlying principles and approaches that I have observed during my learning and playing experience common to these instruments. While t...