Stripped to its basic elements, online learning is nothing new. For 200 years or more people have followed remote courses of instruction where learning assignments, materials, and resources came through the mail. You might think the introduction of machines to “program” learning is a phenomenon of the digital age, but Sidney Pressey’s teaching machine appeared almost a century ago in 1924 (Pressey 1950). Nor is flexible, individualized learning a 21st century phenomenon. Programmed learning emerged from innovative thinkers such as B. F. Skinner (1965) and Edward L. Thorndike (1931), who had a vision of self-directed learning through which a highly structured set of tasks were presented. The response the learner made to the stimulus would determine whether they progressed to a new task or some further enrichment or remediation. Thorndike’s understanding of three conditions that maximize learning have formed the backbone of an approach to learning that has endured right through to the 21st century.