We propose to design a Custom Learning System that responds to the unique needs and potentials of individual students, regardless of their location, abilities, attitudes, and circumstances. This project is intentionally provocative and future-looking but it is not unrealistic or unfeasible. We propose that by combining complex learning databases with a learner’s personal data, we could provide all students with a personal, customizable, and flexible education. This paper presents the initial research undertaken for this project of which the main challenges were to broadly map the complex web of data available, to identify what logic models are required to make the data meaningful for learning, and to translate this knowledge into simple and easy-to-use interfaces. The ultimate outcome of this research will be a series of candidate user interfaces and a broad system logic model for a new smart system for personalized learning. This project is student-centered, not techno-centric, aiming to deliver innovative solutions for learners and schools. It is deliberately future-looking, allowing us to ask questions that take us beyond the limitations of today to motivate new demands on technology.