We present the Personal Learning Environment (PLE) as a practical intervention concerning the organization of technology in education. We explain this by proposing a cybernetic model of the “Personal Learner” using Beer's Viable System Model (VSM). Using the VSM, we identify different regulatory mechanisms that maintain viability for learners, and how physical engagement with tools is of fundamental importance in learners being able to manage their learning environment. We explain how the PLE, in exploiting Service Oriented Architecture, attempts to address this issue of the engagement with tools by allowing learners to control their own instrumentation. This, however, is more than a practical issue. In shifting the locus of control over learning to the learner, the ways in which learners exercise that control becomes an important educational issue. Drawing on sources ranging from Bandura's work on self-efficacy, and philosophical work on social ontology, we argue that self-regulation and technological personalization are issues which strike at the heart of current debates about the organization of education and the nature of the relationship between institutions and learners, and more deeply, the human condition in the modern world. Some anecdotal practical implications are reported in the final section of the paper as we describe the response of learners to the challenges of increased personalization.