As a professional tutor, author, and speaker for over twenty years, I have come to understand the value of informed, reflective thinking in supporting my student’s efforts to become confident, aware, and self-directed learners. The goal of this synthesis is to develop a larger theoretical framework by integrating what I have learned from my practical work tutoring students with the more formal models of self-regulation that I have begun to study as a student in the CCT Program. When I began my work as a tutor in the 1980s, I was becoming more and more frustrated with the limitations of content tutoring in addressing the needs of the “not so good” students with whom I worked. This led me to develop a variety of techniques that would help me and them evaluate the true sources of their difficulties, so that we could target study intervention in ways more uniquely tailored to their situation. In the process, I became aware of a wide range of “hidden obstacles” that can derail the work of students as well as ways I could begin to help students overcome those obstacles. Without fully realizing it, I was working to help my students become more self-directed learners. When I entered the CCT Program, I was excited to learn more about student self-regulation. Indeed, self-regulation researchers had developed an initial model of self-regulation from a study of the strategies used by “successful” students. Having engaged in the formal study of “self-regulation” through the CCT program, I found myself agreeing with some components of the standard self-regulation model, while also finding it lacking in both scope and depth. First, the model pays far too little attention to the effects of past self-regulation failures on student’s future abilities to self-direct their efforts, while also neglecting to appreciate the continued negative effects of causal mis-attributions and control on student attitudes and behaviors. Such omissions produce a research model of “self-regulation” that is more about “regulation” than “self.” The following synthesis, it is hoped, presents a more practical, comprehensive and in-depth approach to student self-regulation for its intended audience, professional tutors and other educators, who have found the current self-regulation model ineffective for the population of students with whom they work. I credit the CCT program with providing the support, encouragement, and disciplined intellectual guidance needed for me to further refine and synthesize these ideas toward the construct of a more complete and therefore more effective and efficient model of academic self-regulation.