An important mandate of higher education is to provide students with the skills and strategies required to become self-regulating lifelong learners. This paper analyzes and interprets data gathered from two instructional settings both of which have been structured to promote self-regulated or self-directed learning. It includes an interpretation of a series of discussions with medical students regarding their impressions about what makes the problem-based learning (PBL) environment successful and juxtaposes this with experiences related to promoting self-regulated learning through the strategic content learning (SCL) approach. The practice of PBL and SCL are examined in order to provide insight into how a collaborative learning environment can be orchestrated so as to simultaneously promote self-regulation, lifelong learning, and mastery of the core curriculum. The findings are interpreted using a theoretical framework based on notions of learning in a community and implications for the way in which participants learn to orchestrate and contribute to a community of learners oriented toward self-regulated learning and practice are discussed. Findings indicate that building a community of learners who are involved in strategic self-regulation requires careful orchestration on the part of the instructor. Contains 27 references. (JRH)