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This study investigates how the transition toward self-direction is experienced and facilitated in 2 semester-long courses in teacher education degree programs and the differences in such a transition for freshman and master’s students. The thematic analysis of the written self-assessments of 8 illustrative examples enabled the detection of (a) students’ initial upset in the face of demands for internal authority; (b) the support of the teacher and peers in managing that upset; and (c) the students’ shift toward more complex conceptions of learning and teaching, including evidence of increasing self-direction. These findings shed light on the potential of intentionally designed learning contexts for promoting students’ epistemological development. The similarities found between freshman and master’s students’ experiences when managing the demands of internal authority emphasize the underutilization of the most extended teaching practices in higher education.