Large variations in the knowledge, skills, and interests of entry-level students are increasingly challenging higher education learning designs to support the individualization of learning experiences. To provide pedagogical infrastructure with space for individualization and capable of activating students to take accountability for their own learning, a flipped-learning environment to support students' self-regulative learning was designed. This study focuses on learning goals and students' use of a semi-structured learning diary—an important part of the pedagogical infrastructure. Based on their entry-level content knowledge, students were divided into novice and advanced learners to understand differences in their diary keeping and learning performance. Qualitative analysis of the learning diary entries showed that the diary, scheduled to facilitate starting and completing flipped-learning tasks, systematized students' setting of learning goals and reflections on goal attainment. Novice and advanced students alike were active in setting individualized and well-founded learning goals. Comparisons between novice and advanced student groups suggest that when approximated by setting individualized learning goals and reflections on goal attainment, self-regulative performance is independent of disciplinary expertise. That is, the differences between the two groups were smaller than those between individual students. However, situational and contextual factors such as task-type or character of the subject could also have an effect on actualized performance. The results suggest that learning designs need to consider individualizing support for content and self-regulation.