Informal learners are taking up educational content online in unprecedented numbers, but these learners often find it difficult to self-direct their pursuits which may be spread across different mediums and study sessions. Inspired by self-monitoring interventions from domains such as health and productivity, we investigate how informal learners can better self-reflect on their learning experiences. We carried out two elicitation studies with paper-based and interactive prototypes to explore a range of designs for capturing and presenting learning data manually, automatically, and semi-automatically. Our synthesis of learners’ perspectives on self-monitoring reveals that automatically generated visual overviews of learning histories are initially promising for increasing awareness. But, users also prefer having controls to manipulate overviews through personally relevant filtering options for better reflecting on their past, plan for future sessions, and communicate with others for feedback. Our findings have several implications for designing learner-centered self-monitoring tools, especially for informal learning settings.