The increasing availability of self-monitoring technologies has created opportunities for gaining ­awareness about one's own behavior and reflecting on it. In teaching and learning, there is interest in using ­self-monitoring technologies, but very few studies have explored the possibilities. In this paper, we present a design study that investigates a technology (called Feeler) that guides students to follow a specific learning script, monitors changes in their electroencephalogram (EEG) while studying, and later provides visualization of the EEG data. The results are two-fold: (1) the hardware/software ­prototype and (2) the conclusions from the proof-of-concept research conducted with the prototype and six ­participants. In the research, we collected qualitative data from interviews to identify whether the prototype supported students to develop their reflective skills. The thematic analysis of the interviews showed that the Feeler's learning script and visualization of the EEG data supported greater levels of reflection by fostering students' curiosity, puzzlement, and personal inquiry. The proof-of-concept research also provided insights into several factors, such as the value of personal experience, the challenge of assumptions, and the contextualization of the data that trigger reflective thinking. The results validate the design concept and the role of the prototype in supporting awareness of and reflection about students' mental states when they perform academic tasks.