When design students encounter the ambiguity inherent in the design process, it can cause stress, anguish, and feelings of inadequacy. However, these experiences of failure, dead-ends, and “stuckness” are often the ones in which students learn the most about designing. By prompting regular reflection on encountered challenges, students can reframe their attention, not on simply designing projects, but on learning how to design projects. This study compares reflective writing assignments and their effects in two contexts; a first-semester design studio and a final-semester architecture studio. These assignments seek to place the metacognitive processes necessary for independent design work (monitoring, evaluating, and planning) on equal footing with the cognitive and physical work produced in the studio classroom. To achieve this, the mental work behind the physical work is regularly recorded and discussed as part of the projects. Journals serve as a record of design intent, of feedback and responses to it, and of personal growth. Furthermore, they provide a platform for dialogue through which students can begin to see design challenges differently. “Stuckness,” for example, is often perceived as a private, personal problem indicating a lack of talent. Through discussion, it can be reframed as a common experience that designers share, one which can be overcome through various strategies. Metacognitive writing can have powerful effects; in comparison with students from past years, students who completed the newly introduced reflective writing assignment were more likely to develop critical friendships with their peers and face design challenges with more confidence and resilience.