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As an increasing number of middle schools explore personalized learning (PL), there is an urgent need for empirical research that can be used to inform teaching and policy in this area. Student perspectives are also underrepresented in research on PL, although this approach is purported to benefit them. This study uses qualitative inquiry to investigate middle school student experiences with making choices in how they learned during a PL project. Findings indicate that choice making was associated with increased confidence in choice-making, new self-knowledge, and learning efficiency. Choice making was also accompanied by feelings of uncertainty as students grappled navigated their unique learning process. We subsequently offer implications of these findings for both middle school education and future research.