Learner-centered education has been touted as an improvement over teacher-centered educational systems. However, educators and researchers need to be cautious about its problems, in addition to considering its benefits. The authors set out to identify challenges to learner-centered education through the eyes of educators in a truly learner-centered school with a self-directed, project-based learning approach. During their interviews, three administrators and all nine teachers described challenges that they faced in learner-centered instruction and learner-centered assessment. The hope is that the study makes learner-centered education easier for educators and more effective for students.