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What can one educator’s journey tell us about how education itself has changed? Fourth-year principal Jason Eldredge joins High School Transcript to reflect on a career that has taken him through elementary, middle, and high school education. We discuss the evolution from paper-heavy classrooms to an increasingly digital landscape, why some educators are beginning to reconsider pencil and paper, and what those shifts may mean for student learning. We also dig into questions surrounding college readiness, including recent findings about high-achieving high school students requiring remedial coursework after graduation. Along the way, Jason shares the experiences that shaped his path from educator to administrator and his perspective on where education has been and where it may be heading.