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Postsecondary experiences for high school graduates, in vocational training, college coursework, and workplace opportunities, increasingly require applicants who exhibit “deeper learning”—graduates who are creative problem solvers with collaborative interpersonal skills. Concurrently, policymakers are revising diploma expectations to include apprenticing within internships. What kinds of classroom-based experiences prepare high school students with the dispositional, social, and academic knowledge and skills needed to engage successfully in apprenticeships? This investigation examines the Study of Deeper Learning English language arts student work data set for evidence of project-based learning processes (i.e., real-world applications, iterative learning, student-student collaboration, disciplinary content/skills, mastery learning) so as to consider how ambitious classroom-based assessments and performances of learning offer rehearsal for school-connected apprenticeships and skills needed for postsecondary success.