The new U.S. national standards movement has pushed us at “warp speed” from Common Core curriculum standards to updated assessments for college readiness, but we have not fully examined what it means to be college ready. Why is it that roughly half of all high school students need remedial classes before being considered ready for college-level work? Current public policies aim to eliminate the need for remedial college classes by ratcheting up instruction and expectations at the K-12 level, but if we do not find out what these students are missing, how can we expect to be successful? For higher education scholars and practitioners and those generally interested in the future of college, this book helps tell a novel story about the transition to college, from the perspective of an experienced college professor. The first-year experience is conceptualized as a two-way relationship between students and colleges, involving introductions, resistance or acceptance, collaboration and exchange of ideas, and learning. There are both success stories and stories that end in a parting of ways. These stories show what college readiness really means and offer valuable insights about the academic, social, monetary and other forces that can overwhelm the typical college-bound student. Higher education scholars and professionals will benefit from these rich and detailed accounts as they help shape the landscape of 21st century college readiness.