The shift in education reform to a goal of college and career readiness for all students is a change that has been embraced widely across the country. The challenge of designing new policies and programs that could accomplish the goal that all students should graduate from high school with the skills and knowledge necessary to succeed in college and career is tremendous. The pressing question now is whether and how students, schools, and the New York City public school system can move this ambitious goal from rhetoric to reality. To help understand this change, the challenge it presents for schools and students in New York City, and the ways in which philanthropy might help move New York City's schools closer to the goal, Philanthropy New York commissioned a set of three papers. This paper, the first in the series, takes a broader look at the context of this reform, beginning with a brief overview of the challenge, both nationally and in New York City. The second section explores the policy context: how we moved from addressing the "rising tide of mediocrity" targeted in "A Nation at Risk," the 1983 report by the National Commission on Excellence in Education, through efforts to raise achievement levels and reduce dropout rates, to this new goal of readiness without remediation. The third focuses on the history and context of the high school--the deeply embedded structures and expectations that make this change so very difficult. The final section looks at current examples of instruments and initiatives underway to measure where we are now, and how to move forward. This section centers on New York City, where over the last decade philanthropies have invested more than two billion dollars in public education, developing many of the innovations that have helped raise the graduation rate, and have begun to advance college and career readiness. [For the second paper in this series, "The Experiences of One New York City High School Cohort: Opportunities, Successes, and Challenges," see ED562061. For the third paper in this series, "Building Blocks for Better Schools: How the Next Mayor Can Prepare New York's Students for College and Careers," see ED562069. For the "Initiative Overview & Summary of Research," see ED562084.]