The road from prekindergarten (pre-K) to post-doctoral (post-doc) work is riddled with potholes, detours, u-turns, and construction zones. National education initiatives such as No Child Left Behind, the Common Core, Race to the Top, Performance-Based Funding, College Readiness and Completion Acts, and Post-Graduate Gainful Employment Reports demonstrate attempts by government agencies to increase high school and college completion rates in the United States. Currently, students and their families who investigate the options for higher education lack a clear map to guide them. Today's students are told that college is either the best investment they can make or a waste of time. As a result of government involvement as well as student and family expectations, education administrators are under increasing pressure to ensure that all students succeed from pre-K through "grade" sixteen. To ensure a smooth transition from secondary to postsecondary education, administrators from both groups must come together to build roads of transition for all. The purpose of this article is to identify the road blocks that currently exist and to recommend patches that can be put in place in building roadways for students' smooth transition from pre-K through grade 16.