How can teachers help prepare their high school students to make the critical transition to what comes after they graduate? Teachers cannot wait until students are seniors to inspire them to consider postsecondary education or training, and at the same time prepare them to succeed when they get there. It is increasingly important for students to continue their education beyond high school, not only for their future--both opportunities and earnings--but also for their country's future. In many cases, high school graduates may not be prepared for college or the workforce, even if they have passed the required mathematics courses and exit tests for graduation. The worlds of high school and postsecondary education, especially with regard to mathematics, may seem light-years apart. This article discusses the steps taken by high school teachers and higher education faculty to bridge this gap in mathematics and to ease their students' transition.