For a number of years enrollment at St. John’s High School on John’s Island has been declining. Students are being lured away by magnet and charter schools and other opportunities, leaving the school at a disadvantage with lower student numbers and funding. In an effort to create opportunities for the current student body and to better compete for potential student enrollment, St. John’s High School embarked on a strategic planning process. To that end, a strategic plan was established with several goals. One goal is to create internship opportunities for St. John’s High School students to provide them with exposure to various career options on and off the island. In an effort to assist with this strategic goal, this DLI cohort is supporting the high school in this initiative by creating internship opportunities, assisting with collateral materials to bring to potential internship locations, working with students for internship readiness and by exploring funding streams for stipends and transportation.