There is value in strengthening the transition from high school to college and careers for all students in the state of Indiana. Local school districts, Indiana University Kokomo partners, and regional agencies worked together on the Department of Education “Explore, Engage, and Experience” (3E) Grant to enhance career exploration and pathway engagement for P-12 students in north central Indiana. This work was informed by the “grow your own” approach, which leverages both college and high school capacity and staffing to create new opportunities for high school students through dual enrollment or dual credit courses, intentional college advising, career development and professional networking, and work-based learning. We share our process of planning and implementing the program. Our goals of increasing career exploration engagement, work-based learning, and credentialing activities were met. We evaluate the outcomes, sustainability, and future practices or considerations for these kinds of programs.