A committee comprised of the former state superintendent and educational leaders launched a unique high school program (pseudonym Connections) to support the delivery of a high school curriculum that would prepare students for college and careers. Students in Connections complete their 4 years of high school, supported by an Advocate who guides them in developing a personal plan to help them select courses and experiences. It was implemented in 2016 in one of 10 comprehensive high schools in a mid-Atlantic public school district. This phenomenological study explored 16 of these graduates' lived experiences. The research was conducted to help other researchers and those interested in evaluating what graduates find compelling in assisting them in preparing for college or the workforce. Participants were interviewed using a semi-structured protocol. Additionally, four key staff members and three business partners were interviewed. These supplemental interviews, as well as a researcher journal used to mitigate bias, provided data triangulation. Using Social Cognitive Theory as the Theoretical Framework and Positive Youth Development as the Conceptual Framework was used to analyze for a deeper understanding. The research addressed the participants' perceived value of various program aspects. Five themes were present in the graduate's experiences: (1) appreciation of college and business visits, (2) increased feeling of being well-prepared, (3) appreciation of dual enrollment, (4) appreciation of exploring career and college options, and ultimately, (5) elimination or reduction of stress. Sub-themes were also identified. Findings reinforce the value of having a formal Advocate position and business and college visits by students. Implications and recommendations for policymakers include providing additional funding for Advocates, improving how students receive credit for classes through demonstrating mastery, making it easier for employers to offer experiential opportunities, and providing more transportation. Future studies should consider including parents. They should also include graduates who attended all 4 years in person, who had adverse outcomes after they had completed college or 4 years in the workforce, and who are more representative of the school's population. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]