The contemporary education system in the United States is inadequate in the provision of services to assure that all students exit high school with the knowledge and skills necessary to enter postsecondary education or the workforce. This is particularly true for indigenous youth (Tanabe & Mobley, 2011). According to scholars, dual enrollment appears to be an appropriate solution for assisting indigenous youth to perform better in high school and to be better prepared to enter postsecondary education and the workforce (Rodriguez, Hughes, & Belfield, 2012; Vargas, Roach, & David, 2014). As demonstrated in this study, promoting dual enrollment programs, for Native Hawaiian youth, along with mentorship and financial assistance, has a positive impact on post high school outcomes. Thus, after describing the goals and model of Project Ho'oku'i, this article reports on the experiences and perceptions of Native Hawaiian youth who participated in a dual enrollment program (i.e., enrolled in high school and postsecondary education simultaneously). This study utilized grounded theory methodology. Focus groups, with semi-structured open-ended questions, were conducted with 103 participants over a 24-month period. The findings of the research comprise two major themes that are concerned with Native Hawaiian students' educational "Progress" at large and address the issue of "relationality," including the practice of self-sufficiency in sorting through future career options and learning one's sense of self-in-society, in particular its relational aspects.