As of 2015, 42 states reported some type of entrepreneurship education standards, guidelines, or proficiencies and 18 states required entrepreneurship education courses to be offered at the high school level. Yet, there is limited qualitative literature on students' experiences in degree-granting entrepreneurship education secondary school programs that promote an entrepreneurial mindset. This leads to a limited understanding for secondary school leaders and curricula developers designing and implementing these programs, which potentially results in the design and implementation of ineffective programs. The purpose of this qualitative, phenomenological study was to explore high school students' lived experiences earning a high school Entrepreneurship Diploma (ED) that was designed to promote an entrepreneurial mindset. This study collected and analyzed qualitative data from ED Cohort 1 members, their parents, and former program faculty, primarily through questionnaires, interviews, and reflection matrices. Four results emerged from the study's findings: (a) Uncertain and Non-Traditional Future Work Landscape Necessitates Diverse and Holistic Skillset, which the ED Promoted; (b) Participation in Numerous and Reoccurring Experiences that Enable High School Students to Apply Classroom Learning to Real World Problem-Solving and Presentation Empowers Students to Develop Confidence and Take Risks; (c) Sustained Collaborative and Teamwork-Based Learning Leverages Social Relationships and Helps Students Develop and Understand the Value of Support Networks; and (d) Self-Reflection and Feedback in the Context of Entrepreneurial Mindset Development Enable Powerful and Purposeful Self-Discovery of Authentic Identity. These results are valuable to secondary school leaders and curricula developers designing and implementing entrepreneurship education programs that promote an entrepreneurial mindset in students. Since these results also indicate the skills with which high school students might be entering college or the workforce, these results are indirectly valuable to college administrators and employers, who desire entrepreneurially minded individuals or employees.