In this essay, a high school senior reflects on her educational experience as a journey beginning with her difficult decision to stay at Francis W. Parker School for high school and ending with her current search for a college where she can continue to explore the nature of education. Her narrative focuses on her experience in an elective course called Schools Across Borders, Schools Across Time, a project course designed to produce a documentary video for an international conference on the intersection of two educational heritages: soka education in Japan and progressive education in the United States. She delves into reflections that took place within the course, including a visit from a Japanese delegation, the study of other progressive schools, an all-school assembly presentation, and the school's showing of Race to Nowhere and ensuing discussion. After the course ended, the author proposed an independent study on education for her junior year. Her study of John Dewey's Democracy and Education confirmed her commitment to schooling as a social rather than an individual enterprise. Her study of Paulo Freire's Pedagogy of Freedom affirmed the value of education as the discovery of agency. Much as she venerates the social values of cooperation and shared learning, it is still difficult for her to balance her intellectual commitment with the very real demands of the next stage of her education. Since college admissions largely isolate and reward the individual in competition with others, the author continues to wonder about how to reconcile her values with her ambitions. (Contains 1 figure.)