High school students often find the college application process daunting and stressful. One area of concern is the application essay. This study examines the feelings of students who recently completed writing college application essays and videos. This study explores the experiences of students at a diverse high school near Atlanta, Georgia, during and after the process of creating college application essays and videos. The experiences of students during the application process were important to study because (1) there was a gap in the knowledge base related to the evolving role of essays and videos in the college application process, and (2) acquiring a better understanding of student experiences will augur ways to both diminish the stress of the process and encourage teachers to better assist students during the process in the future. The work of nine participants was analyzed, and then participants provided feedback about their experiences during the process of creating the work. The study found that the iterative process of working on meaningful essays and videos often has a powerful effect on students, helping them to better understand the meaning of their life experiences.