The article documents the process by which four independent high school students from the Francis W. Parker School in Chicago and the faculty adviser of their school newspaper, "The Weekly" (a monthly), produced a daylong journalism symposium designed to promote and explore democratic education, student leadership, and professional mentorship in high school journalism. The five authors individually and collaboratively reflect on how the experience of bringing together 10 professional journalists, one professor of journalism, and students from six schools around Chicago created a forum for discussion of the rapidly changing field of journalism and helped articulate the complexity--and the potential for productive interaction--of one city's journalism community.