The Freedom Writers Diary is organized as a set of diary entries, alternating a few that Erin Gruwell wrote with a large number that various students in her class wrote. In entry 1 by Gruwell, dated fall 1994, she writes about her upcoming first day of teaching as a regular teacher and remembers her experiences the year before as a student teacher. Her unconventional teaching methods had irritated the principal, so she was assigned to teach a class of under-performing students.

Gruwell wonders what these students will think of her. Her thoughts regarding their possible opinions range from her style (“too preppy) to her age (“too young to be taken seriously”) and include her ability to relate to their experiences (“too out of touch”). She contemplates asking them to write journal entries that relate to their expectations, both of the class and of her. This implies that she has already decided to use the journal-keeping method.