In response to the 2000 Virginia state writing prompt, eighth grade students wrote a letter of advice to a sixth grader coming to middle school for the first time. A purposeful sample of more than 10,000 writing responses was collected. Content analysis of a random sample of 350 responses revealed themes of advice for students negotiating the transition to middle school. Content analysis revealed that organizational themes were mentioned more frequently than personal/social or academic themes. The most frequently mentioned themes in each category were choosing and changing classes or electives, improving study habits, and making and managing friends. Data also revealed wide diversity in advice and a robust sense of student agency, including recommendations of student attitudes and attributes that were deemed important for new middle school students. Implications for middle school personnel are discussed and future research directions are presented. (Contains 1 table.)