We report on a qualitative study about the presence and role of insider knowledge in the lives of talented adolescents. Several themes emerged from the interviews: career aspirations of the participants; sources of knowledge about colleges and choosing a college; sources of knowledge about STEM careers; anticipated challenges; required skill sets; and types of support needed to address challenges. Participants received college guidance from school counselors and used the Internet as a primary source for STEM-related activities and information. Participants formed their ideas on what life is like for a STEM professional based on people they knew, TV shows, and social media, with more realistic notions acquired by students with a family member in STEM. Commonly experienced and anticipated challenges were competition in school and in college admissions. Time management was identified as a necessary skill, and the most frequently cited support needed was guidance with respect to career paths.