School librarianship is affected by the widespread challenges affecting schools and changing notions of school libraries' relevancy. The purpose of this study was to ascertain how these societal trends influenced educators' decisions to be school librarians. In this second phase of a longitudinal qualitative study, five school library program graduates were re-engaged four years after the conclusion of the first phase. Critical event narrative analyses of interview transcripts suggested that while their preservice education experiences prepared them to embrace school library and technology leadership, some participants chose not to pursue or stay in school librarianship and applied their preparation to roles as classroom teachers and school administrators. Many participants' choices reflected themes found in literature pertaining to situated learning, transfer of training, transfer of skills, and leadership development. In addition, the powerful presence of teacher acculturation factors and phases of career development affected the experiences of these school library preparation program graduates.