Kellee E. Warren is Associate Professor and Special Collections Librarian for University of Illinois Chicago, where her current research is on teaching with Chicago design collections and Black representation in nineteenth century children’s literature in the U.S.. In this presentation, she will facilitate a candid discussion on the benefits and challenges of advancement into management and leadership for both early and mid-career librarians. While some early career librarians have the curiosity and ambition to become part of senior management, even with library manager training programs, they are often not set up for success. Concurrently, through personal experience, observation, and an intuitive sense of the sacrifices, many mid-career librarians often find themselves in middle management roles and are reluctant to advance to senior management. This presentation will provide a brief history of U.S. management practice, discuss the importance of specific skills and training, and interrogate what it means to be a library manager and/or leader.