The Indiana Library Leadership Academy (InLLA) was established in 2012 by the Professional Development Committee of the Indiana State Library (ISL). Modeled after the American Library Association (ALA) Emerging Leaders program, the InLLA brings together librarians accepted into the program from public, school, academic, and special libraries throughout Indiana. A new cohort of librarians is invited each year to a week-long workshop in July, where participants are divided into teams to work on a year-long capstone project and facilitate InLLA group meetings via webinar. This paper chronicles experiences of four academic librarians from the 2013 cohort of the InLLA. It will highlight four different capstone projects for which each of the academic librarians contributed, respectively, with their fellow group members. This paper will identify the greatest challenges each respective group faced during their year-long collaboration, as well as the learning experiences of each author’s participation in InLLA.