Professionals who work with youth can have a tremendous impact on the development and life trajectory of these young people. This article reports on an effort to provide support and professional development for those who work with youth during nonschool hours in a youth development fellowship program. Combining intensive residency workshops and a six-month coaching experience, the fellowship was designed to teach participants how to integrate youth resilience and youth development perspectives into their work. The evaluation collected data from the fellows and their coaches during the course of the program. The study offers insights into the types of benefits achieved through this type of focused intervention with youth workers, as well as the challenges of conducting such an effort.