Since its inception in 2011, Museum Teen Summit (MTS), a youth-led collective dedicated to better understanding and transforming the role of young people within museums, sought to act as a bridge between teens and cultural organizations. Over eight years, MTS built an impressive network of youth and adult professionals interested in specialized programming for teens in museums, conducted research on teen agency in museums, organized events for teens within museums, and presented at professional conferences across the country. The work of the over ninety young people who cycled through the collective was a resounding success, but with notable flaws and space for improvement. A closer analysis of the work of MTS also reveals less conventionally recognized successes. This collectively written article, authored by youth alumni and an adult collaborator, analyzes definitions of success and failure in youth-led organizing and research and how they shaped our work and our experiences.