Frederico Trancoso, born and raised in Brazil, has spent many years engaged in contemplative practice within the Düdjom Tersar Tradition of Tibetan Buddhism. As a result, he now serves as the retreat guide at Pema Ösel Ling, a center located in the hills above Santa Cruz, California. In our in-depth discussion, he explores the relationship between written and oral traditions in guiding contemplative practices. He shares insights into when written material serves as a support and how oral guidance, as an essential part of transmission, reveals key aspects of personal understanding. Additionally, Frederico Trancoso provides a comprehensive overview of how a three-year retreat in his tradition is structured, as well as the challenges participants face.