Soon after reading Chogyam Trungpa Rinpoche’s Meditation in Action in the early 1970s, Gaylon began attending summer seminars with Rinpoche in Vermont. In 1973, Gaylon joined Tail of the Tiger Buddhist Community (now Karme Choling) where he worked in the garden and took people into retreat. After attending the three-month 1975 Vajradhatu Seminary, Gaylon taught at the Naropa Institute. He later served as Executive Co-director of Karme Choling. From 1979 to 1986, Gaylon held several teaching and leadership positions within the Shambhala community, including at Berkeley Dharmadhatu and the Office of Three Yana Studies in Boulder.
Gaylon enrolled at Yale University (for a second time) in 1987 to finish his undergraduate degree in African Studies. In 1994, he was a Fulbright Fellow to Nigeria and completed a doctoral degree in cultural anthropology at Stanford University two years later. After several years teaching cultural anthropology at the University of Washington, Gaylon moved to Karme Choling as teacher in residence through 2005. In 2006, he was Visiting Professor in Religious Studies at Naropa University. He went on to teach Interdisciplinary Studies at Naropa University for 15 years, and has written three books: Natural Wakefulness (on the four foundations of mindfulness), Natural Bravery (on fear and fearlessness as path to enlightened society), and Welcoming Beginner's Mind (on Zen and tantra). His article, “Making Friends with Ourselves” (from the pioneering collection Dharma, Color, and Culture) was selected for inclusion in The Best Buddhist Writing: 2005. He wrote the foreword to Black and Buddhist: What Buddhism Can Teach Us about Race, Resilience, Transformation and Freedom. Gaylon recently relocated to the Hudson Valley of New York where he lives with his partner and several cats.