Not too long ago I attended an online retreat with Joseph Goldstein, cofounder and guiding teacher at the Insight Meditation Society in Barre, Massachusetts. I've sat with Joseph on retreats before, but what really struck me this time were the repetitive patterns playing out in my mind and body, whether it was getting lost in stories and caught up in self-judgment, or simply being distracted by physical pain—all pretty common experiences on a meditation retreat. In today’s episode, I sit down with Joseph, who recently emerged from a 3-month silent retreat himself, to ask him some questions that have been at the top of my mind. We’ll talk about the value and challenges of a long retreat, the wisdom of investigation and curiosity, and why we need to make more room for joy and humor on retreat and off. At the end of our conversation, Joseph will lead us in a brief mindfulness meditation to re-ground ourselves in the present moment. —James Shaheen, editor-in-chief of Tricycle: The Buddhist Review.