The Courage to Keep Listening
There is a particular loneliness in being certain that no one is listening. We can fill our days with words, publish our convictions, gather affirmations, and still feel that we have reached no one beyond those who already agree. Meanwhile, the distance between us grows.
My friend Billy Planer has spent decades walking into that distance. His book, "Conversations That Matter," invites us to join him.
Drawing on his work leading Etgar 36 journeys through American history and contemporary life, Billy introduces us to people whose stories complicate the categories we carry. His educational method asks participants to encounter human beings, listen to how their convictions developed, and notice what happens within themselves when someone refuses to fit a familiar outline.
That matters so very much. We often imagine listening as something we offer another person. Billy reminds us how much it requires of the listener. Can I recognize the moment when curiosity gives way to preparing my rebuttal? Can I ask a question whose answer I have not already decided? Can I tolerate the discomfort of discovering that someone I disagree with has something to teach me?
These are deeply spiritual questions. They concern the habits through which we become human together.
As a rabbi, I hear in Billy’s work an echo of the Jewish insistence that every person bears God's Image. That teaching becomes demanding precisely when someone’s words anger us. Recognizing another person’s humanity can require tremendous discipline when the stakes of a disagreement are real and our own wounds are close to the surface.
I also appreciate that Billy makes room for boundaries. Conversation requires willingness. Safety matters. Sometimes stepping away is wise. The invitation to listen carries weight because it leaves room for judgment about when an encounter is possible.
His practical guidance gives that invitation substance: speak from your own experience, ask sincere questions, pay attention to your posture and tone, allow mistakes, and release the need to win. Anyone who has attempted these things during a painful disagreement knows how much practice they require. Even taking a breath before answering can become an act of moral courage.
I found myself especially moved by the role of story in his approach. An argument can become abstract very quickly. A story asks us to picture a life. It gives a belief a history, a geography, a family, a wound. We may remain unconvinced. Yet we have encountered someone whose existence exceeds the position we oppose.
For those of us committed to public leadership, this is a necessary challenge. Our words shape the rooms others must inhabit. We bear responsibility for what we defend, how we speak, and whether people leave our presence more capable of encountering one another. Passion and humility belong together. So do conviction and curiosity.
Billy’s book leaves me thinking about the world we build through ordinary exchanges: the question asked without a trap inside it, the moment of restraint, the unexpected admission, the willingness to remain present. These gestures can prepare people for the sustained work that change demands.
On December 6, I will have the pleasure of joining Billy for a public conversation in Westchester about Conversations That Matter. I am grateful to call him my friend and eager to explore these questions together. You can find event information at https://billyplaner.com/events/. You can purchase your own copy of the book here: https://a.co/d/0cLbC37Z
I hope you will join us. Billy has given us a generous invitation to practice something our communities urgently need: the courage to listen closely enough that another person becomes more fully visible. We can begin with the next conversation, carrying our convictions, making room for surprise, and remembering that the person before us has a story.