How Billy Planer Turned Cross-Country Teen Journeys Into Lessons for Conversations That Matter
By: Brenda Myles
Long before Billy Planer began writing Conversations That Matter, he was putting its central idea into practice on buses, in meeting rooms, at historic sites, and across communities throughout the United States. His work has taken more than 35,000 people on educational journeys built around listening, identity, public issues, and firsthand encounters. The best-known early example was Etgar 36, the five-week summer program he created in 2003 to help teenagers examine what they believed by meeting people who strongly disagreed with one another.
The concept grew out of Planer’s experience leading youth groups. He had already been taking teens on annual weekend trips to different cities to explore local history, culture, and civic issues. He wanted participants to understand how those places and stories related to their own identities as Americans. Eventually, he expanded the idea into a national journey focused on history, politics, and activism.
Rather than presenting one approved viewpoint, Etgar 36 placed opposing perspectives in front of participants. Planer describes the purpose as giving teens the opportunity to discover what they thought by engaging in civil discourse with people they disagreed with. In one sequence, the group met with a father whose son was murdered at Columbine High School in 1999 and who became a national activist for gun safety. Two days later, the same teenagers met with a gun-rights lobbyist and activist. The structure required them to listen across a divide rather than learn an issue from a single source.
Planer used similar encounters on abortion, marriage equality, climate change, marijuana legalization, and wealth disparity. The point was not to make every participant reach the same conclusion. It was to make sure their conclusions had been tested by contact with arguments, experiences, and people they might otherwise never encounter. That method became one of the foundations of Conversations That Matter.
Planer summarizes the book this way: “Conversations That Matter is about how and why we must talk with people who don’t look, think, pray, love, and in 2026, vote like us.” He adds, “We must become comfortable being uncomfortable, having what I term a conversation that matters.” For readers who have seen political or cultural disagreement end relationships, the phrase is an invitation to stay in the room longer and learn how to manage discomfort rather than treating discomfort as a signal to leave.
His approach also asks people to examine the strength of their own beliefs. Planer compares disagreement to a test drive. “All we are doing when we speak to someone who we disagree with is we are test driving our thoughts, beliefs, and opinions,” he says. “You would never buy a car without test driving it and seeing how it handles curves, potholes, etc. Why would you hold on to core beliefs without seeing how they stand up to any pushback? If you can’t defend your views, how strong are they really?”
The work eventually expanded well beyond the original teen journey. In 2004, Planer began leading three-day Civil Rights journeys in the American South for both adult and teen groups. He says those experiences reinforced his belief that leaving familiar surroundings can make people more open to ideas and encounters they might normally avoid. A new setting can interrupt routine, lower defenses, and make it easier to ask questions that might feel too risky in an ordinary social environment. That insight now appears in the book as a broader invitation to stretch conversational boundaries.
That does not mean Planer expects disagreement to become pleasant. He says difficult conversations may never feel comfortable. The more realistic goal is to become more capable inside them. The techniques in his book are intended to help readers remain calm and confident, reduce the chances that a discussion becomes overheated, and avoid taking every challenge as a personal attack.
The same philosophy explains why Planer values travel as a teaching tool. New places disrupt routine. They expose participants to histories, communities, and perspectives outside their ordinary environment. In Planer’s view, that physical movement can mirror the intellectual movement required by a serious conversation: leaving what is familiar, crossing into discomfort, and returning with a broader understanding.
More than two decades after Etgar 36 began, Conversations That Matter translates those experiences for readers who may never board one of Planer’s buses. Its lessons come from thousands of face-to-face encounters and a belief that disagreement can sharpen ideas without destroying relationships. The book asks readers to approach conversation not as a contest to win, but as a chance to understand what they believe, why they believe it, and who is standing across from them.
Conversations That Matter is available on Amazon.
