When Winning Backfires…

There is something magical about a great dinner party. Good friends and food bring people to the table, but it’s the conversation that keeps them there.

Artists and treps get passionate and pumped for events like this—it’s in our nature. And the conversations can sometimes become animated, dramatic, and loud. That’s great—until the conversation shifts from exchanging ideas to winning arguments. The moment that happens, the goal is no longer to learn, understand, or resolve an issue. The goal becomes proving I’m right.

I’ve noticed that when people start talking in “is’s”—“This is the future” or “This is how it’s going to be”—people stop listening. Some tune out, while others quietly walk away from the table. And when that happens, many of today’s most important debates—especially around AI, politics, and money—stop short of making any real impact.

Certainty tends to close doors that curiosity leaves open.

AI is a perfect example. Tell a room full of artists and treps that AI is going to replace actors, musicians, writers, and visual artists, eventually turning the entertainment industry into a world of algorithms and robots, and you’ll have everyone’s attention.

But that’s only half the story. AI can also act as a collaborator, assistant, researcher, sounding board, editor, and idea generator—even when we remain the creators. It can help level the playing field by opening doors to opportunities that many of us can’t yet see. While AI may disrupt some creative jobs, it is also likely to create new roles and new ways for artists and treps to apply their talents, while providing access to opportunities that once required the approval of traditional gatekeepers.

However, some people feel compelled to keep sounding the doomsday alarm, assuming others haven’t heard it. But the truth is, the dark side of AI has dominated headlines, podcasts, social media, and dinner-table conversations for years. Most people have already heard the warnings, even though the story is still being written.

That said, while the drama grabs the headlines, the upside barely gets a footnote.

Important because the best conversations in the deep end of the pool often happen where certainty ends and curiosity begins—especially when none of us has all the answers. Because the goal isn’t to win the conversation. The goal is to elevate it.