What I Learned about Storytelling Through My Years in the Tour Business

Storytelling often feels like a natural gift—something that some people are born with and others are not. But in reality, it is as much a skill as it is a knack, and like any skill, it can be learned, practiced, and refined. Storytelling is not the same thing as memorization. Anyone can commit dates and names to memory, but that alone does not create a compelling narrative.

In my business—Custom Tours of DC—being able to tell a good story matters more than sharing factoids. Tour guides carry the outlines of the stories in their head, holding onto the structure while allowing space for flexibility. With each retelling, the stories can be reshaped slightly: details emphasized or downplayed, examples swapped, and pauses inserted at just the right moments. It is a dynamic, living art, one that depends not only on the material like the theme of the overall tour, but also on the audience’s reactions in the moment.

This is one of the things that makes storytelling so powerful: the same story can sound different depending on who is listening and where it is being told. A group of children may need playfulness, vivid imagery, and quick pacing to stay engaged, while a group of adults might prefer deeper reflection, wit, or connections to current events. The setting also matters. A story told during a walking tour in the bright light of day carries a different rhythm and tone than one shared at night, when the air feels heavier and the monuments are glowing in the dark. Even the mode of travel changes the delivery. A story told on a bus may rely more on voice and timing, while a walking tour invites gesture, pauses, and a sense of place. In the world of tours, there is also the element of improvisation. A single question from a participant can shift the energy, sending the guide in a new direction. The best storytellers embrace this, weaving spontaneous threads into the fabric of the narrative.

For me, the heart of storytelling lies less in the facts themselves and more in the connection forged between storyteller and audience. I don’t care how many facts someone can rattle off. If those facts land cold, without meaning, they have no impact, they don’t endure. What matters is whether the storyteller can make people feel something—curiosity, amusement, awe, or empathy. Authenticity is the key. A story becomes powerful when it reflects the storyteller’s own voice and perspective, shaped by their background, their passions, and their experiences. Two guides can tell the same historical account, but each should put their own stamp on it. That is what makes the telling fresh, what allows it to resonate.

When I hire tour guides, this quality is what I listen for above all else. Facts can be studied, routes can be learned, and logistics can be rehearsed. But the ability to connect with an audience—whether a family of five on vacation, a classroom of teenagers, or a group of executives on a company retreat—cannot be faked. It requires a blend of empathy, confidence, and presence. The best guides are those who care about the impact their stories have on participants. They want people to walk away not only with more knowledge but also with a memory that lingers long after the details fade.

At its core, storytelling is about making history come alive. It bridges the gap between past and present, fact and feeling, information and imagination. A good story does more than explain what happened; it helps us understand why it matters. That is why I believe storytelling is not only an art but also one of the most important tools we have for making meaning—whether on a tour of Washington, D.C., around a family dinner table, or in any setting where human connection is at the center.