How to Tell a Great Travel Story: Q&A with Esther Choy

Have you ever tried to tell the story of something exciting or funny that happened on vacation, but you fell flat? Don’t feel bad, says storytelling coach Esther Choy, the founder and president of the Leadership Story Lab in Chicago. It happens to all of us.

Taking a break during a family ski vacation in Park City, Utah, Choy coached us on how to be a better storyteller when sharing our own travel tales.

Independent Traveler: In general, do you think most people are good or bad at storytelling?

Esther Choy: Most people have wonderful stories buried in them. But there are a few things they can do to tell them better. What makes a novel a page-turner is that at every critical juncture of a plot, readers find out a bit more about the characters, and yet there is another cliffhanger. So the novel is intriguing their audiences.

You don’t need to handcuff yourself to recounting events as they unfolded per their chronological order. Telling stories involves an intriguing beginning, a riveting middle and a satisfying end. This three-act formula can generate an hour-plus-long story, or it can be a 30-second experience.

And you don’t have to be a superhero to tell great stories. Sure, if you’ve just climbed Kilimanjaro while hoisting your aging parents and barely walking toddler twins along, you’re a superhero. But a compelling tale can be as seemingly mundane as getting through a quarter of your reading list during a laid-back beach vacation. A great story relates the central theme of your story to a universality, a shared human experience.

IT: What other components make up a good travel tale?

EC: You have to balance indulgences with an experience your listeners can relate to. Of course, if you’ve discovered the best ramen in the world, by all means, share that. But if your tale is mostly about touting one indulgence after another, then you’re creating a “Facebook updates” experience for your audience. Yawn!

A good travel tale has a well-balanced mix of new, pleasurable discovery and universal experience. Let’s say that after discovering your favorite ramen restaurant in Honolulu, you went overboard and ate ramen every day for five days. Then you had indigestion and didn’t love the ramen place as much. As you wrapped up your tale, you reflected on how even a little bit of self-restraint could have perfected the whole experience. In this story, discovering the best ramen is the indulgence. Exercising more self-discipline in order to preserve a wonderful experience is the universality.

IT: Before you start telling a story, what should you think through to make sure the story is well received?

EC: Always keep your audience’s preference in mind. With an adventure story, some might be more intrigued by how you arrived at the best whitewater rafting part of the Grand Canyon. Some might wonder how you justified to your boss that taking a month off for this experience would make you a better employee.

No matter the preference, treat the storytelling more like a dialogue, implanting hooks for questions, rather than doling out one long monologue. In my upcoming book Let the Story Do the Work, I talk about how “aggressive listening” is a prerequisite for good storytelling. The main idea is that you want to incorporate what is important to your audience as you’re telling your stories.

IT: What should you do if you notice that your listener is losing interest?

EC: It’s important to pay attention to signs of waning interest. They’re smiling too long. They’ve stopped mirroring your body language. They’re looking toward the door or at their phones.

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Cliffhangers help. And if you’re telling a travel story in an informal setting, know that your story doesn’t have to be a monologue. Take advantage of natural back-and-forth of dialogue to break things up. Ask a rhetorical question — “Guess what happened next?” And use humor to re-engage interest.

IT: Does it help to show visuals, such as photographs or souvenirs?

EC: Visuals can help, but be highly selective. A picture can speak a thousand words, but only if you’ve chosen a good one. For example, my husband and his friend are very advanced skiers. One day, they ventured to the peak of Red Pine Bowl in Park City. Once they summited, they saw a sign that said “You are leaving the ski resort. You can die.”

As they shared their stories over dinner, all they said in the beginning was, “We HAVE to show you this sign.” And they refused to say anything else. This was highly effective because it left us wondering, what was that sign? Why wouldn’t they say anything else?

IT: Okay, you got us. What happened next?

EC: On a ski lift, my husband Bernhard and his friend Nik met a local skier who recommended that they hike up to the top because the view was worth it. It was already toward the end of their day and they were tired. But then they thought, what the heck? Just as they reached the top, though, they saw the sign.

At this point during our dinner, Bernhard and Nik paused. With a smirk, Bernhard said, “This sign got me thinking…” And then his voice trailed off. Nik chimed in, “I wondered what would happen if…” His voice trailed off too.

I have witnessed Nik promised his wife not to do any double black hills with a cliff or anything “too risky” on several occasions. His wife and I looked at each other, and waited for more in full anticipation.

“So we took a left, followed the trail and went back down.” And that was that!

As you can see, in this little story no one got hurt and no one died. No one even attempted any highly risky act. The only highlight was the sign. Although the sign was a bit dramatic in its messaging, there wasn’t any other dramatic element in the whole story. But Bernhard and Nik know their wives well. They made full use of anticipation, pauses and dialoguing to tell this fun tale.

And by the way, the view was so worth it.

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What’s your favorite travel story?