A Long Lesson in Storytelling, Which Includes a Story

The first books I wrote were 800-page monstrosities. When I was given my first recurring 800-word magazine column, my editor said something wonderful: “It’ll make you a better writer.” He was correct, and that was never demonstrated better than at a bar I went to last month.

The bar itself wasn’t new, but we’d not made it in yet, and we’d been wanting to. So we chose a Wednesday evening to pop in. When we got there, the place was packed… with people wearing suits, which is not a usual Vegas thing, especially with rodeo in town (which it was).

Turns out there was a whiskey brand that was doing a launch in our market, and so the local distributor had set up a shindig at this bar. Bemused, we ordered drinks – made with the new whiskey, which was excellent – and sat down to enjoy.

Within moments, the owners of the distillery were up on stage, telling us they wanted to “share their story” of how the whiskey came to be. I love a good story, and I especially love stories with whiskey in them!

Sadly, that was not to be. Here’s where storytelling goes wrong, and why it’s often good to constrain yourself, either space-wise or time-wise, to keep yourself from going off the rails.

Our story started with September 11th, 2001. Yeah. And if I’m being honest about my selfishness, that’s not really the kind of story I was looking for that evening. My intent had been to relax, have a cocktail, and enjoy the evening before dinner; I’ve no problem with history lessons, but I kinda need to be in the right frame of mind. Especially when it’s such a somber history lesson.

The story lesson continued, and it turns out that the three owners of the distillery had been Green Berets during 9/11. They had, in fact, been conducting an anti-terrorism exercise right when 9/11 happened, and so as they were getting the initial news they thought it was part of the exercise. It took them some time to realize this was happening, and it wasn’t long thereafter that they were deployed to Afghanistan on a kind of follow-up mission.

Their story was rich with detail. They had a map of Afghanistan. They named the warlord that the US was trying to partner with, and outlined his sketchy history at keeping his promises. They described being heli-lifted into the theater, over the freaking tallest mountain range on Earth, and talked about the tough decisions you have to make when you’re flying in that weather, at that altitude, in a very weight-sensitive aircraft. Decisions like not taking a flak vest. Or a helmet. Because you needed to save the weight for the ammo.

Now, we’re ~10m into the story at this point and there has been no mention of whiskey. Everyone in the room is torn: we’re all obviously in awe of what these men, and their compatriots, have done for our country. We’re in awe that these things can even be done at all, and we’ve got the people who did them standing just feet away from us on a stage. We want to be respectful of their service, their sacrifice, their risk, and their contributions.


We also wanted the whiskey. We were kinda promised the whiskey.

The story continues: they met up with some of the locals who were going to participate in whatever the mission was (I will admit that, despite my fear of there being a pop quiz afterwards, I was starting to lose some of the fine details of the story, because there were so many details). The locals were on horseback, and despite the fact that most of the Green Berets had never ridden a horse, they saddled up.

I am conflicted, but for the sake of truthfulness I must admit that this is where we left the bar.

The whiskey, Horse Soldier®, has a more succinct story on their website:

Days after 9/11, the USA responded with a daring insertion of small teams of Green Berets, mounted on horseback, into Northern Afghanistan. These brave men are honored today by America’s Response Monument at Ground Zero in New York City. Nicknamed the “Horse Soldiers”, these same men make the bottle in your hand emblazoned with the image of this statue. Horse Soldier® Bourbon is award winning and authentically made with all-American ingredients. The Horse Soldier® glass bottle is molded by steel recovered from the World Trade Center to commemorate the lives lost and never forgotten.

So, that’s an excellent story. Actually, telling me that story – in that succinct way – has caused me to tumble down the Wikipedia rabbit hole, reading about the America’s Response Monument, about these “Horse Soldiers,” and more. But in the bar, at the time, I was confused. I didn’t know where it was all going, and I was having trouble connecting the 10m mission briefing to whiskey – and I’d been promised a whiskey story.

So what are some lessons here?

Well, there’s really only one: when you set out to tell a story, or explain something (which is a form of storytelling), ask yourself one question:

What am I promising my audience the outcome will be?

It doesn’t matter what story you want to tell. What matters is, what have I promised – explicitly or implicitly – my audience will get out of this?

And once you know that, you take the shortest path to that outcome.

Every been long-hauled by a taxi? Everyone hates that. I told you to get me to Point B, and you’re expected to take the shortest/quickest way there. Same with storytelling: don’t long-haul your listeners! Make it clear where you’re taking them, and then get them there as quickly as possible. Sure, you can drop teasers about the tangents in your story, because tangents can be interesting. But you don’t hijack the listener and force them onto those tangents. Stick with the mission.

So as you construct a narrative, ask yourself: what of this could I drop? What of this does not contribute to the outcome I’m advertising? How can I make this story even shorter? What details are irrelevant?

I have a friend who often sweats details in his stories. “So the other night – no, was it Monday? No, it was Tuesday, wasn’t it, because we’d just watched that TV show and it just came out Tuesday. So yeah, Tuesday, we were talking to George. No, it wasn’t George, what was his name? The guy with the –”


If the detail doesn’t directly lead to the outcome, then skip it. Those gentlemen’s story of their whiskey did not need to include the exact type of weapons they carried or the kind of ammo they put into it, but we were treated to that detail regardless. And I get it: that detail interests them. In a peer group, that detail would be appreciated, and they’d likely be questioned about it if they excluded it. But it didn’t contribute to the outcome, and so it wound up being cruft that we all had to wade through in an attempt to get to our destination.

There’s an art to storytelling, and a big part of that art is recognizing that the listener determines the value of the story. Not the teller. You can’t tell the story you want to tell; you need to tell the story that your audience wants to hear. You can guide what they want to hear by setting up a clear expectation in advance, but once an expectation exists, the best storytellers deliver that expectation in as concise a way as possible.

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