How To Become An Awesome Storyteller

June 19, 2013 | No Comments » | Topics: How To

by Marcus Geduld

Just as with any skill, practice, practice, practice. Unfortunately, that means telling stories now, while you’re still bad at it. Getting good at anything means trying, failing, learning from failure, and trying again. Go ahead and fail, but keep a journal of your failures, analyzing as best you can why you failed and what you can do better next time. Earn your successes. Realize that you’ll never be good at storytelling. Not you in particular. Anybody! Updike, Fitzgerald, Shakespeare … — our greatest storytellers — all knew that the only worthwhile method was to keep trying and failing, trying and failing. Tips will help (see below), but please keep this paragraph always in the forefront of your mind. 

What happens next?

The number-one ingredient for a story is the tension of an unsolved mystery. Stories set up a questions and delay answering them. The simplest example is a question in the first sentence with the answer delayed until the second sentence:

"You know who Bob’s favorite singer is? Meatloaf!"

That’s not a very interesting story, I know, but compare it to this:

"Bob’s favorite singer is Meatloaf."

The first version evokes (just a little) tension. The second doesn’t. 

Now imagine telling the first version but walking out of the room after the first sentence:

"You know who Bob’s favorite singer is? —– "

That agony is what you should strive for. Because the most basic human urge that makes us want to listen to stories is the need to know what happens next. 

Curiosity is the juggernaut that drives storytelling. 

If you immediately tell us what happens next — or if there is no next ("Bob’s favorite singer is Meatloaf") — then there’s no hook. 

Practice this simple question-delay-answer structure over and over, in all your communications. I mean in emails, text-messages, Quora posts, and so on. You’re not going to become a good storyteller by learning how to go into storytellingmode. Instead, turn yourself into someone who tells stories all the time. May stories a natural part of the way you communicate. 

I don’t mean you should start emails with "Once upon a time…" I mean you should always be aware of posing a question, pausing, and then answering. 

"You bet I’ll come to your party tonight, and I’m going to bring something tasty! My grandma’s snickerdoodles!"


A question needn’t end with a question mark. You goal should be to make the reader or listener ask a question. You can do this by asking for him (as I did above), or you can use mystery to plant a seed in the reader’s mind which will sprout into a question after it’s watered by his natural curiosity. 

"Bob doesn’t like the same bands as his friends. He likes Meatloaf!"

Again, imagine saying just "Bob doesn’t like the same bands as his friends" and then walking out of the room. Immediately, I’m wondering "Why not?" and "What bands does Bob like?"

Keep the mystery ball in the air!

If your story is done after "Meatloaf," you’re set. If there’s more, remember toalways engage curiosity. Avoid this:

"Bob doesn’t like the same bands as his friends. He likes Meatloaf! He hates the Beatles or Jennifer Lopez. Actually, he doesn’t listen to much music at all. He’s more into sports. He lives in Chicago, and…"

As I’m reading that, my mind is starting to wander, because there’s no new question — no mystery. Nothing to make me wonder what’s going to happen next. 

This is better:

"Bob doesn’t like the same bands his friends liked. He likes Meatloaf! But there’s one Meatloaf song he hates —"

 Ah! A new question!

As a storyteller, your job is to keep the sense of mystery afloat. There must be unanswered questions right up until the end, and when all questions are answered — or you’ve left us with a big, exciting, never-to-be-answered question* — the story is over.

* loose ends are for storytelling ninjas. There’s a razor edge between satisfying and unsatisfying loose ends. As a beginner, you might want to avoid ambiguous endings until you master simpler forms.

Beginnings, middles, and ends

Many people have posted about this basic structure. In my original Meatloaf example, there was just a beginning and an end, which is fine for two-sentence stories. 

There are all sorts of ways beginnings, middles and ends function. But a basic job they do is to pose a question (beginning), delay (middle), and give the answer (end). Middles create tension by forcing the listener to wait for the answer to the question.

"Bob doesn’t like the same bands as his friends. They’re all into Miles Davis and Charlie Parker. He likes Meatloaf!"

Middle for diddle

Of course, the middle can’t be arbitrary:

"Bob doesn’t like the same bands as his friends. February is the second month of the year. He likes Meatloaf!"

It must add new information, as it did above when I explained what Bob’s friends like. And if a middle goes on for any significant length of time, it must contain its own questions and answers.


"Bob doesn’t like the same bands as his friends. They’re all into Miles Davis and Charlie Parker. One has every Parker album ever released. Another one doesn’t own any Parkers, but he has about half of Miles Davis’s albums. He doesn’t have "Kind of Blue," because he considers it overplayed. Bob doesn’t care if it’s overplayed or underplayed. He likes Meatloaf!"


"Bob doesn’t like the same bands as his friends. They’re all into Miles Davis and Charlie Parker. One friend, Jerry, who is out of work and almost destitute, found a rare Miles Davis album on sale for seven-hundred dollars. He sold his car because he had to own every record Miles Davis ever released. Bob wouldn’t have sold a can of beans for it. He liked Meatloaf!"

Because I told a lengthy middle about Bob’s friend, I knew there had to be questions in it. (What’s Jerry going to do to get that record?) Without questions, stories splutter and burn out. 

Earn your sidetracks

I’ve been exaggerating to make some points. The truth is, we’ve all heard and read great stories that contain descriptive passages without endless question. If you want to spend five minutes of your story time describing a mountain you saw in Japan, that’s fine. But you have to earn the right. You earn it by — guess what — posing a question before your description. The more enticing the question, the more time you earn for your sidetrack.


"There’s this mountain in Japan that’s really high. It takes several hours to climb. I got tired just walking around the base of it. I never wound up climbing it, because I was too scared, but this other guy I met did. He said it was exhausting…"


After visiting Japan, I went somewhere really exciting. But first I want to tell you about this mountain in Japan. It’s really high. It takes several hours to climb…"


"I lost my virginity in Italy. Two weeks earlier, in Japan, sex was the furthest thing from my mind. I saw this really high mountain. It takes several hours to climb…"

Because I have a dirty mind, I want to know who you had sex with and how it went. So I’ll stay with you for the Japanese mountain, waiting for you to got to the Italy part. 

Of course, you have to somehow tie the mountain into the sex experience, or I’ll wonder what the point was. But the most important thing is for you to experiment with earning sidetracks. How long a sidetrack does a particular unanswered question buy you? You have to practice to learn that sort of thing. (Go back and reread my first paragraph.)

Make sweet, sweet love to me or pee on my face

You must make your stories sensual. I don’t necessarily mean sexual. I mean you should constantly evoke one or more of the five senses. Writers often talk about images, but sounds, smells, tastes, and touches work just as well. Humans experience through their sense organs, so the more you can tie your story to sensation, the more vivid it will be. 

This does not mean stating an abstraction and then tacking on a sensation:

"Bob loved all Indian food — he would devour tandoori chicken and licked the orange spice off his fingers."

Sometimes that’s unavoidable, but, if possible, move the sensual to the forefront:

"I’ve seen Bob eat eleven tandoori chicken legs in one sitting, licking the orange spice off his fingers."

You can get into trouble, boring the listener with endless details instead of taunting him with unanswered questions. Unlike the orange yum Bob is licking from his fingers, details shouldn’t generally be added for spice. Rather, you should tell your story with details. 


Beginning storytellers tend to get derailed, forgetting key details. When they realize they’ve goofed, they have to awkwardly insert the missing details later, sometimes after the story is over.

"… and so Bob stayed in his room for three days! (Pause.) Oh, shiet! I forgot to tell you that his house was being fumigated. Damn! Guess I ruined that story! Jesus! I just can’t tell stories!"

We’ve all heard that happen or it’s happend to us.

Well, you’re no longer allowed to let it happen to you. You can’t stop yourself from forgetting details. But your assignmentnow is to recover as best you can and go right back into storytelling mode:

"… and so Bob stayed in his room for three days! (Pause.) Oh, shiet! I forgot to tell you that his house was being fumigated. That’s right! Workmen had covered his house with one of those giant tarps, and they’d warned him to stay out. His whole house was filled with toxic fumes, but Bob wedged a towel under his door…"

SInce you’re learning (and you should always be learning), the worst case scenario is that you start over again. That may be embarrassing, but do it anyway. "Sorry. I screwed up the story. But I really want to tell it. Can I start over?" Your friends will say yes. 

You are not allowed to fail.

You are only allowed to fail and try again.

Front-load your stories with key information

"This amazing thing happened to me, yesterday, when I was on my way to the bank — you know, that one Eighth Avenue, by the Starbucks? Anyway, this was at about three o’clock or maybe three-thirty. What time did we meet for drinks? Four? It must have been earlier, then…"


Even if you can’t help spluttering and digressing, try to give your listener some information upfront: who, what, and a question if possible. That way, the worst case scenario is that the derails will build some tension:

"You’re not going to believe who I met, yesterday! Bob! He was carrying this huge, bulky package. I was on my way to the bank — you know, that one on Eighth Avenue…"

Tell it again and again and again

Good storytellers refine their tales. Make sure you’re not trying to tell new stories every time. Stories get better and better through retellings. I can’t always remember who has sat through one of my stories in the past, so I ask: "This funny thing happened to me when I flew to Oregon. Have I told you this? No? Good…"

Sometimes someone says, "Yes, but tell me again!"