How to Tell a Great Story

Essential tips from Ira Glass on storytelling

Sergey Faldin
Mar 10, 2020 · 5 min read
Ira Glass. Image credits to SouthBankCentre.

We were sitting in a cafe, drinking coffee.

“You’ve got to have a thesis,” said my dad’s friend from the States, Thomas. “To write a compelling essay, you need a thesis, and then you support that with three arguments.”

Three days earlier, I asked Thomas — as an English native speaker — to help me out with my college essays.

I didn’t know then his advice was wrong on so many levels.

Why We Tell Stories

The ability to tell stories is a human superpower. In Sapiens, Yuval Noah Harari argues that the ability to gossip (or tell stories) is what made humans the dominant species on the planet.

In the War of Art, Steven Pressfield argues that each story has a three-act structure: Act 1 (Setup), Act 2 (Conflict), Act 3 (Resolution). The key to writing a good story is to start at the end and work backward.

Why do we have to have three acts, and not more? Although some stories — like TV shows — can have 8, 10, or 12 acts, the three-act structure is so fundamental to storytelling because that’s how our minds work.

We perceive the world and talk to ourselves through stories. And either you noticed this or not, you always use a three-act structure in your internal monologues. You tell anecdotes to your friends using a three-act structure, too.

Although there are some of us, who are better at telling jokes or anecdotes, humans are all natural-born storytellers. Storytelling is also a skill that you can build and develop.

Ira Glass, the famous host of This American Life show and a veteran radio personality, gives four key tips on storytelling for any creative person.

1. The Building Blocks of a Story

“To write a story, you’ve got to have a statement and supporting arguments,” said your teacher. And while her intentions were good, her logic is stable, there are better ways to tell a story.

The two basic building blocks of a story, says Ira, are:

  1. The anecdote. A chain of events that goes one after the other, after the other. Like a train with coaches. “John went to the bar, grabbed his drink, looked around, saw the girl, waved his hand, and…” (you can feel the suspense right now — what will John do next?)
  2. The moment of reflection. A story is not complete without the reader understand what it means. Use moments of reflection to talk to the reader and describe what the events are leading to, and why they are essential.

“The Power of the anecdote is so great…No matter how boring the material is, if it is in story form…there is suspense in it, it feels like something’s going to happen. The reason why is because literally it’s a sequence of events…you can feel through its form [that it’s] inherently like being on a train that has a destination…and that you’re going to find something…” — Ira Glass

A good story would have the anecdote and moments of reflection, jumping back and forth. You’d start with a story — with action and dialogues to captivate the reader — and then explain what’s happening, then again to the story, then back to the moment of reflection. In a way, that’s precisely how James Altucher writes his blog articles.

A good story would always raise questions and make the reader want to continue reading, wondering what the answer might be.

2. Cut the Crap

“Not enough is said about the importance of cutting out the crap,” says Ira Glass.

The entire team of This American Life show knows that 30% of the stories they come up with are going to be killed. Sometimes more. The creative team comes up with stories with this in mind.

The takeaway here is to come up with exciting ideas, create stories, cut the crap, kill the bad ones, and move on. Don’t dwell on underperforming stories.

Move on.

3. Do a Lot of Work

The most famous piece of advice from Ira, which I wrote about at length, but worth mentioning again.

When you’re starting a creative career, you will go through a long period when your work is disappointing to you. That’s fine.

Ira Glass calls this stage “the gap” — between your taste, which is killer (and got you in the game in the first place) and your abilities, your skills, which are “not that good.”

The worst thing about this gap is not that your work is embarrassing to others, but that it’s embarrassing to you.

The only way to bridge that gap is to do a lot of work. Create a lot of stories. Put yourself on a deadline, and write as much as possible. It might take a lot of time, though. For Ira, it took decades before he became a pro.

4. Be Yourself

When Larry King went live for the first time, on a local radio station, he was nervous. His fingers trembled, and his voice cracked. He went live. But he couldn’t say a word. He was too nervous to talk.

The producer came up to him after the show and said:

“Larry, listen. There is no secret to this business. Just be yourself.”

Ira talks about how he wanted to “sound like a reporter” when he was reporting. But as the years went by and he became better, he realized that the best strategy would be to sound like himself.

When I started my first YouTube show, I wanted to sound like Gary Vaynerchuk (who didn’t?) It wasn’t until I relaxed, and started talking like myself that my content began to attract an audience. My friends noticed, and my girlfriend told me she likes it better when I don’t pretend to be someone I am not.

You might want to sound like a writer you like when you write and copy other people at first. That’s fine. But as Ira says:

“Everything is more compelling when you talk like a human being, when you talk like yourself.”

There’s no secret. Just be yourself.

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Sergey Faldin

Written by

Making sense of the world and teaching others. | Author of: | Reach out:

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +792K followers.

Sergey Faldin

Written by

Making sense of the world and teaching others. | Author of: | Reach out:

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +792K followers.

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