Questions & Answers

If your story doesn't answer these 5 questions, you don't have a story

Hey friends,

I’ve gone deep on storytelling structures recently. Last week, we looked at Promises & Payoffs as a more flexible structure compared to classics like The Hero’s Journey, Three Act, etc etc.

Today, we’re talking about five Questions to design your story around.

PS: Thanks to everyone who filled out the feedback survey. If you haven’t, you can do so here. Thanks!

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Maximus is the favored general of the Roman emperor Marcus Aurelius. But, right after Marcus tells Maximus he wants him to be his heir, Marcus dies before it’s made public. Instead, Aurelius’ jealous son takes the crown, kills Maximus’ family, and enslaves him. Maximus rises through the ranks, seeking revenge against the man who betrayed him, while also becoming a symbol of hope for an oppressed people.

Elsa, unable to control her powers, accidentally unleashes eternal winter on the kingdom during her coronation and decides it’s best if she gets out of town. Anna, her sis, sets out to find her and bring her back to end the winter. Her help? An ice harvester named Kristoff, his reindeer Sven, and a talking snowman named Olaf. Along the way, Anna learns the true meaning of love and sacrifice. In the end, Elsa learns to control her powers, the sisters are reunited, and Elsa returns as queen.

You may be wondering, “why did I just read the plots of Gladiator and Frozen?” Good question.

They’re two vastly different stories. One’s animated. The other’s Russell Crowe stomping around Italy. One follows a pair of sisters as they struggle with their parents’ death and coming of age. The other’s a brutal journey from slave pits to the Roman Coliseum.

But, at their core, the two stories answer the same set of questions. And it’s a set of questions you can use, too.

The 5 questions every great story answers

“Remember, the essence of storytelling demands that we place our main characters on a path. A quest with something at stake, with something to do, to achieve, to learn, and to change.” — Larry Brooks

1. Who is your main character(s)?

The person who goes on the adventure. The person with something at stake. The person we’re interested in.

Gladiator: Maximus, the chosen successor of Marcus Aurelius.

Frozen: Elsa, the soon-to-be queen, and her younger sister, Anna.

2. What do they need?

You need something. So do your characters. Give them a need, a desire, a goal.

Make your audience know your characters are worth their time. Give them opinions, strengths, and weaknesses. Even if the audience doesn’t like your character, they’ll be intrigued by her.

Which is more important.

G: Maximus needs to become the hero Rome needs.

F: Elsa needs to come to grips with her magical power. Anna needs to show her sister love.

3. Why can’t they get it?

Tension. Tension. Tension. It’s what keeps the pages turning and the eyes glued to the screen.

Give your audience a reason to root for the character. They don’t want it to be easy. They want your character to struggle. The more, the better.

G: Commodus, the son of Aurelius, murders his father, kills Maximus’ family, and banishes him from the empire.

F: Elsa’s power goes out of control, throwing the land into eternal winter. Anna and Elsa’s relationship has been broken since childhood.

4. How do they overcome?

Robert McKee has an awesome quote: “True character is revealed in the choices a human being makes under pressure – the greater the pressure, the truer the choice to the character’s essential nature.”

As your characters overcome their obstacles, the better a look the audience gets into who they really are.

G: Maximus fights up through the ranks of Gladiators, finally dueling and killing Commodus in the Coliseum.

F: Anna is willing to sacrifice her life for Elsa. This tribute “thaws” Elsa’s heart and brings her back to life.

5. How do they change?

Your character needs to go through obstacles so challenging they’re forced to come out the other side a different person. Highlight that change. I was once this, but now I’m this.

G: Maximus leaves Rome in the hands of the Senate after his death, the symbolic finishing of his quest. Behind him, he leaves a better Rome.

F: Taking her place as queen, Elsa opens the palace gates and shares her magic with her subjects. She went from hiding it within herself, to sharing it freely with others.

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But Nathan, isn’t this selection bias? You made sure to pick movies that fit the questions? Let it go…

Bad pun. Yes, I picked two incredibly successful movies. But this pattern shows up across all kinds of mediums.

Think about your favorite movie (or book or story your grandma told you growing up). Can you answer these five questions? I’ll bet so.

Once you have an idea, this set of questions serves as the building blocks to turn that idea into a story. Each question represents a foundational choice you have to make about your story.

I’ll leave you with three ways you can use these questions:

  1. As an outline. Write the five questions down, then answer each one for the story you’re creating.

  2. As a review. You drafted your story but something’s missing. You’re not sure what. Go through the questions to help find the missing piece.

  3. As practice. Next time an ad catches your attention or a Netflix show keeps you on the couch for a few hours, run it through these questions. Practice spotting story structure in everyday life.


— Nathan

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In my experience, there are two ways to get good at storytelling:

  1. Study the greats (what this newsletter is for)

  2. Practice, practice, practice

I do a lot of practice through what I call 'StoryWork.'

So many of you liked, commented, and sent me DMs about the practice after this tweet that I decided to turn it into a guided course.

Check it out:

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Nathan’s picks

  • Reese Witherspoon turned a book club into a billion-dollar business with an incredible flywheel.

  • How to create a non-boring brand and win users' imagination, a free course from one of my favorite founders.

  • One of you wrote a book… In the vein of Crazy Rich Asians x The Devil Wears Prada, The Fraud Squad stars a working-class woman who impersonates a wealthy socialite to get her dream job at Singapore's poshest magazine. Congrats to Kyla on the launch.

  • The best trend on Twitter is “hilarious product features.”

And a pretty cool dalle-2 image… Elsa entering the Roman Coliseum.

Elsa and the Coliseum