Hello Reader!

When my daughter texted to ask if I wanted to go see The Princess Bride at Red Rocks a few months back, it was an immediate “HELL YES!!”

The Princess Bride is a favorite film in our family (isn’t it everybody’s?), although not for the reasons you might think. My teenage celebrity crush was Tom Cruise (ick, I know…it was before the couch jumping), but my sister’s was Cary Elwes. My memory is fuzzy, but I’m almost certain that the whole reason we saw this movie in the first place was because it was part of her effort to see every movie he was in.

It’s a cult classic and lord help me if they try to remake the absolute perfection that this film is.

Also, Film on the Rocks is an absolutely amazing experience. It’s like inviting 9,500 of your best friends over to watch the movies you can quote from end to end, and everyone does and no one gets mad. And even though you get winded getting to your seat, the view is also incredible. 15/10, definitely recommend if you're in Denver in the summer.

So as I’m yelling, “Hello. My name is Inigo Montoya. You killed my father. Prepare to die,” with all my new besties, I’m realizing that The Princess Bride is the perfect film to talk about my favorite topic: Circular storytelling.

The plot of the movie is for Wesley to rescue his true love Buttercup from the evil Prince Humperdinck. We also get Inigo’s vengeance storyline, the Dread Pirate Roberts lore, the sick grandkid and his grandfather, Prince Humperdinck’s plan to start a war, and Vizzini’s inconceivable belief in his own intellect. And yet these side quests are what make this movie so incredible.

Nobody watches The Princess Bride and thinks, “Can we get back to the plot already?” The audience never gets frustrated because they trust that the storyteller knows where they’re taking us. A side quest only works when it ultimately connects back to the main quest.

Aside from being one of my favorite scenes in the whole movie, this is one that feels superfluous, but has small reveals that bring us back to the main plot.

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So many storytellers get fixated on telling a linear story that they miss using the craft that adds dimension: the seemingly unrelated stories that connect in the end. I’m giving you permission to include the weird anecdote, the tangential thought, the childhood memory, the thought that doesn't obviously advance the point…because it all anchors back to your center.

Linear storytelling brings an audience from Point A to Point B. It often looks and feels very flat.

Circular storytelling orbits the idea, sometimes doubling back over itself. Instead of directly explaining an idea, it explores it. It gives the idea dimension. It creates meaning. It adds memorability.

Each story, memory, or observation becomes another piece to support an idea until the audience arrives at a conclusion on their own. Instead of telling people what to think, you're helping them discover it for themselves.

But the secret to circular storytelling isn't having a compelling side quest. It's having a strong enough center that every side quest eventually leads back to it.

That's why The Princess Bride works. The movie has all kinds of subplots, but it never loses sight of its core.

Circular storytelling isn't about taking your audience off course. It's about leading them around an idea until the conclusion feels inevitable.

Try this

Think about a story you're currently writing, telling, or refining.

Before you worry about the beginning, middle, or end, ask yourself:

What is the central idea I'm trying to help someone understand?

Write that idea at the center of a page. Then around it, jot down:

• a memory
• an observation
• a conversation
• a lesson learned
• a seemingly unrelated anecdote

For each one, ask:

How does this help my audience connect to my core idea?

If you can't answer that question, it’s likely a distraction. If you can, congratulations, you've found a side quest.

Until next week,

P.S. I’d love to know, who is your favorite character from The Princess Bride and why? I’ll go first. Mine is Fezzik, because he's presented as this big, gnarly brute, but he really loves his people and is a total softie.