10 Paradoxes of Story

Happy Saturday. I wrote a 35,000-word book in November (it’s close to done!).

Telling a story – in a book, in marketing, in a presentation – is never simple. There is no ‘one size fits all’ when it comes to tactics or style.

Instead, let's explore the 10 most powerful Paradoxes of Story I’ve found.

Check out past posts here.

The Paradox of Quality

The Creativity Faucet is the idea that creativity is not a limited resource, but rather a constantly flowing source of inspiration and ideas. The more I create and the more I write, the more ideas and inspiration seem to flow.

It is as if the act of creating opens the faucet and allows the creative juices to flow freely, but not at first.

My first hour of writing produced the worst writing. The next two hours improved, one after the other.

Julian Shapiro explains the Creativity Faucet well here and I love Ed Sheeran’s explanation, as well:

The Paradox of The Twist

A twist must be unexpected – a sudden turn of events that catches the reader or audience off guard and leaves them reeling. But a twist must also be inevitable – a logical and satisfying conclusion to the events of the story.

The key, and thus the hardest part, is finding a twist that strikes the right balance between surprise and inevitability. It needs to be shocking, yet make perfect sense when looking back on the events of your story.

The Paradox of Constraints

I used to believe storytelling (and creativity at large) meant no constraints – your mind free to wander onto anything it may please.

Turns out constraints are the key to focusing your creativity and productivity.

I wrote about three constraints here, from Neil Gaiman, which I now use everyday:

• Where you are

• What tools you have

• What activities you allow yourself

The Paradox of Emotion

Pixar ties a unique color to each scene of its movies which ties back to a singular emotion. Apparently, it takes almost as long to nail the colors as the plot.

Storytellers (read: me) often focus too much on the logic of the story – does this event lead to this other event? Would a character actually take that action?

But we focus too little on the underlying emotion, which is what grips the audience and makes them remember the story long after.

An audience forgives faulty logic in a story, but an audience falls asleep with no emotion.

The Paradox of Character

Your character must both be consistent and dynamic.

Your character must change and grow, after all every great story has a transformation at the center of the story.

Yet at the same time, your character must stay true to herself.

The Paradox of The Hero’s Journey

The very essence of adventure and excitement: the Hero faces their fears and overcomes obstacles in order to become the person they were always meant to be.

But… it’s the same structure found in the majority of great stories dating back to the Greeks. In short, if screwed up, it becomes predictable.

The challenge we face as storytellers? Keeping the Hero’s Journey fresh, while remaining true to its core themes and ideas.

The Paradox of The Ending

The conundrum that plagues every storyteller. On one hand, a happy ending is the very essence of story – the triumphant victory of good over evil, of love over hatred, of hope over despair.

But if the ending is too predictable or forced, the entire story falls flat. Your ad, your book, your brand – nobody remembers it.

The key, which I’m still searching for in my book, is to find the right balance between a fulfilling ending, and one that feels earned and true to the story.

The Paradox of Backstory

Backstory gives characters depth and complexity, it provides meaning to your story.

But it’s boring! Backstory slows the pace of your story and can diffuse the tension you’ve worked so hard to build.

Instead, use as little backstory as possible at the start of your story. Then mix it in, when needed, throughout to add context and clarity.

The Paradox of Detail

The bigger, more dramatic your story (or part of the story), the more the little details matter.

Go read the climax of your favorite book. I'm guessing the author includes far more small details when the stakes are the highest.

The Paradox of Curiosity

Curiosity is what keeps your audience invested in your story – it is the desire to know what happens next, to uncover the mysteries and secrets of the story. Without it, the story becomes dull.

But! Introducing too many plot lines quickly becomes overwhelming, both to the storyteller and the audience.

Use open loops to keep your audience interested in one line of thinking. And mercilessly cut unnecessary side quests.

Those are the 10 Paradoxes of Story I've been thinking about. Which resonated the most with you? What did I miss? I’ll include the best replies next week.

Talk then.

– Nathan

A message from... Me!

The interest in this tweet blew me away...

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 StoryWork.

And so many of you liked, commented, and sent me DMs about the practice I decided to turn it into a guided course for you.

Check it out:

Storyteller's Finds

💎 Gem: Bearly.ai has become my new secret weapon. It saves me hundreds of hours of research time for my newsletter and social content by summarizing papers into the bullet-point lists they were meant to be.

🗞️ Newsletter: Stacked Marketer just gets better and better. They've mastered a useful, daily marketing email.

📹 Documentary: Engineering An Empire from the History channel was my favorite docuseries as a kid. I just came across the entire series on YouTube. It's still fantastic.

Career Fair

Growth and content roles are the first to go in recessions. But my talent collective has companies actively searching for Growth and Marketing rockstars.

If you’re open to new opportunities, apply to the collective to get introduced to some of my favorite companies. You can join anonymously (if you want) and leave anytime – completely free. Apply here.

If you're a company searching for top candidates, learn more or request access here.