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The Creativity Paradox: Why Writing That Breaks the Rules Wins in the End

5 min readMar 12, 2025

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Photo by Randy Fath on Unsplash

Have you ever had an idea for an article that felt different, maybe even risky? You hesitated, wondering if people would find it too weird, too unconventional. Or maybe you’ve heard advice like “Write what people expect” or “Stick to what’s proven to work.” But here’s the thing: Truly creative writing often violates expectations before it becomes celebrated.

This is the creativity paradox at play: Creativity has the power to make your writing stand out, but because it challenges norms, it also invites skepticism, pushback, and sometimes outright rejection. The very thing that makes writing fresh and exciting is what makes it hard to accept at first.

Studies show that while creativity is universally praised in theory, it is often rejected in practice due to the uncertainty it brings. Understanding this paradox is key to pushing past the initial resistance and ultimately shaping online writing as a whole.

The Risk of Writing Differently

Think about the most influential writers in history. The ones who changed the game didn’t do so by playing it safe. They defied conventions, experimented with new styles, and wrote what others weren’t willing to.

James Joyce bent language until it became something unrecognizable. Virginia Woolf rejected traditional storytelling structures. Even modern writers who dominate social platforms today — people like Mark Manson or Morgan Housel — stand out because they don’t sound like everyone else.

But before they were celebrated, they were questioned. Joyce’s Ulysses was banned for obscenity. Woolf’s stream-of-consciousness style was considered difficult and strange.

If you look at the online writing world, many of today’s top writers had years of publishing work that barely got noticed. Their approach was too different — until it wasn’t.

This isn’t just a historical pattern. It’s how creativity works in any field: new ideas break the mold, and that makes people uncomfortable at first.

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Photo by Isaac N.C. on Unsplash

Why Creativity Faces Resistance

Humans are wired to prefer the familiar. Psychologists have found that while people say they love creative ideas, they actually tend to reject them in practice, as they subconsciously associate novel ideas with risk and unpredictability, leading them to favor more conventional approaches.

It’s the implicit bias against creativity: we favor ideas that feel safe because uncertainty makes us uneasy.

If you’ve ever published something new and felt like it landed with a thud, that’s why. Creative writing isn’t instantly accepted — it’s resisted, ignored, or met with confusion before it catches on. And that can be discouraging, especially when you see formulaic, predictable content getting more attention.

This resistance is not just personal; it’s structural. Research by Jackson & Gelfand (2019) found that societies with looser cultural norms produce more creative output, but they also experience more instability. Creativity, by its nature, disrupts existing systems, which is why institutions and audiences alike often push back against it at first.

How to Leverage the Creativity Paradox as a Writer

So, what do you do? If breaking norms makes writing harder to gain traction, does that mean you should just stick to the usual formulas?

Absolutely not.

Here’s how you can use the creativity paradox to your advantage:

  1. Understand that resistance is a sign you’re onto something. If your writing gets mixed reactions, it likely means you’re not just repeating what’s already been said a thousand times. That discomfort from readers? That’s part of the process before acceptance. Recent research showed that creative individuals tend to have a higher tolerance for social risk, meaning they persist despite negative feedback.
  2. Create within the gap. The best writing isn’t radically unrecognizable. It balances the familiar with the new. If you break every writing convention, people may not engage. But if you introduce just enough of a creative twist while keeping some elements familiar, you create something fresh but digestible.
  3. Be patient. Creative work often isn’t rewarded immediately. The early years of a groundbreaking writer’s career can feel like shouting into the void. But over time, audiences catch up. What feels strange today can become the new standard tomorrow. Historian Barry Staw pointed out that society tends to “celebrate the victor” in hindsight, often forgetting the early resistance those individuals faced.
  4. Find your early believers. Not everyone will get your writing at first, but you don’t need everyone; you need a core audience that does. The more you double down on your unique voice, the more your people will find you.
  5. Own your creative deviance. Some of the most successful online writers today have built audiences by intentionally defying expectations. They refuse to water down their writing for mass appeal. And, ironically, that’s what draws people to them.
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Photo by Rob Janoff on Wikimedia Commons

The Writers Who Change the Game Aren’t Afraid to Break It

If you want to be the kind of writer who stands out not just in the short term but in a lasting way, you have to be okay with breaking rules. Not recklessly but thoughtfully.

Push boundaries. Experiment. Let your writing be a little uncomfortable.

The paradox of creativity means that your most unconventional work might be met with resistance before it’s met with appreciation. But in the long run, writing that takes risks is the writing that lasts.

So the next time you hesitate before hitting publish because your idea feels too different, remember: that’s exactly why you should publish it.

What’s a popular writing ‘rule’ you think is worth breaking? Or do you have another view of creativity in writing that does not involve breaking the rules? Share below in the comments.

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ILLUMINATION
ILLUMINATION

Published in ILLUMINATION

We curate & disseminate outstanding stories from diverse domains to create synergy. Apply: https://digitalmehmet.com & https://substackmastery.com Subscribe to content marketing strategy: https://drmehmetyildiz.substack.com/ External: https://illumination-curated.com

Samir Jaber
Samir Jaber

Written by Samir Jaber

Wryter with a Y | Helping writers unlock their writing potential | Join my newsletter: wryters.samirjaber.com

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