The Secret Writers Know About Breaking Writing Rules

What’s the dirtiest word in writing? Some might say “rejection,” but according to one of my viewers, it’s “writing rules.”

“Rules,” he said, “are the enemy of true artistic vision.” But is that true?

What if I told you the greatest rule-breakers in history followed the rules first?

Writers who tore down conventions didn’t start by tossing grammar books into the fire—they mastered the craft of writing before dismantling it. Let’s talk about anarchy in writing: the myths, the truths, and how to wield chaos with purpose.

This is a provocative topic. If you gain value from this video, please like, subscribe, share, and comment. I regularly read the comments, and what you say matters.

Are “Writing Rules” a Dirty Word?

A viewer of this channel passionately argued, “Rules are the enemy of true artistic vision.” He said, “The artist’s vision is a unique, non-teachable, sacred expression.”

He added, “Who is to say what is good or bad art? Who decides?”

Interesting! Let’s answer those questions.

Hunter S. Thompson: A Case Study.

He was one of the most iconic modern anarchist writers—and he didn’t reject rules. In fact, he meticulously followed them, at least while learning his craft.

Thompson famously retyped The Great Gatsby and other novels, word for word. Mindless mimicry? Hardly.

Thompson did this to internalize what made those stories compelling. He knew you had to deeply understand the rules to break them brilliantly.

True anarchy in writing isn’t about chaos—it’s mastering the system so you can dismantle it with purpose. By understanding the mechanics of storytelling, Thompson developed the skills to create Fear and Loathing in Las Vegas and pioneer “Gonzo Journalism.”

Inside Allen Ginsberg.

Ginsberg’s masterpiece of anarchist expression, Howl, didn’t emerge from thin air. He spent years studying poetic structure, grammar, and everything else that underpins great writing.

If you haven’t read Howl, do it.

Did you know that Jack Kerouac’s spontaneous novel On the Road wouldn’t have seen the light of day without Ginsberg? On the Road was originally unpublishable, and Ginsberg spent three years rigorously editing Kerouac’s famous scroll.

Ginsberg knew the rules—and he made On the Road fit to publish. Real artistic rebellion isn’t rejecting rules entirely; it’s subverting them to surprise and engage readers.

Many self-styled rebels think breaking grammar rules makes them revolutionary. In reality, it often makes them unreadable. True anarchists use the tools of the craft to amplify their message.

Anarchy in art isn’t about rejecting all rules; it’s about using them as weapons to challenge norms and inspire change.

I love what Andy Warhol said on this topic: “Don’t think about making art, just get it done. Let everyone else decide if it’s good or bad, whether they love it or hate it. While they are deciding, make even more art.”

Is Artistic Vision Sacred and Non-Teachable?

Another claim from my viewer was: “The artist’s vision is a unique, non-teachable, sacred expression.” Is that valid?

Artistic vision isn’t born in a vacuum. Writers, musicians, and painters draw on life experiences, training, and the works of others. Bob Dylan, often hailed as a revolutionary artist, confirmed in an interview that he learned lyricism from folk songs and poetry.

He didn’t wake up one day as a fully formed genius. Inspiration may feel sacred, but it’s the result of internalizing—and then transforming—various influences.

Craft Is Always Teachable

Expression—the ability to translate vision into art—is teachable. Whether it’s learning to make furniture, spray graffiti, or write a novel, every artist hones their craft through instruction and practice.

Singer Madonna once claimed she wouldn’t sell her music catalog because her songs were written under “divine inspiration.”

Well, artistic vision feels sacred because of the effort invested—not because it magically appears. Every creator builds on influences and experience.

A Personal Story

Let me tell you a short personal story. One of my lifelong friends was a well-known American Marxist. Mike and I were Cub Scouts and classmates growing up, and we stayed in touch over the years.

Yes, I believe in democracy and capitalism. I’m a political centrist. I’m a person of faith. But we remained close friends.

Mike was an early member of the radical SDS—Students for a Democratic Society. He was on the front lines of several fiery protests. Later, he wrote several influential books. He was a genuine anarchist—committed to revolution.

Eventually, he became a professor at the University of California. What do you think he taught? Marxism? Class warfare? Open borders? Critical race theory?

If you guessed writing, you’re correct.

He understood that genuine anarchists need to write well to get their message across. Writing is one place where they don’t toss the rules.

Who Decides What’s Good or Bad Art?

The third question from my viewer: “Who is to say what is good or bad art? Who decides?”

This one is simpler to answer. The value of art isn’t determined by a single authority. It’s decided by the marketplace—both the commercial marketplace and the marketplace of ideas.

Successful revolutions transform personal ideas into universal truths that resonate widely. You do that through writing—whether it’s a book, speech, or manifesto.

Ultimately, good art is determined by impact. If it changes how people think or feel, it has succeeded. If your writing fails to connect, it won’t ignite revolutions—no matter how sacred your vision feels to you.

Effective art inspires action and provokes thought.

Rules Are Your Arsenal

Rules aren’t the enemy—they’re the arsenal. If you dream of being a revolutionary writer, don’t let myths about rules or “sacred inspiration” hold you back.

Here’s a dose of reality:

• Master the Rules Before Breaking Them. Study grammar, structure, and storytelling. You can’t create meaningful chaos without understanding order.
• Learn to Transform Ideas. Absorb influences, practice relentlessly, and let your creativity emerge through effort—not from some alleged divine intervention.
• Persuade with Precision. Write to connect, not just rant. The marketplace of ideas demands clarity and actionable steps.
• Most importantly, write with intention.

Writing isn’t just an art or a craft; it’s a means of revolution. Aim your words at the heart of your audience, and you’ll leave a lasting impact.