12 Grammar 'Mistakes' That Make Your Copy More Human: Breaking Rules Strategically
Right, let's get something straight. That red pen your teacher wielded like a weapon? The one that circled every misplaced comma and split infinitive? It's time to put it down. Because here's the thing: the best copywriting breaks rules on purpose. And your bank balance will thank you for it.
I'm not suggesting you throw all grammar rules out the window (please don't – my inner perfectionist would never recover). But what if I told you that strategic grammar "mistakes" could actually make your copy more magnetic, more human, and a whole lot more profitable?
Intrigued? Let's dive into the 12 grammar rules you absolutely should be breaking if you want your copy to connect, convert, and create proper relationships with readers.
1. Starting sentences with conjunctions (And yes, it's absolutely allowed)
Remember when Mrs Smith told you "never start a sentence with And or But"? Well, she was keeping you from one of the most powerful tools in conversational copywriting. And here's why...
Starting with conjunctions creates flow. It mirrors natural speech patterns. It pulls readers through your copy like they're having a chat with their best mate. But most importantly? It breaks up the monotony of traditional writing structures.
When to use it: For emphasis, creating conversational tone, connecting ideas naturally
When to avoid: Formal proposals, academic writing, legal documents
Pro tip: Use sparingly – like salt on chips. Too much and you'll spoil the flavour.
Want more conversational techniques? Check out my post about the kitchen table test.
2. Embracing sentence fragments (For impact. Obviously.)
Short. Punchy. Powerful.
That's what sentence fragments deliver. They create rhythm. They emphasise key points. They make your readers pause and pay attention.
Why? Because sentence fragments stand out. They disrupt the pattern. They force readers to slow down and really absorb what you're saying.
When to use it: Headlines, key benefits, call-to-actions
When to avoid: When explaining complex concepts that need full context
The secret sauce: Use fragments for emotional impact, full sentences for information.
3. Ending sentences with prepositions (Something to cheer about)
"Never end a sentence with a preposition" – the rule that makes perfectly natural sentences sound like they've been through a linguistic washing machine.
Compare: "What are you waiting for?" vs "For what are you waiting?"
One sounds human. The other sounds like you're auditioning for a period drama.
Winston Churchill supposedly said, "This is the type of arrant pedantry up with which I will not put." He was taking the mickey out of this exact rule. Be like Winston.
When to use it: Whenever it sounds more natural
When to avoid: Ultra-formal contexts, academic writing
Brand voice tip: This is how people actually speak. Use it to create that coveted conversational tone.
4. Contractions: Your shortcut to sounding human
"We will help you succeed" vs "We'll help you succeed"
One's a robot. One's a human. Guess which converts better?
Contractions instantly make your copy more approachable. They're the difference between sounding like a stuffy corporation and sounding like a helpful friend.
When to use it: Website copy, blogs, social media, emails
When to avoid: Legal docs, ultra-professional settings, instructions that need absolute clarity
Conversion hack: Use contractions in your CTAs. "Let's get started" outperforms "Let us get started" every time.
5. Strategic repetition (Because repetition works. Repetition really works.)
Your school papers probably came back with "repetitive" scrawled in the margins. But in copywriting? Repetition is your secret weapon.
It's not just fast. It's blazing fast. It's your-competitors-can't-keep-up fast.
See what happened there? Repetition for emphasis. Repetition for memory. Repetition for persuasion.
When to use it: Key benefits, important messages, brand mantras
When to avoid: When it becomes noise rather than music
The golden rule: Repeat for rhythm, not redundancy.
6. The intentional run-on sentence (when you need to mirror stream of consciousness)
Sometimes you want to capture that feeling when thoughts flow into each other and you're trying to explain something important and everything connects and suddenly it all makes sense.
That's when an intentional run-on sentence works magic. It creates urgency. It mimics natural thought patterns. It draws readers in.
When to use it: Storytelling, emotional appeals, creating momentum
When to avoid: Technical explanations, instructional content
Balance tip: Follow long sentences with short ones. Like this.
7. Rhetorical questions without answers (Curious how this works?)
Ready to transform your brand voice? Tired of copy that sounds like everyone else? Want to connect with readers instantly?
Rhetorical questions engage readers without needing answers. They create a conversation. They make your audience nod along.
When to use it: Headlines, transitions, engaging readers
When to avoid: When clarity is paramount
Psychology trick: Use questions your audience is already thinking.
8. One-word sentences for emphasis (Magic.)
Simple. Effective. Revolutionary.
One-word sentences pack a punch. They create pause. They demand attention.
When to use it: Creating emphasis, slowing readers down
When to avoid: Complex ideas needing context
Design tip: Give them space to breathe. White space is your friend.
9. Split infinitives (To boldly go where no grammar teacher has gone before)
"To boldly go" sounds infinitely better than "to go boldly". Always has. Always will.
Split infinitives often sound more natural in modern English. They allow for better emphasis placement. They create better rhythm.
When to use it: Whenever it sounds more natural
When to avoid: When it disrupts clarity
Brand voice note: Trust your ear. If it sounds right, it probably is.
10. Creative punctuation (dashes, parentheses, ellipses...)
Standard punctuation = standard thinking. But what if you want to stand out?
Em dashes – like these little beauties – add personality. Parentheses (used wisely) create intimate asides. Ellipses... create anticipation.
When to use it: Adding personality, creating pauses, showing tone
When to avoid: Formal documentation, excessive use
Warning: Don't go mad. Like exclamation marks, these are spices, not main ingredients.
11. Breaking paragraph structure rules (This is its own paragraph)
School taught us paragraphs need multiple sentences.
But sometimes?
One sentence is all you need.
Short paragraphs create white space. White space creates readability. Readability creates engagement.
When to use it: Online content, mobile reading, emphasis
When to avoid: Academic writing, traditional publishing
Mobile-first tip: If it looks good on mobile, it's probably the right length.
12. Casual capitalisation (Because Sometimes It Just Works)
This Is Not How We Were Taught to Write. BUT IT CAN REALLY GRAB ATTENTION. And sometimes, it just Adds Personality.
When to use it: Branding elements, emphasis, personality injection
When to avoid: Body copy, professional correspondence
Brand consistency tip: Create rules for your rule-breaking. Consistency matters.
Why these "mistakes" actually work (the psychology bit)
Your brain doesn't read the way your teacher taught you to write. It scans. It skips. It fills in blanks. Strategic grammar breaking works because:
Mirror neurons activate when we see familiar speech patterns
Cognitive ease increases with simpler structures
Pattern interruption grabs attention
Emotional connection grows with informal language
Authority paradox – breaking rules shows confidence
The golden rules of breaking rules
Master before you break – You need to know the rules first
Be consistent – Develop your own style guide
Clarity trumps cleverness – Never sacrifice understanding
Know your audience – Different rules for different readers
Test and measure – Let data guide your rebellion
When not to break the rules
Sometimes you need perfect grammar. Know when to play it straight:
Legal documents
Academic submissions
Professional reports
Technical documentation
Formal proposals
Ready to break some rules?
Right then. Time to put this into practice. Start small. Pick one or two rules to experiment with. Test them in your next blog post or social media update.
Remember: the goal isn't to break grammar rules for the sake of it. It's to create copy that connects, converts, and builds lasting relationships with your readers.
Need help finding your perfect balance of rule-breaking brilliance? Let's chat about developing a brand voice that's uniquely, unapologetically yours.
P.S. Your English teacher might not approve, but your conversion rates definitely will. 😉
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