The Best Writers Break the Rules

The best writers break the rules and stray from the common path.

Mark Duffel on Unsplash

The group around the conference table was considering taglines for our new corporate brand. One option in particular was heatedly discussed. I probably shouldn’t disclose the actual line, but it was similar in construction to Apple’s “Think different” tag created in 1997. One member of the group was particularly adamant that we could not use it because it was “grammatically incorrect.”

Ridiculous.

“Think different” also suffered from the same scrutiny, many claiming that different is not an adverb so it should be “Think differently” to be proper. Is “proper” what you want in your writing?

Lawyers are really good at proper writing – dotting every i and crossing every t. They also create mind-numbing text, heavy with clauses, commas, and clutter. I fought little editing battles with corporate lawyers for the last two decades of my corporate career. I wasn’t creating legal documents. I wanted to attract readers and build awareness among investors, employees, and customers.

The tagline example shows what happens when people who think they know a lot about writing get in the way of true writing pros.

Writing is not about rules. It’s about clarity and the sound of the writing. Yes sound. The best writing is lyrical like music, making it flow with a cadence that enhances readability. (Stop yourself now. Legible is not “more correct” than readable.)

The best writing has life. It’s surprising and memorable, not proper or written to please your eighth-grade English teacher.

In fact, I was mistakenly placed into a basic English class in eighth grade. I couldn’t wait to get out of the mind-numbing sentence diagraming and spelling exercises. In a few weeks, the class assignment was corrected and I moved back to advanced English. For the rest of middle and high school I was in either advanced or honors English classes. We practiced writing and studied great writers. We never diagrammed sentences.

I’ve made a career out of writing. What does that tell you?

Some rules to break

You’ve probably heard the following long-standing, often-repeated “rules.” All were either never rules in the first place or should be routinely ignored if it improves your writing.

  • Never end a sentence with a preposition. In fact, the Chicago Manual of Style (preferred by publishers) has never prohibited a preposition at the end of a sentence in any of its versions and editions since 1906.
  • Never begin a sentence with a conjunction, like but or and. Don’t overdo it, but this is often a good tool to emphasize an opposing point.
  • Don’t use contractions. Maybe when you’re writing to an international audience. Otherwise, why sound like a robot rather than writing in a way that humans actually speak?
  • No one-sentence paragraphs. This is a great technique for pulling a key point out into the “open” where people are sure to see it, rather than burying it in a longer paragraph.
  • Write in complete sentences only. If it adds emphasis or cadence, please break this rule.

The fundamentals still have their place

This is not to say that you can throw out every writing rule. Musicians can improvise better riffs when they study music theory. Artists can create more moving pieces when they are grounded in the basics of line, form, light, and perspective. The best writers know structure and composition fundamentals so they know where to break away from the rules to make prose instead of text.

Writing a lot helps you get better, but doesn’t necessarily mean you’ll become a great writer. Malcom Gladwell is credited with conceiving the “10,000 hour” rule in his book Outliers. Widely misunderstood is that it doesn’t mean automatic mastery with 10,000 hours of practice. It does not say geniuses are made, not born. Gladwell has clarified that the rule means that it generally takes that long for natural talent to fully manifest.

I played hockey. Though I probably spent 10,000 hours on the ice, it never made me into Wayne Gretzky. The point is that the best at anything have more talent to start.

Writing is a rare skill and takes years to acquire. Unless you are sure you’ve got that level of skill, hire a professional to help elevate your messages above the rest.

Surprise your reader

As Chip and Dan Heath found in their studies of ideas and messages, “unexpected” is a key element to engaging your audience. Their bestselling book, Made to Stick: Why Some Ideas Survive and Others Die, explains that the best way to get attention for your message is to break a pattern. That’s just what we’re talking about here. Break a rule and jar your reader from what they expect is coming next.

Arthur Plotnik, author of Spunk & Bite: A Writer’s Guide to Bold, Contemporary Style, said it very well:

“When too tightly leashed, writing chokes and loses its vitality.”