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Emily Straubel

Writers’ Rough Drafts – Episode #23 With Emily Straubel


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Emily Straubel is a writer and personal accountability coach who works with overthinkers and over-achievers to help get them out of their heads and into their bodies so they can be healthier, happier and lead the life they truly want. She founded The Red Lipstick Project as a place to talk openly about dating and sex and to connect with other intelligent women who want to find relationships that are as passionate and ambitious as they are. Emily also works with these women as a certified Holistic Health Coach to focus on their health and mindfulness as they go through breakups, job changes, and other transitions to feel and look amazing in their own unique bodies. She’s the columnist behind “The Sex Files,” a blog about dating and relationships on MaineToday.

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Grammar: Why Writing By The Rules Is Killing You

Today’s the day. You’re getting a piece of content back from your editor.

After you work through their suggestions and changes, you can send that bad boy off to be published, sit back, and watch the results.

The editor tells you it’s great, just needs a little bit of work.

“Easy enough,” you say, and open the article. It is then that you remember your editor’s definition of “a little bit” is significantly different than your own.

Marks cover the document. Long-winded suggestions crowd into the margins. Intimidating terminology shows up again and again.  Dangling modifiers. Passive voice. Comma splices.

You recognize a few of the terms, and even understand what some of them mean. They bring you back to your high school or college freshman English classes, when your papers were hacked to pieces by red ink, mercilessly shouting at you.

They’re Grammar errors, and it means you broke the rules.

Rules and Regulations

“Grammar” makes a lot of people cringe. Even some folks who write for a living detest the word. With Grammar comes rules, terms, conditions, exceptions, and a lot of other tiny details that nobody can possibly remember, right?!

Grammar is a massive study.

It’s not just about where you put your commas and periods, or whether your subject and verb match up. It’s used to analyze writing, keep your words clear, and—most importantly—prevent sounding like an unintelligent dweeb to the people you’re trying to convince or debate with.

That’s why it’s so important to study when you go through the arduous process of gaining an education.  Once you graduate high school, or college, or graduate school, you’re thrust straight into the business world—or, for most millennials, straight into the “please read my resume” world—where you have to make a good impression to land a job and be successful in your career.

If you send email with lines like, “HEY, mister charles. whats the 1st meeting time at..???” you may not be fired, but you certainly won’t stand out as the go-to employee for critical decisions.

Starchy, Stiff Writing

So you learn all the tips and tricks of Grammar and all your academic papers are perfect,  hard-earned, Grade A work. Awesome!

Now you’re at your job, at home, writing a book, writing an article, and there’s a Grammar rule that just makes your writing sound… awkward.

This can happen, and it often does. “The house she came from” sounds a lot better—less stiff—than “The house from which she came” (which follows the “don’t end a sentence with a preposition” rule).

There are many times when following Grammar rules to the letter may be structurally correct, but it sounds absolutely terrible from a reader’s standpoint. Nobody wants to be “the stuffy one” in their circles.

The solution?

Break the rules.

Wait. What?

Hang on. You just told me that it’s vital to learn Grammar rules! Now you want me to break them!?


No famous writer, author, or blogger in their right mind sticks to Grammar religiously. It’s insane. You may recall that I said the field of Grammar is massive. To follow all those rules and guidelines to the letter would not only drive you nuts, but it would also erase the most important part of any writer’s work: their individual voice or style.

“When a thought takes one’s breath away, a gram­mar les­son seems an imper­ti­nence.”

— Thomas W. Higginson

Toni Morrison’s popular classic, Beloved, utilizes the “stream of consciousness” style where a character’s thinking is one long stream of sentences, phrases, and words, lacking proper punctuation or structure. She essentially tosses Grammar out the window. Why? Because the voice of the book was more important. It is vital to read this character’s thoughts as an unsettling jumble to better understand them.

You know who Charles Dickens is, right? Well, he broke a grade school rule by writing run-on sentences often in his books. His purpose? Some might say it was to get paid by the word in his writing, but that’s not necessarily true (not all of his writing had that kind of contract). More likely, he did so to emphasize his criticisms of aristocratic parties by satirizing their long, drawn-out, stuffy manner of speaking.

There are many more examples. Sir Arthur Conan Doyle. Jane Austen. William Shakespeare. All of them broke cardinal Grammar rules because it mattered more to get their voice, their style, and their intentions across. If you stick to the rules, but can’t connect with your audience, then what’s the point?

Yeah, What IS the Point?

“Gram­mar is a piano I play by ear. All I know about gram­mar is its power.”

— Joan Didion

Famous writers who broke the rules of Grammar may or may not have been aware that ignoring a particular Grammar rule would make their writing “better.” They just wanted it to sound like their writing. It’s possible they simply thought, “To heck with this rule—I like writing this way.” Sometimes, it’s that easy.

Successful writers do know Grammar. If they didn’t, can you imagine what a disastrous, awkward, confusing, ambiguous mess some of the greatest works of literature would be? The Lord of the Rings series is dense enough—if Tolkien didn’t understand Grammar, getting through all three books would be even more difficult than Frodo’s chaotic trek to Mordor.

Grammar is your map on the journey of writing.

If you occasionally stray off the path because you find a shortcut or a more adventurous route, who can blame you? But if you don’t even bring your map and get lost along the way, your journey will be that much harder without the guide to get you back on track.

Always keep a map of Grammar rules in your back pocket. Refer to them often as you write.

Soon, you’ll know the routes by heart—including the unmarked, hidden trails that make your journey unique.

Tom Morkes

Writers’ Rough Drafts – Episode #22 With Tom Morkes


Or listen on: iTunes | Stitcher | Spotify | Google PlayDownload

Tom Morkes is an author, publisher and professional instigator. He is the CEO of Insurgent Publishing, a boutique, creative publishing platform for the new generation, and the author of multiple books, including the upcoming Collaborate. An Army Veteran,  Tom, along with John Lee Dumas of and Antonio Centeno of launched, a transition resource for aspiring veteran entrepreneurs. He helps innovators start, finish, and ship creative projects by applying what he learned leading troops in combat to entrepreneurship, art, and writing over at reading

Alexis Grant

Writers’ Rough Drafts – Episode #21 With Alexis Grant

Or listen on: iTunes | Stitcher | Spotify | Google PlayDownloadTranscript

Alexis Grant is an entrepreneur, social media strategist, freelance journalist, travel writer and the Founder and Managing Editor of The Write Life, a website that focuses on how to make a living as a writer. She’s worked as a journalist at The Houston Chronicle and U.S. News & World Report, and her work has also appeared in Salon, The Christian Science Monitor, The Chicago Tribune, The Huffington Post, and many others. Alexis now runs her own business, creating and selling digital guides and courses on her website and helping small businesses with blogging and social media. She blogs about careers and the new world of work at

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