How to Break the Rules of Writing

How to Break the Rules for WritersHere at Writer’s Digest (and despite the There Are No Rules moniker of this blog), we talk a lot about doing things by the book—from understanding grammatical and structural writing rules, to following submission guidelines, to otherwise conducting yourself like a pro. And that’s why we had so much fun putting together the latest edition of WD: “The Rule-Breaker’s Issue.” In it, you’ll find plenty of ways to put all that straightforward advice aside and instead challenge yourself to take smart risks that can pay off—for both your craft and your career.

To celebrate the release of this new July/August Writer’s Digest (on newsstands right now!) I’ll share some of my favorite tips—and give away one free copy to a random commenter below.

3 Ways to Get Ahead by Breaking the Rules for Writers

1. Realize that great writing starts with an appetite for life. Ideas and real-life experience to inform your writing are everywhere—but the most compelling ones may not be out in the open, plain for anyone to see. So don’t be timid: Say yes to opportunities that come your way—even (especially) the strange ones. Sneak backstage. Do something that makes you nervous. Try stepping outside your comfort zone, and you’ll find that the benefits far outweigh the discomfort of your sweaty palms. This tip lies at the heart of Elizabeth Sims’ wonderful article “The Reluctant Risk-Taker’s Guide to Filling the Creative Well.” Here’s one of my favorite parts:

Eavesdrop. It’s illicit, it’s impolite, and it’s great fun. … I used to do a lot of writing at a particular Starbucks in my town. Once in a while I’d see a certain type of couple: a young man sitting drinking coffee with a much older woman. Their conversations were quiet and remarkably intense. And I saw this over and over, with a different young-guy-older-woman combo every time.

I started to wonder. And I started to purposefully, stealthily eavesdrop. I started to look at the bigger picture, and realized that the coffee shop happened to be across the way from an armed forces recruitment center—and these young men and … their mothers had just been there. They’d come out and seen the Starbucks and decided to come in and talk it over.

The faces I saw and the conversations I overheard there were too intimate to recount here, but they informed me as a writer.

Eavesdrop. Write it down. Repeat.

2. Don’t be afraid to twist your plot. Yes, they seem intimidating, but readers love them—and the process of crafting them is not as mysterious as it may seem. Start by thinking of plot twists in more defined terms, and understanding the elements that make them work so well. For a twist to be effective, it needs to be four things:

  • Unexpected
  • Inevitable (in retrospect, the only possible ending to that scene, act or story)
  • An escalation of what preceded it
  • A revelation that adds meaning to what has already occurred.

The idea of twisting your plot sounds more quantifiable already, doesn’t it? This tip comes from Steven James’ “Pulling the Rug Out,” his detailed guide to twisting your plot using seven simple keys. It’s one of my favorite craft pieces we’ve published in recent memory—in fact, I’ve never seen another one quite like it. Writers of mysteries, thrillers and suspense especially will not want to miss this issue for this single article alone.

3. Challenge yourself to try a new genre. This issue’s WD Interview subject, Adriana Trigiani, has succeeded in genres almost too numerous to name. She started out writing for TV (if you ever watched “The Cosby Show” or “A Different World,” you’ve enjoyed her work) then moved on to series novels (her Big Stone Gap books and Valentine trilogy are book club favorites), and has since written nonfiction, YA, and her latest, her most ambitious work yet: the sweeping epic novel The Shoemaker’s Wife, which spans multiple generations of Italian immigrants and is based on her grandparents’ love story—and which, by the way, has remained on The New York Times bestseller list since its April release. In our inspiring interview, she admits that her new book took her way outside her comfort zone (“When I gave the first few chapters to my editor, I was sick to my stomach,” she told WD. “I thought, Oh my God, is she going to think this is the worst thing she ever read?”) and encourages other writers to fearlessly push their writing in new directions. “Look at me,” she says. “I found something I love because I tried it. Don’t be afraid to shake it up!”

Giveaway: Win a Free Copy of The Rule-Breaker’s Issue!

These are just three of many unconventional tips you’ll find in this issue. It also features a guide to rewriting the rules of marketing your own work (featuring a “Rule-Breaker’s Spotlight” Q&A with Cheryl Strayed, author of Wild, Oprah’s newest book club pick), a fascinating piece on why you might actually be better off ignoring well-intended advice you’ve heard about writing conferences, and an insightful profile of House of Sand and Fog author Andrea Dubus III, whose approach to the craft is inspiring in its sincerity (“Even a day writing badly for me is 10 times better than a day where I don’t write at all,” he told WD).

Want to win a copy? Leave a comment below telling us which of the so-called “rules” for writers you’ve been looking for a good excuse to break (whether it’s an implied rule, a commonly accepted one, or anything in between)—or just share any other reason at all that you’re excited about this issue. One commenter will be chosen at random to receive a free copy.

You can also preview and/or order the full July/August Writer’s Digest here, find it on your favorite local newsstand, or download the complete issue instantly.

Jessica Strawser
Editor, Writer’s Digest Magazine

Follow me on Twitter: @jessicastrawser

Like what you read from WD online? Subscribe today, so you’ll never miss an issue in print!

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33 thoughts on “How to Break the Rules of Writing

  1. BOGIE

    I’m glad to know that I’m not the goody-two-shoes most people see me as. I have been eavesdropping for all of my writing life! My curiosity just takes over – but I don’t use the information I gain for evil. So I guess I am a goody-two-shoes. In any case, it’s breaking the rules that makes writing fresh.

  2. leah1964

    I seriously dislike the notion (rule) that you have to be accepted by a big publishing house in New York to be a “serious” writer. Not true! Authors of great and inspiring books shatter this conventional wisdom on a regular basis. I would love to see more articles and discussion along the lines of self/indie publishing on/in Writer’s Digest – it’s the future of publishing.

  3. dtapley

    I agree with those who wish to break the “you must write X words every day.”

    My schedule simply won’t allow that. I prefer to set aside blocks of days devoted to writing, the product of which can then be polished and refined in shorter chinks of time when “real life” returns.

  4. Noodlebug

    I will admit for most of my life I have had trouble breaking any rules. Now Since I started writing in a real sense I have done things that I normally would not have. Stood in the middle of the road for a few seconds longer than I should, eat ice cream after midnight, ride the Farris wheel alone (I’m scared to death of heights), and even jumped from a rope into a lake with my eyes closed. All seem childish for rule breaking but it was those and many other experiences that changed my perspective on life and writing.

  5. pettigrew1966

    Oh…one more thing. I’ve made it a habit to write immediately after divorce or a “break-up”! Besides being therapeutic, some really great stories and ideas are now on paper! Even though I’ve changed the names of the “characters” involved, those poor guys will definitely know who I’m talking about!

  6. pettigrew1966

    After reading this, I am pleased as punch to see that I adhere to 2 of the “non-rules”. I get inspired with new stories when I people watch, eavesdrop, and EVEN “politely” join in the conversations of strangers. It’s quite fun! However, the best advice is to experiment with new genres. Thinking I would ONLY write poetry, I attempted a few short stories which led to essays, to novel ideas, to screen and stage play outlines. BE ECLECTIC with your work and you’ll surprise yourself with new energy and maybe even a new path!

  7. sassy

    I’ve always been a ‘follow the rules’ kind of reporter. Now that I’m working on a literary novel, it’s a novelty to discover I can break the rules and it’s liberating, not just for me but for my characters! Thanks for the article. More, please!

  8. Naomi

    I’d like to break, shred, and put in a compost heap the following rule: your novel must have an over-arching theme. Phooey. I enjoy novels because of the characters: their problems; their foibles; their quirks; as well as their reactions to, and solutions for, various crises.

  9. pmettert

    I would find the twist article interesting. I do twists, but I’m not sure HOW I do them. 😉 I also love to eavesdrop. I have missed big hunks of the conversation at my own table because I am caught up in the one next to me. 🙂

  10. starlitsky

    Show, don’t tell. I like to tell more than most writers do. Not for the longer, more important scenes, of course, but my writing is concise. No fluff.

    Also, the obligatory twist ending. In the novel I’m writing now, I’m aiming for an untwist. A big plot point is that the protagonist does not know the identity of the villain, but it is so obvious (to the reader) which character it is that readers would expect a twist and will be surprised when the obvious answer is actually the correct one.

  11. Godim

    I always try to break the rule of a reluctant hero. My heroes always want to go, to get out of their home/town/comfort zone. But life puts obstacles in their way.

  12. Sharon Henning

    I now have your permission to eavesdrop. I don’t know if it’ll keep me out of hell but maybe it will inspire some interesting stories.

  13. MrsCsays

    I can see myself breaking rule 3. Romance is usually my thing but I can see myself doing some serious drama involving some scandal and mystery. Now my juices are flowing. Thanks for this article.

  14. Ivye

    I’m not dreadfully good at breaking rules – which is probably why I so wish to take the plunge and break a few. 🙂 One thing I would really love to do is to tinker with structures. And yes, I know structure is all-important, and have worked on it a good dead these past years. Now I’m dying to experiment, and do some colouring out of the lines…

  15. Madison AD

    I think the “rule” I’d like to break is a bit of an anti-rule, but to me, it seems rule-ish nonetheless:

    “Just Write” – I used to do this, but I find that it doesn’t lead anywhere useful. For a short story or scene? Sure. But not for a novel. If I “just write” for an hour, I end up with pages of things that are only “okay” (if that), and I despise editing!

  16. thndrstd

    I think the main rule that needs to be broken is relying too much on what people call the rules of writing and simply finding what works best for you.

  17. amesplaza

    My problem is, I don’t believe in breaking the rules until you KNOW the rules. Some of the rules I know really well but others, I don’t. I might stray from a few things I know but I think there are many people who just do whatever they want whenever they want, which makes their writing look ridiculous. I feel like the best rule breakers have to know what they’re doing to begin with.

  18. AaronSBell

    see, my issue with adding a twist is that it is almost so commonplace that it is expected. that causes the twist to lose the desired impact of it happening. there are so few instances of something really coming out of left field to surprise me anymore. if it’s done well, however, it can be brilliant.

  19. Renee Carter Hall

    I’m tired of being told I have to write a certain number of words per day (or write every single day without fail) to be considered a “professional” writer instead of a wannabe or an amateur. For me, writing every day is a failproof recipe for burnout. I feel like it’s more important to understand your own creative rhythm and work within that, playing to your own strengths, rather than binding yourself to rules that work for somebody else and don’t work for you.

    The other “rules” I hate are any notions that, because this is what Famous Author X does, that means that it’s what everybody should do, either in terms of method/process or marketing the finished work. This is not a one-size-fits-all field.

  20. Sean Durity

    Genre-breaking is a good exercise for me. I have written some poetry and short stories to stretch my writing muscles. As for rule-breaking, I am most likely to use a sentence fragment for impact, but only in fiction, so far.

  21. Shinteetah

    Outlining. I’m terrible at it and it seems to stunt my characters. This isn’t to say I don’t have an idea of where we’re going, but I’m open to sudden changes and I very rarely have what anyone else would consider a reasonably structured outline.


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