Don't be a literary prude: How to write with personality

Ian Lurie

I’m reading Writing with Style by John R. Trimble. If you want to learn to write with personality, this book’s a fantastic place to start.

My favorite chapter so far is titled “Superstitions” and begins “This chapter concerns literary prudes.” In it, Trimble describes a few ‘rules’ for writing. I put rules in quotes because I’m talking about the kinds of rules that suck the life out of writing. They’re the ones that grammar school teachers throw at us to prepare us for a colorless, humorless life as a wage slave.

Trimble’s seven superstitions are:

  1. Never begin a sentence with But or And
  2. Never use contractions
  3. Never refer to the reader as You
  4. Never use I
  5. Never end a sentence with a preposition
  6. Never split an infinitive
  7. Never write a one-sentence paragraph

The funniest part is that we learn this in classes with names like ‘Creative Writing’.

Here is the thing: Vanilla rules mean vanilla writing. If one wishes to write with personality, then one should throw superstitions out the window. On, your groove should get.

Egads. Let’s try that again:

Here’s the thing: Vanilla rules mean vanilla writing. If you want to write with personality, throw superstitions out the window. Get your groove on!

The seven superstitions force us to write one way and talk another. They make writing hard work, and they stilt prose to the point where the best conversationalist sounds like a 19th century barrister.


The Seven Superstitions kill writing: A bit of proof

In law school, I got a C—- in legal research & writing. I’d always thought I was a decent writer, and that grade started me on a few years where I really didn’t enjoy writing. Actually, I was in law school. I didn’t enjoy anything.

I started to love writing again when I graduated and went to work in copywriting. Why? I was allowed—encouraged, even—to throw the seven superstitions out the window.

Your assignment

A bit of quick homework for you: Tomorrow, make sure you break every one of the seven superstitions. You don’t have to do ‘em all at once. Drop a split infinitive into an e-mail. Stick a ’but’ at the start of a sentence. Throw in a contraction here and there.

And write a one-sentence paragraph or two.

After a while, I’ll bet you’ll start to like writing again.

By the way, this would count as a way to ‘be authentic‘.

Ian Lurie

Ian Lurie is the founder of Portent. He's been a digital marketer since the days of AOL and Compuserve (25 years, if you're counting). Ian's recorded training for, writes regularly for the Portent Blog and has been published on AllThingsD, Smashing Magazine, and TechCrunch. Ian speaks at conferences around the world, including SearchLove, MozCon, Seattle Interactive Conference and ad:Tech. He has published several books about business and marketing: One Trick Ponies Get Shot, available on Kindle, The Web Marketing All-In-One Desk Reference for Dummies, and Conversation Marketing. Ian is now an independent consultant and continues to work with the Portent team- training the agency group on all things digital. You can find him at

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  1. I have a blog where I try to focus on writing the same way that I speak, and it can be a lot harder than you would think.
    I ran head first into a brick wall with the following line from a recent post. It was perfect in my head, but in writing it lost its flow and seems over punctuated;
    (begin quote)
    I love steak, egg and chips… like seriously. But now I have to eat chicken, steamed veggies and… get this; To make it less bland “a dash of balsamic vinegar!”
    (end quote)
    The tonal inflictions are lost and no matter what I tried, I couldn’t get the rhythm right, so in the end I just posted it, but I want to delete it every time I see it.
    Any advice. Would the book help with the technical problem or writing as you speak?

  2. Writing rules definitely are made to be broken, but I’ll add the caveat that they’re best broken when the writer does so knowingly, using it for style instead of out of ignorance. The latter often sounds uneducated or unprofessional to my ear. And personally, while I’m happy to throw the rules out when it suits me, I still can’t bring myself to end with a preposition or split an infinitive, sorry. 😉

  3. @Ranting I think the book can help regardless, but it goes pretty deep into how to simplify and make your writing more accessible. I suspect that’d help in the case you describe.

  4. Great example Ranting, there seems to be a couple of small issues tripping you up.
    Firstly, I think you just need to define how you use your triple dots (…). I only use them for a pause effect, to gain some impact, or let the reader know that the sentence continues below.
    Something else you could use is the mighty dash (-), this is great to highlight a significant point.
    The semi-colon looks too formal and I don’t really know what you want it to do, probably because they’re not commonly used. Although I find colons can be very useful before a comma-separated or bullet-point list.
    I also find that comma’s can be used in exactly the same way as in formal writing.
    My version would be something like this…
    I love steak, egg and chips – like seriously. But now I have to eat chicken, steamed veggies and get this, to make it less bland… “a dash of balsamic vinegar!”

  5. I’m with Rebecca. Learn the rules before you break them. Isn’t that true of every industry?
    Method vs. Madness: Was your post supposed to be a parody? An apostrophe does not signify plural (comma’s). What were the quotation marks doing around “a dash of balsamic vinegar”? “triple dashes”? They’re called ellipses – and they’re separated by a space both before and after.

  6. Rebecca/Juliette: But who came up with these rules? And why do we trust them for writing for our audiences?
    Ian, if you haven’t already, do check out Rudolf Flesch’s How to Write Speak & Think More Effectively. Loved it! He lists 25 Rules, some of which are completely the opposite of Trimble’s. Like, #2 Use contractions. Or how about #4 Use the first person. #22 Use direct questions.
    Flesch also wrote Why Johnny Can’t Read and another personal favorite, The Art of Plain Talk.

  7. @Method vs. Madness: Thanks for the great advice. I hate it when my prose is littered with too many triple dots (or ellipsis) as that makes it look like it was written by a 13 year old girl.
    For those who would jump on me for using them in the paragraph, I’m using the Comic Strip Ellipsis effect. After all this is a post about breaking to rules for creative effect.
    In this case, I think the space before is not required, as the desired effect is to build anticipation.
    @Juliette: The quotation marks were there to signify that I was quoting the healthy food gurus.

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