By Ann Gynn published March 14, 2017

Ann Handley on How to Make Your Writing ‘Ludicrously Spectacular’


Best-selling author Ann Handley has the secret to level-up your writing skills. She shared it at Content Marketing World. Now, I share it with you.

Many of us might think that the secret to becoming a “ludicrously spectacular” writer is magic. Or an innate talent or gift. But Ann gave us the cold reality: To be a better writer requires showing up every day and doing the work.

And with that realization understood, she took off to reveal the five levels of her writing pyramid and some tools to help along the way.

Level 1: Don’t write

The level that should consume most of your time doesn’t look anything like writing. Yes, the foundation of good writing is not writing but thinking and researching.

Writing is NOT the foundation of good writing. It’s thinking and researching, says @annhandley. Click To Tweet

At this stage, you embrace the writer’s spirit animal — the squirrel. You are a scatter-hoarder, collecting ideas like acorns and saving them in various places — digital and physical.

Then, you take the idea and research “the daylights out of it,” using Google, including its Books and Scholar options, and other available tools.

Level 2: Create an ugly first draft

Don’t stare at the blinking cursor on a blank page in Word. Don’t even think that you’re writing. Tell yourself something like:

  • I’m just making a list of key points.
  • I’m writing an email.
  • I’m only outlining my ideas.

Or record your thoughts and then transcribe them. Find what works for you and, sooner rather than later, that blinking cursor will be farther down the screen.

If your inner critic is loud, muzzle it with a distraction-free writing tool. While Ann lists a bunch in her book Everybody Writes, three of her favorites are Draft, OmmWriter, and Ulysses.

The main idea here is to stifle your inner critic and your inner editor; instead, just get a bunch of ideas and words on the page in whatever way you’re able.

Level 3: Screw and do

Pick one key point (the screw) and make it easily accessible to the reader. As Beth Dunn, a writer at HubSpot, explains, “The screw is the fixed point around which everything else turns.”

Always ask (and answer) what’s in it for your audience — that’s the gateway to pathological empathy for your reader.

To ensure that your writing is focused:

  • Self-edit by chainsaw — make each paragraph earn its keep.
  • Self-edit by surgical tools — make each sentence earn its keep.
  • Self-edit for voice — make sure the text sounds like a real person with a point of view (more on this in Level 5).
Edit by chainsaw & surgical tools. Make each paragraph & sentence earn its keep, says @annhandley. Click To Tweet

Level 4: Spend the most time on the first line

Ann confessed that she obsesses more about the first line than anything else in her content, including the headline. The first line either makes people want to read further or stop reading right then. Remember, readers are looking for reasons NOT to read your content.

I obsess more about the first line than anything else in my #content including the headline, says @annhandley. Click To Tweet

Ways to make an enticing first line include:

  • Putting your reader into the story
  • Asking a question
  • Quoting a crazy bit of data
  • Telling a story or personal anecdote

Level 5: Find and use your voice

Though we read in silence, we hear the words in our heads and form opinions. We listen to decide if they resonate. Your voice is what separates your content from your competitors. Think of it this way, if you took your brand label off your content, would you know it was your content? Would your clients know?

Your voice is what separates your #content from your competitors, says @annhandley. Click To Tweet

To identify your brand personality, answer these three questions:

  • Who are you?
  • Why do you do what you do?
  • What are you like to deal with?

Here’s how Uberflip defines its brand voice:

Uberflip in 3 words

Uberflip also has a well-detailed style guide. Ann encourages all to steal from it to create their own brand style guide.

In developing your voice, consider detailing elements such as:

  • Tone
  • Word choice (short or long, colorful, serious, etc.)
  • Sentence and paragraph length
  • Analogies
  • Accessibility


The caveat to all of Ann’s tips is that you should not forsake substance for style. Keeping that in mind, I now ask you to take The Writer’s Pledge shared by Ann in her presentation. Put your left hand on a dictionary and raise your right hand, and say these words loudly (or silently, in your head, if you’re not alone and don’t want others to wonder what the heck you’re doing):

  • I will collect and hoard five ideas a day.
  • I will not hit the backspace while I’m writing.
  • I will not go straight from writing to publishing.
  • I will have pathological empathy for the reader.
  • I will not sound like everyone else.

Are you ready to do the work every day? If so, make sure to block out Sept.  5-8 — take a break from the daily writing work and learn a lot at Content Marketing World in Cleveland, Ohio, and hear what Ann Handley has to say in September 2017. Use code BLOG100 to save $100 on early-bird pricing. Register today!

Cover image by Joseph Kalinowski/Content Marketing Institute

Author: Ann Gynn

Ann Gynn edits the CMI blog. She also serves as the Tech Tools editor for Chief Content Officer magazine. Ann regularly combines words and strategy for B2B, B2C, and nonprofits, continuing to live up to her high school nickname, Editor Ann. Former college adjunct faculty, Ann also helps train professionals in content so they can do it themselves. Follow Ann on Twitter @anngynn or connect on LinkedIn.

Other posts by Ann Gynn

  • Susan Moeller

    I loved this talk at CMW, and I think it is one of the best descriptions of the writing process ever! Great summary, and a super reminder to do the work of writing.

    • Ann Gynn

      Hi Susan — Glad to hear you enjoyed it at CMW and the summary today. I find Ann Handley’s tips helpful when I’m in a writing slump. They give me a fresh perspective on the questions I should be asking before/as/after I write.

      • Ann Handley

        Thank you, Susan and Ann. And a special thanks to you, Ann, for taking such great notes during my 2016 talk! Hope to see you both this September at CMWorld!

  • heidicohen

    Every writer should listen to whatever Ann Handley says about writing. It’s pure gold.

    I particularly love the suggestion–I will collect and hoard 5 ideas a day and writing without editing The First Ugly Draft.

    Happy marketing,

    Heidi Cohen
    Actionable Marketing Guide

  • Amanda Maurer

    Thanks for the great post about writing Ann!

    I especially like when you talked about “embracing the writer’s spirit animal — the squirrel.” I think that when I am writing content for a blog post, e-newsletter, or social media post, I get stuck because I’m so focused on getting out the finished product. But I need to slow down and gather information and make a plan first.

    Thanks again!

    • Ann Handley

      Love it! Thanks, Amanda.

  • Vladimir Covic

    I’m just reading her “Everybody Writes”. if you have any doubt about content writing, Ann Handley’s advice should be your go-to. Great author.

    • Ann Handley

      Thanks, Vladimir. I appreciate the generous endorsement!

  • Peter Gearin

    I will not engage in ludicrously spectacular hyperbole! (Aside from that, this is a helpful piece.) Cheers

  • Salim Bensada

    ”Everybody Writes” is not the Must read book It’s the that’s all you need book about content writing. Thanks Ann.

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  • David Boozer

    Hey Ann, this was great! I have read Everybody Writes 2x and starting it again!


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  • Aniruddha Sastikar

    “The foundation of good writing is not writing, but thinking and researching.” I so agree with this, Ann. Wonderful post. Thank you so much.

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