It’s not always easy

Oh I talk a good game. I tell you not to believe in Writer’s Block, the Loch Ness Monster of the word world. But just because Writer’s Block is a myth doesn’t mean it’ll always be smooth sailing when you write.

Take today—well, yesterday by the time you read this. I had to add maybe two sentences to a draft I’d been working on. Two paragraphs at the most.

No, it’s really not always easy

Most days I can turn out 300 words in under half an hour, so this should have been a piece of cake.

Cake…yeah, that’s about the only thing I didn’t eat as I tried to avoid my work. Everything seemed to get in the way: the constant rain (I felt trapped inside), the conference calls that punched a hole in my day, the exhaustion that overtook me as soon as the calls were done.

Did I remember all of Elizabeth Gilbert’s wonderful advice about dealing with fear? Reader, I did not.

Did I remember any of my own wonderful advice about just making your fingers hit the keys, even if all you end up writing is “I have no idea what to write”? Negative.

Did I…yeah I know lists are supposed to have three things in them. But whatever the third thing would be here, you can rest assured I didn’t do that either.

I moped. I pouted. I napped.

I felt like a hypocrite.

It's not always easy

And then I remembered that I’m not a hypocrite; I’m a human being.

So I popped a piece of dark chocolate and I sat my ass down at the keyboard. Well, in my chair in front of the keyboard.

And I wrote what I needed to write.

It may not be the most brilliant work I’ll ever do. But it’s done—and that’s the most important thing.

It’s not always easy. But you can’t let fear silence you.

So write, already.

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Are longer lists better? — Frequent Questions

Q: Are longer lists are better than short ones?
A: [steam coming out of ears] I. Hate. Lists.

longer listsElmore Leonard said writers should always “Try to leave out the part that readers tend to skip.”

If only we could identify those parts in advance, eh?

Well, some of them we can.

Like lists.

I hate lists.

They’re just plain lazy. And did someone say boring? Oh, you bet.

Bullet-pointed lists are meant to impress the reader, I suppose. Ooh—look at all the things! But to me bullet-pointing lists is like going to a networking event and throwing a big stack of business cards at a table full of strangers.

Would you ever be impressed by that? Ooh—hasn’t she been busy collecting cards!

Reader, I’m going to answer this one for you, because I know you’re not idiots. You would not be impressed by that. Not ever. Not only is it unhelpful—just like lists—it’s also downright rude. So don’t give your reader a bunch of things—tell them what’s special about each one.

Lists disguised as sentences at least show a bit more effort on the writer’s part. But they still lump everything together in an undifferentiated mass. If something is important enough for you to mention, it’s important enough for you to tell me why you’re mentioning it.

Longer lists are not better than short

If you insist on making a list, keep it short. And use what writers call The Rule of Three:

Wikipedia very appropriately offers three reasons this rule works. And they’re not presented as a list, either, so 10 points for Wikipedia:

The reader or audience of this form of text is…more likely to remember the information conveyed. This is because having three entities combines both brevity and rhythm with having the smallest amount of information to create a pattern.[2][3] It makes the author or speaker appear knowledgeable while being both simple and catchy.

I added the emphasis there. Now let me translate it into a more readable form: Your list will be more memorable, being shorter. Three is the fastest pattern you can create, and patterns are always more memorable. Plus, you seem smart—while being memorable.

I’d add a fourth use for the Rule of Three, because establishing and quickly breaking a pattern is not only memorable, it can also be damn funny. Breaking the pattern with the third item in the list gets a laugh because the listener recognizes the pattern with the second item and before they even realize they’ve recognized the pattern, you go and break it. For instance, you might imagine a flight attendant going through the airplane asking:

“Would you like coffee, tea, or Xanax?”

I didn’t expect that. Funny!

Breaking the pattern on the fourth or fifth item will only get you a confused stare.

“Would you like coffee, tea, soda, juice, or Xanax?”


The list that ate my headline

Back in the day, I sometimes wrote press releases for a—well, let’s be nice here—an extraordinarily picky client. For a press release about a famous artist, I wrote a headline that mentioned three of this person’s most iconic works. The client added a fourth. And a fifth. Still not enough variety. Pretty soon the headline was a laundry list—one of the longer lists you’ll ever encounter. (Pro Tip: Headlines are not supposed to take up half the page.)

“I don’t like the headline,” the client whined. “It’s too clunky.”


“That’s because you keep adding things to it,” I said. “Keep it to three things and it’ll be snappier”—and I named the artist’s three most iconic pieces.

I don’t remember how many pieces we ended up listing in the final headline, but I think only one of my suggestions made the cut. When the media wrote about the release, though, guess how many pieces they cited? Yes, three. Because journalists know what they’re doing. They also know an iconic image when they see it; all three were the pieces I’d suggested to begin with.

Don’t mess with the rule of three, folks. It’s smart, efficient, and journalist-approved. Tempted to publish longer lists? Don’t say Elmore Leonard and I didn’t warn you.

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Tell them what you’ll tell them: Writing rules to forget

We all remember writing rules we learned in school. The most prevalent must be the “tell them” rule:

  1. Tell them what you’ll tell them.
  2. Tell them.
  3. Tell them what you told them.

I learned this in grammar school—I’m betting you did too—yet I can still recite the rule verbatim.

It’s an excellent example of a sticky idea—shout out to the repetition of “tell them” for providing the stickiness. But as writing rules go, it could hardly be worse advice.

Okay, sometimes style requires an “executive summary” and a section summing up conclusions. But let’s think for a moment about why those sections exist: It’s because no one expects most people to actually read the stuff in between the opening and closing.

Why do so many organizations waste time and resources creating something they don’t expect people to read? Beats me.

But that’s not really my concern. My concern is when this terrible writing advice makes its way from the world of the white paper into the world of presentation.

Yes, I recently heard an otherwise perfectly intelligent woman say during a podcast interview with a speech coach, “I know when you give a speech you tell them what you’ll tell them, you tell them, and you tell them what you’ve told them.” And I started shouting, “NO NO NO NO NO NO!” Fortunately I was alone in the car at the time.

Your poor audience can’t flip pages to escape the triple redundancy. Trapped in their seats, they can’t get up and leave after the “executive summary” of your speech. So in a speech, tell the story ONCE. Tell it memorably and you won’t have to repeat yourself.

Now, if you want to tease the content up front, that’s fine. Generate a little intrigue about what’s coming next. And don’t tell me you can’t “generate intrigue” in an academic context. Actually, the best writers in academia do that regularly.

Writing Rules: Mystery keeps people’s attention

In their book Made to Stick, Chip and Dan Heath tell a story about a study the social psychologist—and noted academic—Robert Cialdini did “to improve the way he talked about science in his writing and in his classes.”

Cialdini examined a range of scientific works aimed at a nonscientific audience. In passages he identified as “unclear,” he found overly formal prose laden with jargon. The clear passages used vivid examples and fluid language. In other words, they were written well. But he noticed something else about the good writing. As the Heath brothers quote him:

“The most successful of these pieces all began with a mystery story. The authors described a state of affairs that seemed to make no sense and then invited the reader into the material as a way of solving the mystery.”

As Cialdini notes, the “aha!” experience is much more powerful if it’s preceded by the “huh?” experience. This is as true in business as it is in academia. So don’t “tell them what you’ll tell them.” Tell them a story, pique their intellectual curiosity.

And if you want to sum up your main points at the end, yes, you can do that. But don’t just cut and paste it from your opening. Weave it into  your call to action. Add something new to the material that further enhances our understanding of it.

If you really need a set of writing rules, here’s mine:

  1. Tell them the beginning of a story.
  2. Tell them more of the story, and why it matters.
  3. Tell them what they can do about it.


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