The Fascinating Thing About Punctuation Is …

The Fascinating Thing About Punctuation Is …

The fascinating thing about punctuation is … that it did not exist

I get questions all the time about the ‘right’ way to use punctuation, as if there are universal, inherent, absolute and naturally correct ways to use punctuation, as if punctuation has ‘laws’ in the same way that physics has ‘laws.’ It does not.

Punctuation was invented. It is a creative human invention in response to challenges posed by written text.

Today, there are ‘standard usages’ and ‘practical usages’ for punctuation, but those usages are arbitrary.

Not meaningless, mind you, but arbitrary.

I wrote this post for those who get anxious about how to use punctuation. I wanted to write a short but practical overview of the role punctuation plays in writing.

I’m drawing on a shelf-full of books here, but there’s one in particular that deserves a shout-out:

Pause and Effect: An Introduction to the History of Punctuation in the West by M.B. Parkes

Why punctuation?

Imagine you like to shop at flea markets. One day, you stumble across an old notebook. You think maybe you can use it for scrapbooking or collage. You blow dust off the cover and open it. Someone has written page after page of notes.

Here’s what a passage looks like:


This is an approximation of what early written texts looked like. We’re talking about a long, long time ago.

It’s pretty unreadable from our vantage. Then again, it wasn’t meant to be read by just anyone. In The Age of Antiquity, the purpose of writing something down was to record speech. Because it was meant as a record, you would already know (if you were highly educated) what the text said. If you were to read it aloud, you would know where to pause and where to stop.

White Space as Punctuation

Time passed and that meant new readers who weren’t familiar with the text. The scribes responsible for copying these records would insert marks to denote pauses and stops. But there wasn’t anything consistent about the way they marked the text. It was often a matter of personal preference.

Enter the Christians. In matters of theology, interpretation matters. Christian leaders didn’t want followers to make up their own interpretations. They recognized that writing could be more than a record of speech. According to Parkes, they elevated the status of the written word:

“Members of the Christian communities in the West developed a keen sense of the role played by the written word in preserving and fostering orthodox tradition handed down by the Church, and in transmitting that heritage to new generations.” (20)

Parkes explains how Irish and Anglo Saxon scribes developed practices that generally improved readability and comprehension of written texts.

“The principal contribution of the insular scribes was that they established the rudiments of the grammar of legibility in relation to the new scripts as well as the old, and transmitted it to later generations of scribes for further refinement and development.” (29)

This ‘grammar of legibility’ included radical innovations such as putting space between letters and words. Hence, in my crude example above, you would get something more like this:

when I talk about writing with workshop participants they always want to know when to use commas or semicolons they ask andy what are the rules I tell them to take a step back and think about the big picture why punctuation what is it for how does it function these so called rules make much more sense if you know a little something about the history and evolution of the marks we call punctuation

Putting space between words was a huge leap forward. It’s so important that writing coach Roy Peter Clark tells students to think of white space as a form of punctuation. In his most recent book, Murder Your Darlings And Other Gentle Writing Advice from Aristotle to Zinsser, Clark writes:

“If the period is a stop sign for the sentence, white space does the same work for the paragraph. The white space is a visual form of ventilation of the text. It invites the reader in, sending the message that you can glide—rather than struggle—through a report.” (249)

Let’s Talk About Marks

Punctuation as we know it is a set of symbols. Those symbols are marks that mean something. Before we get into questions of standard usage (a much better way of describing so-called ‘rules’), we should talk about marks.

What is a mark?

A period is an example of a mark. The mark is a little dot that we put at the end of certain types of sentences.

A question ‘mark’ is also a symbol, and we use it at the end of a different type of sentence.

Consider once again my crude example: How would these two marks help with legibility? With comprehension and readability?

An obvious answer is that periods and question marks would signal the end of a sentence. Let’s see:

when I talk about writing with workshop participants they always want to know when to use commas or semicolons. they ask andy what are the rules? I tell them to take a step back and think about the big picture. why punctuation? what is it for? how does it function? the so called rules make much more sense if you know a little something about the history and evolution of the marks we call punctuation.

Can you feel the frustration melting away? The same unreadable prose at the beginning of this post suddenly starts to look familiar. It’s nice, right?

If we can use periods and question marks to make the writing more readable, what other marks do we have at our disposal:

, the comma

; the semicolon

: the colon

“” quotation marks

() parentheses

– the hyphen

— the dash

[] brackets

* the asterisk

/ the forward slash

\ the backward slash

• the bullet point

And many, many more. Take a look at your keyboard. What do you see? If you use Word, take a stroll through the Insert > Symbol menu for even more marks.

We can even make marks out of marks. You know, the way three little dots make an ellipses …

Some marks employed by scribes fell out of use over time. The most common marks today only became  standardized with the advent of the printing press. Before then, personal preference and even handwriting style played a much bigger role.

You’re Ready to Edit

If you struggle with punctuation, focus on the marks that end sentences. Remember how much easier it was to read my example when the sentences were isolated? If you get that down, you’re heading in the right direction.

Keep your eyes on the prize. For business communications, punctuation should improve readability. That’s the primary function. It should be helpful, first and foremost.

What about Commas?

Commas began as a mark that indicates a pause. There was a time when the placement of pauses was generally accepted as a standard among orators. There were ‘best practices.’ But we’re talking about a time in history when most people couldn’t read. If you learned to read, you also learned the tricks for inserting pauses. (And there was still disagreement.)

Commas are a mark that people get very anxious about, in my experience. If that describes you, just remember: The comma is an invention.

Pauses in speech are subjective in nature, so a technical language was invented to produce ‘rules’ for standard usage in writing. Of course the rules vary depending on who you ask and what style guide you prefer.

I think we can all agree that commas help when it comes reading  long sentences. Here’s what my example looks like with commas:

when I talk about writing with workshop participants, they always want to know when to use commas or semicolons. they ask, andy what are the rules? I tell them to take a step back and think about the big picture. why punctuation? what is it for? how does it function? the so called rules make much more sense if you know a little something about the history and evolution of the marks we call punctuation.

Compare that with previous examples.

Another innovation is the capital letter to indicate the start of a sentence.

When I talk about writing with workshop participants, they always want to know when to use commas or semicolons. They ask, andy what are the rules? I tell them to take a step back and think about the big picture. Why punctuation? What is it for? How does it function? The so called rules make much more sense if you know a little something about the history and evolution of the marks we call punctuation.

Quotations marks are another innovation that signal direct speech. According to Parkes, scribes would indent quotes. We still do that today, but we also have the marks for inline text.

When I talk about writing with workshop participants, they always want to know when to use commas or semicolons. They ask, “andy what are the rules?” I tell them to take a step back and think about the big picture. Why punctuation? What is it for? How does it function? The so called rules make much more sense if you know a little something about the history and evolution of the marks we call punctuation.

What other marks would help make this passage in line with contemporary sensibilities?

The Takeaway!

Punctuation marks have a purpose. They have many purposes, in fact. But those purposes are neither universal nor fixed.

Here’s some advice for when you’re editing a work and worried about whether the punctuation is correct:

  • Set aside ‘rules’ for a moment.
  • Ask yourself if it’s clear where sentences begin and end.
  • Ask yourself whether long the sentences lack internal punctuation. If so, are there instances where commas could/should go?
  • Consult a punctuation nerd for guidance on standard and practical usage if you’re still not sure what to do.

Further Reading

The Glamour of Grammar by Roy Peter Clark

Punctuation: Art, Politics, Play by Jennifer DeVere Brody





For Tongue-Tied Lovers, a Lesson in Writing a Valentine’s Day Message

For Tongue-Tied Lovers, a Lesson in Writing a Valentine’s Day Message

William Butler Yeats wrote one of my favorite love poems of all time. It’s called “A Drinking Song,” and it’s only six lines long:

Wine comes in at the mouth
And love comes in at the eye;
That’s all we shall know for truth
Before we grow old and die.
I lift the glass to my mouth,
I look at you, and I sigh.

Yeats had a complicated love life, to put it mildly. For a long time, he pined for Maude Gonne, whose feelings were not mutual. They were ‘just friends,’ so to speak. Time passed. Yeats accepted that it was not meant to be.

So, he asked Gonne’s daughter to marry him. She declined.

Write your own meditation on love

You don’t need a dramatic love life to write something lovely. And you don’t need a Nobel Prize to compose something special for a special someone. (It doesn’t have to be a poem.)

With Valentine’s Day soon upon us, I thought I’d share some strategies for writing your own meditation on love, something to share with a person who means a lot to you.

Before the how, here’s the why:

Flowers fade. Chocolates melt. Conversations over dinner at too-crowded and too-loud restaurants are soon forgotten. Writing down your feelings is expresses how much you care. It’s a gesture that lasts.

Generate raw material with these writing exercises

“You like potato and I like potahto.
You like tomato, and I like tomahto;
Potato, potahto, tomato, tomahto!
Let’s call the whole thing off”

When Fred Astaire and Ginger Rogers sing this famous duet in “Shall We Dance”, they rely on ‘contrast’ to formally introduce their tongue-in-cheek arguments for breaking up or staying together.

Contrast is a reliable, well-worn rhetorical strategy that gets as much utility in politics and stand-up comedy as poetry. Dogs and cats. Mars and Venus. Liberals and Conservatives. You and I. Where is the contrast? What are the distinctions?

You need raw material to write a love note. Exploring contrast and complements is one method for getting started.

  • Start with an ‘I’ statement, followed by a ‘You’ statement. Do this as a writing exercise and generate more material than you need.

Be serious and silly. Be literal and figurative. Work in a few ‘We’ statements where you can. Flip the order and go from “You” statement to “I” statement.


  • I never eat breakfast. You never miss a meal.
  • I pass the ball. You shoot and score.
  • I like TV. You like to read.
  • I am loud. You are quiet.
  • I am impulsive. You are patient.
  • I make the bed. We mess it up again.

Finish this statement: My feelings for you are like …

Similes are an underrated writing device in personal and business communication. Poems make use of them all the time. Give yourself permission to write like a poet by completing this writing exercise.

  • First, make a new document with two columns. Or take a piece a paper and draw a line down the middle.
  • In one column, write every word you associate with love.
  • In the other, make a list of words, objects, images and memories that you associate with person with whom you’ll share this meditation.
  • Drawing from your list, finish this statement: My feelings for you are like …
  • Spend five minutes writing about why the simile is true.

An (Unedited) Example

My feelings for you are like a road trip to the beach. The destination is a given, but there are always suprises along the way. They’re like a road trip to the beach because road trips are relaxing. I like spending time alone with you. I’m thinking of a specific beach, where the weather is warm. I have warm feelings for you. Ocean waves are powerful. My feelings for you are powerful. They’re like ocean waves. My feelings for you are like being on a beach at night.

Is this bad? Yes, it’s bad. It’s raw material. It’s going to be bad.

It doesn’t matter if you’re writing a Valentine’s Day message or a 40-page report. A first draft is  generally not the last draft.

So how do you get from rather uninspiring raw material to a finished text?

You rewrite and revise. Then you rewrite and revise again.

This is what a poem looks like after it has been revised a dozen or more times:

Sommelier of the dark sea,
pass the drink to me –
I tilt the heavy bottle,
lift its sand-skirted

bottom to the moon,
drain its delightful contents,
lick my wet lips, swoon.

(Can you feel me channeling Yeats here?)

Hints for composing your Valentine’s Day message

It’s time to turn your raw material into a polished meditation. Here’s some advice to consider as you revise:

 Set some (arbitrary) limits. Write a message or a poem that’s no more or less than 10 lines. Or 4 lines. Or two lines. Whatever you decide, constraints help you shape the text. If you don’t like the shape later, you can revise.

 Address the person directly. Since a particular someone prompted you to write, why not make it explicit? Try opening your message with “To XXX.”

What to avoid / Signs of a half-baked love message

  • Avoid clichés.
  • Avoid sentimentality.
  • Avoid turning your subject into an object. People aren’t landscapes. They aren’t sculptures in a garden or dolls, etc.
  • Avoid phrases that would sound troubling if a stranger overheard them: “I love you more than life itself” or “I’d die without your love.”


A Lesson on the Physicality of Editing

Why Cage Your Inner Editor?

I am constantly surprised by professionals who are tentative about editing someone else’s work, particularly when it’s their job to make the communication as effective as possible. For a long time, I attributed it entirely to group dynamics, the idea being that no one wants to step on anyone’s toes.

But recently I’ve come to think there’s a much simpler explanation. Most people have never been shown how to edit someone else’s work. I mean, physically walked through the process. Most of what passes for writing education is the dissemination of rules, principles and best practices. But there’s a constant gap between knowing what to do and knowing how to do it.

It’s why reading books about editing won’t make you a good editor. Until you perform editing tasks, you only have knowledge and not experience. I started thinking about where I learned to edit, who modeled it for me and if I could pass that knowledge along? I had several formative experiences, including:

  • One of my early composition teachers wrote extensive feedback on every assignment. She would cross out entire sections of an essay, correct grammatical errors, ask questions in the margins, write long explanations for her edits. It was a peek into the mind at work during the editing process.
  • Writing and workshopping poetry, I learned not to take criticism personally, to hear other perspectives, concentrate on concision, and weigh the meaning and context of every word. I also learned that the writing is never done. You can always make more changes, so at some point you just have to cut it off.
  • Early in my career, I had mentorship from great newspaper and publishing professionals. Editing and rewriting are (or used to be) taken for granted in newsrooms. You might argue over an edit, but you didn’t expect not to be edited.
  • Working directly on layouts in desktop publishing programs, I confronted the process of editing in the most visceral way. One of my tasks as a young editor was to cut the overflow copy after it was laid out by the designer. When you see exactly how much space you have and know exactly how much has to be cut, you start whacking away.

The last item strikes me as one of the most important. The actual physicality of deleting whole chunks of text and then rewriting other chunks, making decisions about what was most important and what could go – that is an experience most people don’t get.

A Simple, Surprisingly Powerful Editing Exercise

Set aside the politics around editing your co-workers’ writing for a moment. What stops you from rewriting a 1,000-word memo when it would be better off as a 250-word memo? If my theory is correct, that most people have never had the physical sensation of editing for length and organization, then what can we do about it?

Toward that end, I crafted an exercise several years ago to use in my corporate training workshops. It starts with a rambling 800-word ‘letter’ about my travels to another country. I wrote it in a sitting, without stopping, so it would be deliberately associative.

The task for workshop participants is to reduce the letter from its original length to 1) 400 words, 2) 50 words and 3) 140 characters.

Set up this way, participants have no choice but to start crossing out huge chunks of text, including sections that might have been well-written and filled with interesting details.

It also forces participants to make choices about what is most important in the letter. They have to decide on an assumed audience.

In discussions afterward, we compare the results and talk about the choices they made. But when participants also talk about the experience they had, how good it feels to take control of the text, to delete and rearrange with confidence – then I know it’s a success. MW

Start Your Next Story with the “I am here” Pattern

Sometimes writers overthink story beginnings, when the more important thing is to simply start writing (because you can always revise).

The following sentence pattern is an easy way to start any story and get you writing.


I use patterns like this one because they’re generative. That is, once you write where you are, the next sentences beg you to say what you’re doing, what you see and hear, and so on.

Here’s an example, from right this moment:

I am at home, sitting at my office desk. It’s nearing midnight. My wife, who took on a cold two days ago, sleeps fitfully across the hall.

This is already the bare bones of a story. If I change the point of view to third person (and do some light revising), I have material that might be the beginning of a fictional short story:

He sat at the desk in his home office, the clock nearing midnight. His wife, who took on a cold two days ago, slept fitfully across the hall. Coughing and sniffling, she woke herself up twice, and both times called him to come to bed.

I don’t know who these characters are yet, but I’m on my way to finding out, all because I started with a simple sentence pattern.

It also works for nonfiction

The “I am here” pattern works for nonfiction too, maybe even more so. After attending a conference for a magazine client, I started the recap like this:

“I’m in Las Vegas at the PPAI Expo, standing in front of a makeshift stage. The executive chef of a well-known meat company is demonstrating how to grill the perfect steak. First he sprays a nice cut with oil, then shakes seasoning from a canister until the top is coated. Then he throws the meat onto a preheated electric grill (manufactured by another well-known company). After a moment, the smell of grilled steak drifts from the stage to my nostrils, and I am suddenly hungry.”

Let me break this down even more

I started forming this process one Friday in a bookstore. I was flipping through a food magazine, and one of the stories started with the “I am _________” pattern.

I went to a coffee shop to write. These are what my notes looked like:

  • I’m in a coffee shop in Del Ray.
  • I ordered a Colombian pour over coffee
  • I’m at a coffee shop in Alexandria, Va., sitting at a table made of reclaimed wood and trying to guess how many other freelancers are here with their laptops and phones.
  • I’m at a coffee shop in Alexandria, Va., sitting with my laptop at a table made of reclaimed wood and waiting for my order to be ready.
  • I’m at M.E. Swings, a coffee shop in Alexandria, Va., sitting with my laptop at a table made of reclaimed wood and waiting for my order. Swing’s is authentically hipster (a ) in that it is truly old and new at the same time. The brand is XXX years old, founded in XXX by XXX . But there’s nothing about an old commercial roaster. It’s the brand that’s authentic. The name, the values it stands for, etc.

In five short iterations, I found a center, a real scene, at least enough of one to get a story started at least.

Notice that each iteration gets progressively more detailed, and some iterations rely on different details than others. So the sentence construction is really just a launching point. The real exercise is to start noticing things. This is a good practical way to do it. (If you are not practicing but actually working on an assignment, this means taking great notes.) MW

Writing Exercise

Where are you right now?

Write it down like this:

“I am _____________”

Keep writing.

A Writing Lesson in Sentence Length

Maybe you never knew this, or maybe you learned it a long time ago and forgot:

Good writers are good at varying the lengths of their sentences.

Sentence length contributes to style, which contributes to meaning and also makes writing more interesting to read.

Here’s a quick example. Which is more interesting to read?

John left the house. He walked to his car. He turned the car on. He drove down the street. He got on the highway. He cruised at 60 mph. He arrived at work. It was 20 minutes later.

John left the house. He walked to the car, turned it on and drove down the street to the highway. He cruised at 60 mph all the way to work. He arrived 20 minutes later.

The content of the sentences is almost exactly the same, but the latter bookends two longer sentences with two shorter sentences, illustrating a simple concept:

Variety in sentence-length helps move writing along (even if the content is bleh).

What I love about this or any example is that the combinations are nearly infinite. Here’s a different version:

John left the house. He walked to his car and, after turning it on, drove down the street to the highway, on which he cruised at 60mph all the way to work. He arrived 20 minutes later.

Now there are only three sentences instead of four, and the long one is still bookended by two shorter ones.

Also, combining all the ‘driving’ action into the same sentence has an interesting effect, in that the sentence structure now mimics the movement of the scene. It makes more “sense” to start a new sentence at the same time the driving action ends and a new action begins — John arrives at work.

(If you ever wonder what writers do, this is it. We spend a lot of time playing with different combinations to get just the right effect.)

You can do this too

I want you to start mixing long and short sentences in your writing. To do it well, you’ll need to master two fundamental skills:

  • Writing short sentences
  • Writing long sentences

To help, I recommend reading these two books:

  • Write Short: Word Craft for Fast Times by Roy Peter Clark illustrates how to generate powerful rhetoric in as few words as possible.
  • Building Great Sentences: How to Write the Kinds of Sentences You Love to Read by Brooks Landon is a great introduction to the benefits and techniques behind writing long sentences.

Both are filled with really good, practical tips, exercises and rationales for writing different kinds of sentences. Even if you only spend a short time each week practicing these techniques, the rewards vastly outweigh the investment. You’ll be on your way to developing a unique voice, rooted in the development of a personal style, whose writing projects real authority, vastly superior to the bland, fake-positive, message-driven, inauthentic style that is the default of less talented copywriters, content marketers and bloggers (they know who they are).

In other words, keep at it. Before long, you’ll be a pro.