[Tipster] The Pesky, Puzzling Punctuation Mark

The semicolon is a mystery to many; just ask my friend. 

She’s a paralegal at a snazzy Chicago law firm.

One of her primary functions is to review legal briefs written by the attorneys in her office. 

One lawyer’s briefs are bedazzled with semicolons, like a Christmas tree decorated by a 3-year-old.

“He places them in his briefs like ornaments,” she says.

Where a comma is necessary, he places a semicolon; where a period is perfect, he places a semicolon; where a colon is correct, he places a semicolon. 

“He must think they jazz up his briefs,” she says. “Or maybe they make him feel like a sophisticated writer.”

But really, they signal the opposite. Misuse makes your writing look amateurish.

The Soft Stop vs. the Hard Stop 

I’m one of those people who geeks out over punctuation, and how using a semicolon instead of a period, for instance, can actually change the meaning or flow of your writing.

Punctuation can be used strategically. And it ought to be if you are mastering the craft of writing.

But first you need to know how to use it correctly.

And the semicolon is one of those pesky punctuation marks that puzzles writers.

I like thinking of the semicolon as a weak period. A period, of course, is used to signal the end of a sentence. It’s a hard stop. 

Semicolons are stops as well. But softer stops. They are stronger than a comma. But softer than a period.

They are used to link two closely related ideas, which on their own stand as independent clauses (independent clauses, if you don’t know, form a complete sentence).

And that’s the catch: the clauses must be independent. You can’t have an independent clause and dependent clause separated by a semicolon. (That’s the work of an emdash, a comma, or maybe a colon). 

“Will a Semicolon Work Here?”

Here’s a helpful question about when to use a semicolon:

Can I replace the semicolon with the period and two complete sentences would stand?

Sometimes the two independent clauses are opposing ideas. Using a semi-colon signals you want the reader to take in the two ideas together. 

Often the second independent clause is a closely related logical statement. Check out my opening statement.

There are other uses for semicolons, like in serial lists, or when linking two independent clauses with a conjunctive adverb; however, I won’t get into those instances today.

Start today by mastering the semi-colon that separates two independent clauses.

Resist the temptation to use it too much.

And use it strategically: create a deliberate pause between two linked ideas.

You can do it!

[Tipster] Writers Have Words Only

Melissa and I just attended a terrific conference called STORY in Nashville.

We presented a breakout session called "The 5 Elements of Putting Your Story to Words."

Many of the attendees were brand marketers, designers, and creators of all kinds of digital products, and other goods and services.

A few were writers.

The speakers were fantastic, the videos and visuals in the presentations were breathtaking.

Every presenter trumpeted the power of story. To change one's life. And to change the world.

On one level, it's fully true that you, as a writer, are in the story-telling business.

If you can't tell a good story, you won't hold your reader's attention for more than a page or two.

No one wants to read information only.

It's Always about Showing, Not Telling

But writers have a herculean job to do when story telling.

It's relatively easy to say as a brand or as a marketer, "We tell stories for our products and services."

They have more tools - images, video, and audio (voice, music, etc.) - to story-tell.

You, as a writer, do not.

You have words only.

So you can't "tell a story." You'll bore your reader.

You're not a designer.

You don't have an image to show your readers. You have to paint an image with your words.

You're not a videographer.

You can't show a close-up of the roll of the eyes or facial anger.

You can't just write, "She was angry."

You must show that she is angry ... using words:

"Her lips trembled ever so slightly, and then she cupped her hand and slapped him on the back of the head."

You have no audio.

So, you have to write words in such a way that the reader hears the crickets that interrupt the silence.

You have words only. And words alone.

Your Last Ten Pages

Here's a quick assignment. Review the last ten pages that you wrote:

1. Are you telling what happened? Or are you showing what happened?

2. Do you have clear scenes that paint a picture for the imagination of your reader?

3. If you are writing nonfiction, are you merely burping out information? Or are you layering your writing with anecdotes and stories and illustrations that show the point you want to make.

If your writing sucks, it sucks because you don't show. You tell.

Any writer can learn to show. Showing is a skill. It's a skill you can learn.

We all can get better at showing.

Writers don't tell stories. Writers show stories.

Now, buckle up and show!

[Tipster] No Room for Writing Compromises


On Monday, I hit a milestone. I wasn’t expecting to.

There I was: sweat dripping from my face, mid-movement of a tricep extension.

And I heard my coach congratulate me, “It’s your 150th class!”

A year ago, I joined Orange Theory, a boutique fitness studio franchise.

It was pricey.

But like many others who lost a bit of themselves during Covid, I was desperate to regain a modicum on control of my life.

I was willing to pay extra for a fitness partner.

My research told me that, through a variety of methods, Orange Theory consistently helps its members make progress in their fitness journeys.

They do it through tough love. You pay extra if you sign up for a class and don’t show. (Ouch! I’ve only made that mistake once.)

They also do it through goal setting and celebration.

Coaches learn your name and cheer you on during class. Their quarterly fitness challenges push you to achieve more than you thought possible. And the entire class celebrates your fitness benchmarks, whether it’s your 150th class or 3000th.

Working out still isn’t easy, since I’ve gone orange. But I don’t compromise my workouts. 

I feel in control of my health.

The Compromised Writing Life

One of the biggest challenges for writers is not compromising the time you say you want to devote to writing.

You want to improve your writing. You want to complete a book or an article.

You put it on your calendar. Before you go to bed you vow to write first thing in the morning.

Some of you are disciplined (congratulations!). But many of you, like me, compromise your writing time.

You’re not in the mood.

You sleep in. 

You do work that “feels” more pressing.

You convince yourself you’ll do it later.

Simply, you excuse yourself. Because writing is hard. And excuses are easy.

Compromise vs. Community

Doing hard stuff solo isn’t impossible. But often is more difficult.

Last week for our podcast, we interviewed an author who wanted to complete a novel. She’s a trained writer, editor, and literary critic.

She knows how to write.

But that didn’t make writing easier for her. She needed accountability.

She put an ad in Craigslist, seeking serious writers who also wanted to complete a writing project and who would be willing to engage in mutual feedback.

They met once a month. And before each meeting, she completed a chunk of writing for her peers to review. 

That’s how she completed her novel.

That’s accountability at its best.

And it’s why Dave and I have decided that Roadtrippers, our online learning community, will return to weekly sessions.

Our Roadtrippers told us they missed the weekly connection with other writers—who often are struggling with the same things they are: like rejection, finding time to write, or feeling stuck with an idea.

They also mentioned that weekly check-ins and goal setting kept their writing momentum going.


[Tipster] It's Time to Complete Your First Rough Draft

A friend sent me a great quote from Twitter the other day:

"I don't know who needs to hear this, but a first draft does not need to be good - it needs to be written."

The quote comes from Emily Bremer, someone I've never heard of before. Apparently, she is a Notre Dame law school professor.

But she is dead on.

We talk endlessly (and sometimes drearily) at Journey Sixty6 about burping out that first draft, version 1.0, or whatever you want to call it.

There are at least three reasons that I procrastinate in completing my first drafts:

1. I am not passionate about the idea anymore.

Writing is such a long slog. Over time, ideas lose their hold over my imagination.

I've been working on an idea for a book for several years. Recently, I completed a first draft of the first chapter.

Suddenly, I realized, "I don't even like this idea anymore."

My procrastination was in part due to a slow leak of passion for the idea.

It wasn't until I completed the thesis chapter that I discovered that I don't have the energy or passion to complete the project.

2. I keep going back to rework that which I've already written.

A first draft is simply that. A first draft.

And a first draft will likely be the first of, well, many, many drafts.

But I tend to be drawn back to the last section that I just wrote.

I move sentences around, wrestle with stronger verbs and nouns, and add supporting stories to my initial ideas.

That is an important function of writing.

In fact, it's essential to writing something worthy of publication.

But it is a stall tactic while working on that first rough draft.

There will be time for editing.

Just keep laying down new sentences.

3. My priorities have changed.

I say that I want to write. But in reality, I want "to have written." I want the writing to be over.

I want the accolades that come from having written.

Consequently, I make time for other priorities in my life (like fly fishing), but I don't give the same focus to my writing.

Perhaps my priority was completing the first rough draft, but now, because of the vicissitudes of life, my priorities have shifted.

That's okay, but the first draft is still the first significant milestone to get to the end of the writing journey.

So, let's buckle up and write that first draft!

[Tipster] The Essence of Storytelling: Show Don't Tell

If I wasn’t speeding down the expressway already late for my appointment, I would have jotted down this scene from a podcast I was listening to. 
It would make for a great detail in a novel.
But I had to commit it to memory, which wasn’t difficult. (You’ll see why.)
The podcast was a true story of a college-aged girl in an abusive relationship with a man 20 years her senior.
After an evening of verbal attacks and gaslighting, she stopped by the grocery store for an XL box of Fruity Pebbles and a gallon of nonfat milk.
When she got home, she pulled out her plastic popcorn bucket (the reusable kind from the movie theater). She poured into it the entire box of Fruity Pebbles.
 And drowned it in milk.
She sat cross-legged on the floor and began eating it, spoon by spoon, even as the Fruity Pebbles dissolved into mush. 
As I listened to her story, I saw her despair—I felt her despair!—with each soggy spoonful.
Writing for the Senses
You’ve likely heard the writing advice “show don’t tell.” 
The idea is that you use sensory details to bring your reader into the scene—so they can experience it. 
As Russian writer Anton Chekhov famously said, “Don’t tell me the moon is shining; show me the glint of light on broken glass.”
Imagine if in the above story, the narrator simply said, “I was so depressed. I didn’t know how I was going to escape the relationship.”
That’s a forgettable statement. 
And I likely would have forgotten this particular podcast episode. 
But I didn’t forget it—because I felt something for the character in that moment. I imagined the despair that might drive me to eat a popcorn bucket-sized serving of Fruity Pebbles. 
That’s the essence of great storytelling. 
It brings the reader into a sensory experience that lingers after the story is put down.
Can a Director Picture It?
Here is one way to begin to evaluate if your storytelling needs more showing:
Imagine giving your scene to a TV show director.
Would she be able to create the scene the way you imagine it in your mind? 
Does she have enough details to direct the characters to act a certain way—to do certain things? 
Does she have enough details to create a set?
Let’s go back to the original story from the podcast.
Imagine if I simply gave a director a story that said, “When she returned to her apartment, she was depressed. After four years she hadn’t left her abuser and still didn’t see a way out.”
The director could create a thousand different scenes to show the despair and depression. 
The onus is on the director to find the best way to depict it. And it likely wouldn’t match what you had in mind. 

[Tipster] The Use of Foreshadowing in Your Writing

The single biggest challenge in almost any form of writing is attention:

How do you sustain the attention of your reader?

There's an old line:

"When there's no more tension in a story, the story is over, whether the storyteller is done telling the story. Or not."

Readers simply stop reading. They put down the book and turn on Netflix.

The art of writing is the art of creating, resolving, and recreating tension. Essentially, it's the art of writing a story.

Well-told stories arrest and keep the attention of their readers.

It's the "keeping" part that is so challenging ... for all writers.

Foreshadowing Technique

There are many ways to create and sustain tension in your storytelling.

One is "foreshadowing."

It means "a warning or indication of (a future event)."

In short, as you write a scene or tell a story, you signal that something (often ominous) is going to happen.

This doesn't give away the cookies.

In fact, it raises tension. It makes the reader lean forward in her chair.

The reader now knows that something big is going to happen.

Catherine's Coup

In the spot in the biography that I'm (still reading) of Catherine the Great, she is now in her early thirties.

She is the wife of Peter III, the grandson of Peter the Great.

Young Peter has just ascended to power because his aunt (Russian Empress Elizabeth) basically handed him power before she died.

But Peter (now also in his early thirties) was an insolent, petty, "small man" who preferred to play "war" with his guards. Right before he was overthrown by Catherine, he renounced his Orthodox faith and embraced Lutheranism.

He really wanted to be Prussian (like his father), not Russian (like his mother).

You can't imagine what a slap in the face that was to the Russian elite and, especially, the Russian Orthodox Church.

Within 186 days of Peter's ascent to power, Catherine (Peter's wife) overthrows him. She had curried favor with some of the Imperial Guards and others.

Here's the foreshadowing in the text. There is a party a few days before the coup by Catherine:

"On June 19, an opera was performed during which Peter played his violin in the court orchestra. Catherine was invited and came from Peterhof. This was the last time husband and wife were to see each other."

See that last phrase?

That is foreshadowing.

It comes at the beginning of the scene in which Catherine overthrows Peter.

It signals that Peter dies in the coup.

Some Takeaways

1. Raising and sustaining tension in your writing is the ONLY way to keep a reader's attention.

2. There are many storytelling techniques to do that.

3. Foreshadowing is one technique to create tension and signal what comes next.

See if you can foreshadow some event in your memoir, fiction, or even nonfiction writing.

You can do it!

Now, buckle up and write.

[Tipster] Dig Deeper for Your Story Hook

“Melissa, I need you to rewrite this article. The hook is a cliché.”
My editor at Flea Market Style magazine served me one of the most valuable writing lessons. 
With a good eight hours already invested in the article, I didn’t want to rewrite it. 
But she was right. The opening was predictable and therefore forgettable. 
You have one chance to grip the reader, and I had failed.
If you read shelter magazines (or watch any HGTV show, for that matter), you’ll know the storyline—the one I launched my article with: 
A young couple finds a run-down old house and, with passion and creativity, brings it back to life.
Like I said, it was a yawner.
The Buried Lead
I needed a new hook, a better angle. So, I went back to my homeowner interview transcript. 
I scanned the highlighted sections—the quotes and stories that were idiosyncratic, funny, moving, or insightful.
And there it was: my lead. Buried deep in the transcript.
It was a story about how the couple visited an estate sale and found a bundle of love letters penned by a WWII soldier to his love back home. 
They bought the stack and began reading them one by one, slowly and only together. When I interviewed them, they weren’t even a quarter of the way through the stack.
I lingered on that story. 
It was the most memorable part of the interview. But how could I stitch it into a story about a couple and a house and a makeover?
I probably took a few walks or did some laundry before the opening crystalized. 
Their Love Letters
The story wasn’t about the home. It was about the people in the home, Ky and Phoebe.
They were romantics, and their home was their own romance story, or love letter.
So, I started the story with the love letters, and here’s how I transitioned to their home (because the story was supposed to be about their home):
“When the couple began renovating their 1920 Everett, Washington bungalow, they became immersed in yet another stranger’s love story. A simple message they found written on trim in the attic reads: ‘Bud Agnew, I always will love.’ 
“The couple wasted no time tracking down the story of Bud… Stumbling upon stories like these inspires Phoebe …
“In some ways, Phoebe and Ky have been writing their own love story for the old house, which had been inhabited by squatters and animals.”
Trust Your Gut
I wish I would have trusted my gut. 
I knew that the love letters story was the lead, but I defaulted to the easy home-makeover cliché. Clichés are convenient.
Yes, it was tricky to find a way from the love letters to the house. It demanded thinking creatively. I had to mine for the metanarrative that would tie...

[Tipster] The Good Stuff

Ernest Hemingway was a wretched soul.

But he remains one of America's greatest fiction writers.

I recently read a profile of Hemingway, which was published in the New Yorker in 1950.

The profile is titled "How Do You Like It Now, Gentlemen? The moods of Ernest Hemingway."

Hemingway makes a profound statement about writing that we ignore at our own writing peril.

The Cutting Room Document

Whenever I'm writing longform (more than 1,500 words), I create a Word document called "Garbage."

This is in addition to the Word document that contains my writing.

I do this as a reminder that not everything that I write should make it to the final draft.

So as I write, I'm constantly moving stories, quotes, and ideas from one document to the other.

Obviously, all the ideas start in the Word document in which I'm laying down my first draft.

But as I edit, I don't just adjust sentences and move ideas around. I also cut big chunks.

This is a heartbreaking, thankless chore.

But it's foundational to ending up with a final version that makes you feel your writing is complete.

It's the Good Stuff that Needs to Go

In the profile, the writer (Lillian Ross) describes the scene of one of her conversations with him:

His briefcase was lying open on a chair near the desk, and the manuscript pages were protruding from it; someone seemed to have stuffed them into the briefcase without much care. Hemingway told me that he had been cutting the manuscript. “The test of a book is how much good stuff you can throw away,” he said.

Note his phrase - "how much good stuff you can throw away."

Other writers have written about this same, dreary pruning of your own writing: "Kill your darlings."

It's the "good stuff" that needs to be strangled.

It's good, not great.

How do you know which is good and which is great?

What an impossible question! Here's three ideas, however:

1. You send your writing to a reader, and she says, "I like it."

That isn't much of a mandate. "Like" is emotionless.

If she only liked it, most likely you haven't cut enough of the "good stuff."

The better response would be if she started telling you a story about her own life: "That reminds me of a time when ..."

Maybe she raised her eyebrow as she read the piece.

You want your writing to move people.

2. You keep a chunk (perhaps a story) because you need your writing to be a certain length.

This is death.

Maybe you resist cutting a story because you have no other stories in that section. It needs at least one anecdote or scene, you think.

But it isn't gripping in any sense.

Cut it. Always move the average story to your "Garbage" document.

3. You write a lot.

The only way to learn what to cut is to keep writing. Truly.

The more you write, the more you start to sense what works and what doesn't.

Now, buckle up and kill that darling!

[Tipster] Procrastinate Your Way Out of a Writing Block

If I’m scrubbing a toilet at 2:30 on a Wednesday afternoon, I’m likely procrastinating. 
I’m an expert procrastinator, especially when it comes to writing. 
I love-hate writing like I love-hate running.
It takes more energy lacing my sneakers than it does to actually run my route. My dread lifts as I move forward – one breathless step at a time.
And you can’t buy the endorphin rush and pride that a run rewards you with.
Still sometimes I never make it to my sneakers. I say, “Tomorrow.”
What Moves Your Writing Forward
It’s the same with writing. Writing never feels easy. At least not for me. 
Even writing Tipster on occasion sends me to the laundry pile. 
Yes, I’ve fooled myself into believing that matching socks—most of which lost its pair somewhere between the feet and the dryer—is less painful than writing.  
But nothing feels quite so satisfying as a finished writing project. Certainly, it’s more satisfying than matching socks, or scrubbing a toilet.
On the other hand, procrastination can be a gift. It can actually move your writing forward.
Hear me out.
Procrastination: A Dose of Dopamine
When I procrastinate, it’s usually because my thinking on a topic is too clunky (I haven’t winnowed my idea enough) or too thin (I haven’t done enough research or thinking on the topic).
I’m usually spitting out ideas that don’t stick. Or writing and deleting the opening sentence of a paragraph 18 times.
When I turn to an activity other than writing, I often break out of the block. 
There’s science to it—and why you’ve probably noticed you do some of your best thinking in the shower. 
Neuroscientists who have researched creativity found that we are more creative when more dopamine (the chemical responsible for relaxation) is released in our systems.
Creativity Surges
Here’s how it works. A shower relaxes you, you’re hit with some dopamine, and with it your creativity surges.
The same thing happens when I step away from my writing and take a walk down the block, drive to Starbucks, or even fold laundry and clean the toilet.
And there’s another thing that happens when you turn from writing to mindless activity.
Think about those days when you type, delete, type delete. 
And at the end of a two-hour writing session, you have one crummy paragraph.
Then you cook dinner or weed the garden, and suddenly your ideas find form. Scientists call this mindless period the “incubation period.” 
Your subconscious mind has been grinding all day, and once you let your mind wander, new ideas surface to your consciousness.
So do it: Procrastinate to write more creatively and freely. 
I’m giving you permission today.

[Tipster] It's Time Once Again to Shorten Your Sentences

A long, ugly sentence lays on your page like I lay on the couch after one too many slices of Chicago-style, stuffed pizza.

I feel like taking a nap.

And so will your reader if you don't shorten your sentences.

I've written on this topic before: If you want to learn to write well, put your sentences on a diet.

Here are 5 good reasons:

1. Short sentences give you control over your meaning.

The moment you start to shorten your sentences, you're forced to be more specific about what you actually mean.

Short rubs your nose into the page and forces you to ask, "What is the most important element in this sentence."

And, "What do I really want to say?"

Short helps you write more crisply. More precisely.

2. Short sentences teach you how to write longer sentences.

You can always write longer sentences later, once you've mastered the short sentence.

By shortening your sentences, you learn to write better longer ones.


With a short sentence, you're back to nouns and verbs - the two most basic elements of a sentence.

You then can begin to learn how to create compound (and longer or more complex) sentences.

Short sentences gives you a strong writing foundation.

3. Short sentences help you whack unnecessary adjectives and adverbs.

This is one of the big problems with longer sentences: bloated writing.

Too many adjectives. Too many adverbs.

You should write, "The dog barked." NOT, "The dog barked loudly."

"Loudly" is a crappy adjective. Superfluous. Cut it.

And by cutting it, you've just shortened your sentence by one word.


4. Short sentences help you end your sentences more powerfully.

Yes, how you end a sentence matters.

It creates the final emotion or idea.

Does your sentence end with a dreary prepositional phrase: "The horse trotted on the pavement."

No, no, no!

Here is the better version: "On the pavement, the horse trotted."

The sentence isn't shorter, but by writing shorter sentences, you start to think about how to end your sentences.

Having "trotted" at the end creates a visual. I can see a horse trotting in my mind.

End your sentences with creative, fresh words.

5. Short sentences kill sloppy verbs.

"Death to weak verbs."

This should be your battle cry as you shorten your sentences.

The simple act of breaking one long sentence into two shorter sentences forces you to take a harder look at the verbs in each new sentence.

"The man ran slowly and then fell down, falling forward awkwardly."


"The man stumbled as he ran from the car. And then he collapsed."

Two distinct sentences. Note how the verb "collapsed" ends the second sentence.

That adds emotion and movement to the sentence.

One Final Thought

Finally, I've recommended this book before. It's a gem: Several Short Sentences about Writing

Now, buckle up and write ... crisper, shorter sentences.

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