Finding the Sentence That Breaks Reality

Why your best writing feels like nothing special

What makes a sentence so good that you have to put the book down and stare out the window? Not just clever wordplay or literary gymnastics. It takes a startling sort of presence, a total attention.

Most writers spend their entire lives chasing these sentences.

The world was so recent that many things lacked names, and in order to indicate them it was necessary to point.

Gabriel García Márquez, One Hundred Years of Solitude

So we beat on, boats against the current, borne back ceaselessly into the past.

F. Scott Fitzgerald, The Great Gatsby

Here's the thing nobody tells you about really good sentences: they often feel like nothing when you write them. Just ordinary words doing ordinary things. It's only later, reading back, that you might realize you've captured lightning. This is why poetry matters to prose writers—not because poetry is fancy, but because poetry knows that attention is sacred.

My MFA degree was in creative writing with a focus on poetry. Considering the MFA, I had two options: poetry or fiction.

My reasoning went like this: Poetry's obviously the right choice. Fiction is just stories and stuff. But if you study poetry, you get to bring all your attention to focus on the line, the phrase, the image, the feeling. Any good tale-weaver can teach storytelling, but only a true guru could teach poetry. Poetry is the purest art using the most versatile and challenging medium. Learn that, and you climb the mountaintop of self. The rest of your life will be clear.

Of course the MFA didn't quite turn out that way, and my reasoning was uninformed.

But for a span of three years I was professionally required to pay a lot of attention to "the line," to good sentences and imagery and metaphors, things like that. On a quest to unlock the really good sentence that arrives like a Greek god, fully formed and perfect from wherever sentences come from.

I think about this quest when I practice what I call the "turning a phrase" exercise, which you can find in Deep Freewriting. The exercise shows how much it matters the way something gets written. It's not as if you can write something in two different ways and it won't make a difference.

You start with a simple sentence—say, "A man walks down the street"—and you iterate on it, and you see how each new iteration reveals new facets of experience. "The empty street had its hands in its pockets as a single man walked down it." And so on.

This is the sort of thing I think is interesting about poetry, and why poetry matters to anyone trying to write a really good sentence. Not because poetry is fancy or elevated, but because poetry understands that attention is the most sacred thing.

The art of knowing that you don't know

John Keats, like it or not, gave us a term for this quality that makes certain sentences shimmer:

"negative capability," that is, when a man is capable of being in uncertainties, Mysteries, doubts, without any irritable reaching after fact and reason.

He was talking about Shakespeare, but he could have been describing the state you enter during writing—that fertile uncertainty where the best sentences emerge.

Think about Basho's most famous haiku:

The old pond

A frog jumps in—

Sound of water

It's not a clever or decorative poem. It's present. There's complete attention to a single moment. The poem is too short, too light, too quick to bother explaining or justifying itself. It presents an experience with such clarity that we feel we're there, hearing that particular splash on that particular evening centuries ago.

Writing those lines drew attention to the moment. But because writing creates a record of the journey, they also do more.

This is what I mean by a really good sentence: language that doesn't just point or describe an experience but becomes experience.

Kobayashi Issa wrote:

On a branch

floating downriver

a cricket, singing

The cricket might be doomed. The branch is heading wherever the current takes it. But the cricket sings anyway.

I can relate.

This is presence of a different order—not the stillness of meditation but the full engagement with life even (especially) when everything is in motion, uncertain, possibly catastrophic. The really good sentence can hold all things: both the cricket and the current, both the singing and the threat of catastrophe.

A really good sentence is like a cricket singing on a branch that's floating downriver. It knows it's doomed—all sentences are doomed to pass—but it sings anyway.

The sketching exercise

In Deep Freewriting, we use what I call the sketching technique—a jotty bit of writing where you just put down the main ideas. Think of it as writing out a bulleted list.

But here's the thing: when you sketch in this way, staying loose and present, you're learning to hold structure lightly, to let form emerge from attention rather than be locked into preconceived notions for something right or wrong.

Think of Jean Follain's prose poems. Take this opening:

It happens that one pronounces

a few words just for oneself

alone on this strange earth

then the small white flower

the pebble like all those that went before

the sprig of stubble

find themselves re-united

at the foot of the gate

which one opens slowly

to enter the house of clay

while chairs, table, cupboard,

blaze in a sun of glory.

The casualness is deceptive. That "It happens" creates a whole atmosphere—provisional, observant, ready for whatever might occur. This is also sketching: creating a container spacious enough for discovery. It evokes a certain altitude of perspective.

In Jesus' Son, Denis Johnson writes: "I knew every raindrop by its name." Do raindrops have names? If so, how long do they keep them? The sentence blows beyond rational thought.

Circling back

When you reread what you write, you sift through for nuggets and let everything go that is murky or frustrated. But here's the secret: sometimes the murky parts are where the really good sentences hide. They're in the mess, in the uncertain places where you're reaching for something and doing a terrible job at declaring what it is.

So circle back repeatedly. You write about something, then you return to it from a different angle, then another. It's like Cézanne painting Mont Sainte-Victoire over and over—not because he's trying to get it "right" but because each return reveals new facets of attention.

Try this: the present moment marathon

Here's an exercise combining writing with present-moment awareness:

• First phase: Write about where you are right now, maybe physically, maybe in a broader sense. Don't explain or justify. Just observe and record.

• Realignment: If you get pulled too far into one facet of your experience, return to the fundamental question as to where you are right now and ask yourself: "What do I notice now that I didn't notice before?" Keep writing without stopping.

• Return: Go back through what you wrote. Take a sentence, rewrite it seven different ways, changing something each time—tense, perspective, focus, distance.

• Put a bow on it: Return to your original observation. What do you see now that you couldn't see before? What changed during the process of observation

The point isn't to produce a masterpiece. It's to practice presence through language.

Part of the reason why freewriting is useful for writing better sentences is because it bypasses the part of you that would judge the sentence before it has a chance to exist.

The really good sentence doesn't explain the mystery. It is the mystery, made manifest in words.

So keep sketching. Keep turning phrases like you're polishing stones in a river. Keep sitting in the hot seat of not-knowing. Keep circling back to what matters. The really good sentence is out there.