Write Better Sentences

It Was the Best of Sentences, It Was the Worst of Sentences: A Writer’s Guide to Crafting Killer Sentences

6 min readJan 17, 2023

Originally published: https://chengweihu.com/write-better-sentences/

Why are we conditioned to fear writing? When we speak, it’s easy and pleasant to convey our thoughts. However, we spend more time thinking about what we want to say when we write. This extra time allows us to worry about writing and thus overcomplicate it.

What’s worse, we often have more information than we can use in our heads, and we don’t know what to leave out. Forming ideas in our heads into sentences on paper trips us up.

It Was the Best of Sentences, It Was the Worst of Sentences is a book to help us. To be more specific, it is an editor and language columnist’s guide to mastering the art of writing better sentences. The sentence is a microcosm of any written work. Understanding it means understanding the writing itself.

Author June Casagrande compiles essential grammar rules with real-world examples to demonstrate how to write effective sentences and avoid bad ones. This book offers tons of practical advice in an easy-to-digest and funny way. Here are some of my takeaways:

Why do our writings go bad? Thy Reader, Thy God.

What’s the main reason that our writing goes bad? When we speak, we can see our listeners. But when we sit down to write, someone is missing. We don’t have our readers sit in front of us. If we want to master the art of writing, we must accept the unpleasant truth: Thy Reader, Thy God.

The Reader is king, and we are their servant. We serve the Reader information. Our writing is always about the Reader, even if it’s literally something about us, like memoirs or personal essays. The most useful guiding light to help us distinguish good writing from bad: think about whether it is Reader-serving writing versus Writer-serving writing.

Avoid upside-down subordination: Don’t downplay the main character.

Subordinating conjunction relegates a clause to a lower grammatical status in the sentence. It includes words like after, although, as, because, before, if, since, than, though, unless, until, when, while, and phrases like as long as, as though, even if, even though, in order that, whether or not.

Subordinating conjunction makes the other part of the sentence more important by subordinating its own status. For example, in the sentence “Although walking through the park is good exercise, jogging is better”, we emphasize jogging by lowering the status of walking.

The troubling mistake occurs when a writer subordinates the exciting part of the sentence, which is called upside-down subordination. For example:

Bob realized he was angry after he got hit by a train and shot John in his face with the shotgun.

This sentence inadvertently takes a less intriguing piece of information (Bob was angry) and treats it as though it were more notable than the more unusual part (Bob got hit by a train and shot John). Occasionally, that might be precisely what the writer intended. But often, it’s accidental and undermines the sentence.

Comparing these sentences and we should see how subordinating conjunction can shift the focus of a reader:

Before hijacking the plane, Alice was a banker for twenty years.
After working for twenty-five years as a banker, Alice hijacked the plane.

Passive structure can be good: Use it to downplay the doer.

“Passive structure is bad, and we should always avoid it” is a common myth we need to debunk. A passive structure (passive voice) occurs when the object of an action is made the grammatical subject of a sentence. For example, “The cake is bought by Cathy.” emphasizes more on the cake while “Cathy bought the cake” doesn’t.

Similar to upside-down subordinating conjunction, a passive structure is terrible when we put the wrong thing under the spotlight. “Pasta is loved by Sam” might be a bad choice compared to “Sam loves pasta” because the former focuses too much on just pasta and neglects Sam. Similarly, “The compliments were appreciated by Tom” might not work well when we focus on Tom.

However, passives are best when you want to downplay or even omit the doer of an action. For example:

The money was stolen.
Someone stole the money.

The former can be ideal when we don’t know the doer. Likewise, when we want to downplay the doer:

Professor Tversky is considered a dominant figure in psychology.
People consider Professor Tversky a dominant figure in psychology.

The passive structure is brain-numbing poison in the hands of unskilled writers, but it is a powerful tool for the skilled. Therefore, we should learn to use it only by choice.

Useful style heuristics

To avoid potential confusion, use because whenever we want to use since to imply cause.
To avoid potential confusion, use although whenever we want to use while to imply despite.
When using than, pay attention to the verb we drop after than. “Do you like Coldplay more than Madonna?” usually means “Do you like Coldplay more than you like Madonna?” However, it can also mean “Do you like Coldplay more than Madonna like Coldplay?” for some readers.
A from something to something construction can set up a very long introductory phrase. If your from or your to contains its own from or to, abandon the unwieldy structure and recast it. Also, remember that there’s no comma between the from and the to.
Semicolons often serve no purpose but to show off that the writer knows how to use semicolons. Just don’t use semicolons.
Parentheses usually let writers cram the information they are too lazy to explain clearly to the Reader. Oftentimes, the smaller the parenthetical insertion, the better it works.

Tricky common grammatical mistakes

Relative clauses: restrictive or nonrestrictive?

A relative clause postmodifies a noun. For example, “Any shirt that I wear must be black”. In this sentence, that I wear is a relative clause that comes after the noun shirt and describes it. The tricky part of relative clauses is: A relative clause can be either restrictive or nonrestrictive, but only nonrestrictive ones take commas.

The way to examine whether a relative clause is restrictive or nonrestrictive is to remove it from the sentence. A restrictive clause can’t be removed from a sentence without harming the point of the main clause. Taking out that I wear from “Any shirt that I wear must be black”, we get “Any shirt must be black”. This just ain’t so. Therefore, it does not take a comma.

Restrictive relative clauses do not take commas, but nonrestrictive relative clauses do. Compare these two sentences:

The ceremony will honor the athletes, who won.
The ceremony will honor the athletes who won.

That little comma makes a world of difference. In the first sentence, all the athletes won. In the second sentence, only some athletes won, and they’re the ones who will be honored.

Dangling participle

A participle is a verb form that usually ends in ing, ed, or en. A participial phrase is any participle that serves as a modifier. And it can do so with or without accessories. For example:

Enjoying the ambient weather, Bob got stung by a bee.

The dangling participle is a common mistake where a participle seems to point to the wrong noun. For example:

Walking on the street, Alice’s shoulders got sunburned.

Either Alice’s shoulders can walk by themselves, or we witness the legendary beast known as the dangling participle. Readers usually expect a modifier to refer to the closest noun.

Unclear Antecedents

As Bob and Tom stepped out of the restaurant, the waiter slapped him. He had a panic attack. He cried.

Who had a panic attack? Who cried? This problem is called an unclear antecedent. When we cannot find synonyms or embellishments to point at our antecedent, repetitiveness is better than chaos.

Faulty and Funky Parallels

This car runs fast, well, lasts long, requires little maintenance, and holds its value.

This sentence structure suggests: This car runs fast, runs well, runs lasts long, runs requires little maintenance, and runs holds its value. However, that’s not what we meant whatsoever.

We can fix faulty parallels by adding bits to the parallel items until they’re equal:

This car runs fast, runs well, lasts long, requires little maintenance, and holds its value.

We can also break up the sentence and signals that the list has ended:

This car runs fast, well, and long, and it requires little maintenance and holds its value.

Parallels don’t have to be faulty to be jarring:

She was entertained by the drinks, as well as the comedian.

This is not wrong, but it would be clearer if we repeated the by. She was entertained by the drinks, as well as by the comedian.

That’s my takeaways from the book It Was the Best of Sentences, It Was the Worst of Sentences. Thanks for reading!

Thanks to Angelica Kosasih for reading the draft of this.

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