Tricky punctuation rules that could be killing your credibility

Image licensed via Adobe Stock

Image licensed via Adobe Stock

Are your apostrophes a catastrophe? Are you letting yourself down with suspect punctuation skills? Are you inadvertently putting your reader off your prose?

Punctuation is a time-honoured system to guide your readers’ breathing and speed of thought. Get it wrong, and you’re distracting them from the message content and focusing attention toward the form. That’s terrible news for communication and trust.

To help you combat tricky punctuation rules that could be tripping you up, we’ll now look at some standard stumbling blocks of punctuation: Colons, Apostrophes and Hyphens.

Colon or Semi-Colon?


A colon has three main uses:

1. Where the bit after the colon explains or clarifies the bit before

We had an agreement: first one to win the lottery buys the other a first edition Dickens.

Think of the colon as being a substitute in the spirit of therefore or that is.

2. To introduce a list

The original Wu-Tang line-up was: The Rza, The Gza, The ODB, Inspectah Deck, Master Killa, Raekwon, Ghostface, U God and Method Man.

3. Before a quotation (and in some people's prose style, before direct speech too)

The graffiti on the wall read: “Let there be house. And house music was born.”

When asked if Ringo was the best drummer in the world, John answered quickly: “He isn’t even the best drummer in the Beatles.”


A semi-colon is for splitting up parts of sentences that need something stronger than a comma - but not as concrete as a full stop – to divide clauses.

A clause is a group of words wrapped around a verb that is either part of a sentence or a sentence in itself. The main clause is a clause that would make sense all on its own.

Use a semi-colon when two main clauses exist in balance and are closely linked, e.g. Batman was out fighting crime; Alfred stayed home and tidied the Bat Cave.

You can also use a semi-colon to break up lists (in place of commas, particularly when making a list of points, rather than a list of items).

Apostrophes in action

Correct apostrophe use is a hygiene factor: getting this wrong will irritate readers and erode trust in your prose.

Apostrophes and Ownership

Apostrophes signify ownership. Think of them as a little trademark. If one person or thing owns something, the ’ slides in as part of that word, e.g. F Scott Fitzgerald’s erudite prose.

If more than one person has ownership jointly, the apostrophe goes outside a word, out of respect for the other owners, e.g. Scott and Zelda Fitzgeralds’ apartment off of the Champs Elysees.

Or when the possessor’s name ends in an ‘s’: Charles Dickens’ Pickwick Papers is hilarious.

But it goes back inside the word on plural nouns: Dickens paints vivid pictures of children’s plight in Victorian London.

Apostrophes and contractions

You should’ve also mastered using apostrophes to mash together two words – or cut a chunk out – to present a speedier-to-read, more informal word in its place, for example:

cannot = can’t
should have = should’ve

Use the apostrophe as a signal to show you know what you’re doing when cutting and mashing. Put the apostrophe in the place of whatever you’ve cut, at the cutting point as it reads right to left. For example:

Mick: "I cannot get no satisfaction – that doesn’t bloody scan, Keef."
Keef: "It’s alright bruv, stick in an apostrophe to make it shorter, can’t we?"
Mick: "And besides, it’s a double negative, innit?"
Keef: "We’ll talk about that later…"

Its / It’s

It's a strange one: a well-trodden stumbling block for even highly experienced writers, and the last thing to come out of many a draft. I think this rule will probably evolve out of everyday use over the next 20 years or so, but for now.

An apostrophe-less ‘its’ signifies possession. If you could replace ‘its’ with a noun (and an apostrophe, the little trademark of rightful ownership) use its, every time. For example: Every Bruce Lee film has its charms.

The only time to use an apostrophe with it is if you are shortening from “it is” and “it has". For example: It’s nearly time to end the apostrophe section…

Apostrophes to make plurals – a no-no?

The accepted rule is that you don’t use an apostrophe to make a plural, but there are certain cases where it has become the go-to mark to get you out of a tricky spot, usually with a tiny word ending in a vowel.

Therefore, it is grammatically correct to write ‘do’s’ to make ‘do’ plural, as in ‘do’s and don’ts’ or cross the I’s and dot the t’s.

Use your best judgement here. Remember, communication and pace are more important than rules. Just be consistent with yourself and your team.

Put an end to hyphenation frustration

Using hyphens to best effect will aid reading speed and comprehension, and keep the reader focus locked tight. Getting it wrong, or not doing it at all, can lead to ambiguity and confusion.

Compound words

When a run of words has a combined meaning, like father-in-law, that makes a compound word: these should be hyphenated, to make clear the singular meaning, e.g. ‘sugar-free’ unequivocally means no sugar, while ‘sugar free’ could potentially mean ‘sugar, compliments of the house’.

Commonly, compound words will be compound adjectives. That means, pairing a noun and an adjective (thing and describing word) to describe another word, for example: After selling 370 million records, Agneta became a camera-shy recluse. I.e. camera-shy is a compound to describe the noun, recluse.

But a compound should only be hyphenated if it comes before the noun. If after, don't hyphenate, e.g. A confirmed recluse, Agneta was camera shy.

Hyphenation also applies when adding participles to nouns and verbs

A participle is a verb with an added flavour of time: i.e. a verb with '-ing' (present) or '-ed' (past).

For example: Solving mysteries is Holmes’ favourite pastime by far. Or: When the case was solved, Holmes smoked his pipe and played the violin.

When participles are added to nouns, they should be hyphenated. I.e. Holmes jumped into a horse-drawn hackney and bellowed ‘follow that cab’.

And adjectives…

Quick-thinking and ill-tempered, Professor Moriarty was a dangerous man.

And compound verbs

A compound verb is combining two nouns to make a ‘doing’ word. For example Moriarty well knew how to set a booby trap. In fact, he loved to booby-trap. Booby-trapping was his thing.

Please note, OED defines ‘booby’ as a ‘stupid person’ and a ‘lout, oaf, blockhead’.

But don't hyphenate phrasal verbs, that is, where you’ve combined a verb and adverb or preposition (words to describe the verb). For example: Raffles the Gentleman Thief whipped his jemmy out of his manbag and preceded to break into the flat above the jewellers.

But do hyphenate if you are using said phrasal verb as a noun. I.e. The jeweller was shocked and appalled to discover the break-in.

A word on compound nouns

I’ve deliberately eschewed detailed discussion of compound nouns: according to OED, anything goes when combining two nouns to pinpoint a meaning – e.g. aircrew/air crew / air-crew.

Other language sites would have you believe there is a myriad of arcane, arbitrary rules governing this area. Creative Boom’s best advice is: read aloud, use your best judgement and be consistent. That way, you can play an active part in the evolution of the English language.

Other uses of hyphens

Joining prefixes to other words, such as: Equally worryingly, post-apocalyptic London is crawling with slimy zombies.

Using prefixes such post creates a compound adjective, as we discussed before, but in many instances, the use of hyphens with prefixes is dying out. It’s becoming more fashionable not to use hyphens for common prefixes like 'pre-' or 'cyber-', and meld them into one word, e.g. Notorious B.I.G. was the preeminent rapper of the late '90s. Or: Cybersecurity is one of the key concerns in cyberspace.

The key is consistency. Find how you do it and stick to it.

Word breaks

Another vital role of the hyphen is showing that a word is divided, usually, so you only have to write a shared word once. For example: The Renaissance happened in the fourteenth- fifteenth- sixteenth- and seventeenth centuries.

Punctuation is about more than pedantry

Keeping your reader engaged is a battle you fight every time you put pencil to paper, or keystroke to screen. Following the rules is a proactive way to minimise the barriers to concentration and keep language processing at the fastest possible tempo. Knowing the rules will help you decide how best to apply them, and develop an up-tempo ‘house’ style that keeps the message to the fore.

Thanks to the Oxford English Dictionary, the ‘lex-icon’ that made this article possible, a fount of words so vast that a printed version weights 62.6 kgs or 137 pounds.