being clear vs being clever: how quirky copy can cost you clients

Christine Wilson
Sep 23
3 min read

A while ago, I was on the UP Express, a train in Toronto that takes people from Union Station to Pearson Airport (hence “UP”), when this sign caught my eye:

I know Toronto. I know its train system. Yet, I had to read the thing a few times before I understood what it was saying.

That’s a problem.

The sign is trying to be clever: “Rideshare prices are going UP… take the UP Express instead.” Except there are a few things that make me wave my finger and go ‘tisk tisk’. Here’s what’s wrong:

Although it’s written only once, you have to read the word UP twice for it to make sense. The definition of UP in both of those reads also changes.
It assumes you already know that UP is the name of the train, which is particularly bold for something that will be seen by people from other countries, given it’s going to and from the airport.
And, because we’re in Canada, it mirrors the whole thing in French, so your eyes are bouncing back and forth between two side-by-side messages, whether you want them to or not.

I knew I couldn’t be the only one who resented it, so I took to Reddit, and sure enough, I wasn’t alone. I found a post on r/toronto titled: “Is this sign stupid or am I?”

The split was about 50/50: half confused, half convinced the wordplay was obvious. And hey, maybe this was secretly a genius marketing plan to generate searches and discussion around the UP Express (though, I doubt it).

From my point of view as a copywriter: if even one person stumbles on your message, the copy isn’t working.

That’s the downfall of trying to be clever.

clever vs. clear: why it matters

Clever copy can be fun. Done well, it can feel witty, make someone smile, and be memorable. But cleverness only works if the audience gets it; it relies on shared knowledge, cultural cues, or insider context.

Clear copy, on the other hand, leaves no doubt. Its job is simple: make the message easy to understand and drive action: click, book, buy, sign up. If someone has to stop and decode what you mean, you’ve missed the mark.

The UP ad is a perfect example of sacrificing clarity for cleverness. Instead of simply saying: “Skip the rising rideshare prices. Take the UP Express to YYZ for $12.35.”…it became a puzzle.

Every extra second of confusion is a chance for someone to check out. Most people don’t care enough to reread. They’ll glance, and if they don’t get it, they’ll move on.

If your copy relies on someone already knowing the context (like what “UP” means here), you’ve narrowed your audience down to insiders only. Everyone else? They’re already in the Uber.

here’s what to do instead

make clarity your first priority

Before you think about wordplay or tone, ask: “If someone glances at this for two seconds, will they understand the point?” That’s the true test. Your hero tagline, subject lines, calls to action (CTAs) – they all live or die in that first blink. If the core message isn’t obvious, quirky phrasing doesn’t matter.

test it first

Don’t just run copy by your own team (you’re already too close to it). Share it with people outside the project, such as friends, colleagues, and even someone who doesn’t know your product. If one person is tripped up or needs to reread it, that’s a moment to take a step back and rethink how you phrase it. Because as evidenced by that Reddit post, confusion compounds fast in the wild.

add clever touches only after the message is already clear

Think of cleverness as the garnish, not the main meal. A witty phrase can stick, but it only works once the message itself is solid. If the “joke” or “play on words” is doing the heavy lifting of clarity, it’s in the wrong place.

always assume the reader has zero context

You know your product, your campaign, your brand inside out. Assume no one else does. They’re coming in cold, possibly distracted, and likely multitasking. Write as if this is the first time they’ve ever heard of you. For many, it will be.

a final thought

That UP Express sign is a tiny example of clever copy gone awry, but the lesson is bigger: if someone local who knows the train has to pause and think too hard about it, the copy has failed.

Help your audience think less, and understand more. Clarity is what connects. Clarity is what converts. Cleverness is just decoration.

If you’re not sure your brand’s copy is landing the way it should, that’s where we come in. We help brands cut through the noise and say what they mean: clearly, simply, and in a way that gets people to act.