The Curse of the Clever Sentence

There’s a kind of sentence that writers love and readers pay for. It’s the clever one: the pun in the headline, the twist on a familiar phrase, the line constructed to be admired. Writers produce these in their best moments, when the caffeine and the deadline align, and they can feel the sentence click into place like a well-made joint. The trouble is that the click the writer feels and the experience the reader has are two different events, and on a website they’re usually opposed.

Consider what a clever sentence actually asks of its reader. Wordplay works by meaning two things at once, which means the reader must compute both meanings and then notice the relationship between them. An allusion works by pointing at something outside the text, which means the reader must have the reference and retrieve it. Irony works by saying the opposite of what’s meant, which means the reader must detect the inversion. Every one of these devices is a small puzzle, and puzzles take attention. In an essay read for pleasure, that attention is the point; the puzzle is the entertainment. On a website, the reader’s attention is already spoken for. They’re trying to figure out what you sell, whether it fits their problem, and what it costs, on a phone, in the time it takes an elevator to arrive. A puzzle inserted into that task isn’t a delight. It’s an obstacle wearing a bow tie.

The headline is where the curse strikes hardest, because the headline is where writers try hardest. A headline reaches more readers than any other sentence on the page, so it attracts the most craft, and craft, unsupervised, drifts toward cleverness. The result is the homepage that greets you with something like “Beyond the horizon of ordinary” and no clue what the company does. The literal reader, and every skimming reader is a literal reader, extracts nothing. Meanwhile the plain alternative, “Accounting software for restaurants,” would have done its whole job in half a second. The clever headline optimizes for the reader who will dwell on it; the web supplies almost no such readers. It’s a joke told to an empty room, at the cost of the introduction that the full room actually needed.

I think the root of the curse is that clever sentences are written for the wrong audience. The true audience of a clever sentence is other writers, or the writer’s colleagues, or the writer themselves rereading it with satisfaction. Cleverness is a bid for admiration, and admiration comes from people who can see the difficulty of the trick. Customers can’t and don’t care. They aren’t grading your prose. They’re using it, the way they use a door handle, and the highest compliment a door handle gets is not being noticed. When a reader stops to admire your sentence, they have stopped, and stopping is exactly what a website’s prose exists to prevent.

There’s also a trust cost that shows up before any parsing happens. Readers have been marketed at their whole lives, and they’ve learned that verbal flash correlates with weak goods. The plainly stated offer, “we do X, it costs Y,” signals that the seller expects the facts to be persuasive on their own. The lacquered phrase signals the opposite: that somewhere under the wordplay is a fact that couldn’t survive being stated. This inference isn’t always fair, but it’s fast and it runs automatically. Cleverness on a commercial page doesn’t only tax comprehension. It arouses suspicion, which is worse.

None of this is an argument against wit as such. It’s an argument about placement. Wit is expensive, so it belongs where the reader has attention to spend, and never in the load-bearing positions. The headline, the navigation labels, the button text, the pricing rows, the error messages: these are structural members, and structural members should be boring in the way steel is boring. A button that says “Start free scan” outperforms one that says something adorable, because a button’s job is to be predicted, not enjoyed. If you must be charming, be charming in the corners, in a footnote, a confirmation message, a 404 page, where a reader who gets the joke gains a moment of delight and a reader who doesn’t loses nothing they needed.

The awkward truth is that plain sentences are harder to write than clever ones. Cleverness gives you somewhere to hide; if the substance is thin, the shine distracts from it, which is exactly why thin substance attracts shine. A plain sentence has no such cover. “Accounting software for restaurants” only works if that’s genuinely what you are and it’s genuinely worth wanting. Writing plainly forces you to have something to say, and I suspect this, not laziness, is why so many pages stay clever. The pun was easier than the clarity.

Building GazeSite has given me a strange reading habit: I now see websites the way an audit sees them, and the readability findings that stick with me are rarely about typos or grammar. They’re about pages whose most prominent sentences communicate the least, headlines with the informational content of a fortune cookie occupying the most valuable pixels the company owns. The remedy is almost embarrassingly simple. Say what it is. Say who it’s for. Say what it costs. Save the wit for later, if at all. The sentence nobody notices is the one that worked, and the writer’s ego is the only casualty. That’s a good trade. On the web, it may be the only good trade there is.