Years ago, I wrote what I thought was the perfect ad: smart copy, clean design, and a headline I was proud of. When the results came back, though, the numbers told a different story: almost no one read past the headline.

That was the day I learned the hard truth about copywriting: the headline isn’t just the first line. It’s a doorway and if people don’t step through it, nothing else you’ve written matters.

The Reader Always Comes First

The mistake I made back then, and that so many writers make, is starting with the brand instead of the reader. It’s tempting to lead with what you want to say: how innovative the product is, how unique the service is.

But here’s the reality: readers don’t care. They care about themselves: their problems, their needs, etc. A headline that says “Never Lose a File Again” will outpull “Advanced Cloud Storage Technology You Can Trust” every single time, because one is about the reader and the other is about the brand. The moment you start writing from their perspective, the work shifts. Headlines stop sounding like billboards and start sounding like solutions.

Clever Isn’t Enough

I’ll be honest: I love a clever headline. There’s a special satisfaction in landing a perfect pun or a smart twist of words. But clarity beats clever every time. If the audience has to stop and decode what you’re saying, you’ve lost them. Cleverness should be the cherry on top, not the foundation. Think of it this way: clarity gets them in the door, clever makes them smile once they’re inside.

The Weight of Specifics

Another thing I learned over the years: vagueness is the enemy of persuasion. “Save money on prescriptions” feels like a nice thought. But “Cut your prescription costs by 40%” feels real, measurable, and worth clicking on. Details like numbers, timeframes, and tangible benefits transform headlines from fluff into promises. And people respond to promises they can picture.

Brevity Wins (Most of the Time)

The best headlines feel like they can be read in one breath. That’s why short, punchy lines tend to win, especially online. But here’s the nuance: sometimes a longer headline works if it’s irresistible. “How to Stop Wasting Hours on Reports and Get Back 10 Hours of Your Week” isn’t short, but it’s so benefit-driven you’ll keep reading. The rule isn’t “always short.” The rule is “always scannable.”

Let the Audience Decide

Even with all these principles, you’ll still be surprised. Headlines you thought were brilliant might flop. Ones you wrote off as boring might soar. That’s why testing matters. Let the audience cast the final vote. It’s humbling, but it’s also liberating. You don’t have to be right all the time. You just have to be willing to test, learn, and adjust.

Beyond the Formula

You’ll hear a lot about headline formulas: the “how-to,” the list, the question, the promise. They work because they tap into human instincts like curiosity, fear of missing out, and desire for quick wins. But formulas aren’t the goal. Connection is. A headline works not because it follows a structure, but because it speaks to someone directly, at the right moment, with the right words.

The Headline Mindset

Now, whenever I sit down to write, I think back to that first failed ad. I remind myself: the headline is not decoration. It’s the doorway. If I can make the reader curious, if I can make them feel seen, if I can give them a reason to keep going, then the rest of my copy finally has a chance to do its job. And if I can’t? Nothing else matters.

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This is the third post in my “Copywriting 101” series. Next up: The Secret Sauce of Great Copy: Calls to Action That Convert.