What Old-School Copywriters Know That Content Marketers Forgot
A few weeks ago, I fell down a rabbit hole. It started the way these things usually do — I was procrastinating on a deadline, clicking through links at midnight, and I landed on an essay by Dario Fontana, a retired advertising creative director in London who writes beautifully about the craft of copywriting. His piece on headlines stopped me cold.
Fontana writes that he typically produces between forty and sixty headline variations for a single advertisement before arriving at one that satisfies him. Forty to sixty. I thought about the last blog post I published. I spent maybe three minutes on the headline. I wrote two options, picked the one that "felt right," and moved on to worrying about the meta description.
This is what we've lost.
The craft gap
Content marketing has a craft problem, and it's not the one you think. The problem isn't that we can't write. Most content marketers write perfectly fine sentences. The problem is that we've forgotten what the old-school copywriters knew instinctively: every single word is a decision, and decisions have consequences.
Fontana describes three tests he applies to every headline: the stranger test (would someone with no interest in your product stop for this?), the promise test (does this headline make a promise the reader wants kept?), and the specificity test (does this contain actual information, or is it a placeholder?). I read those three tests and immediately thought of every blog post I've seen that opens with "In today's fast-paced business environment." That sentence fails all three tests simultaneously. It's an achievement, in a way.
The old copywriters — the Ogilvy and Bernbach generation that Fontana writes about — understood something we've systematically unlearned: the reader owes you nothing. Not a click, not a scroll, not a second of attention. Every word has to earn the next word. This isn't just true for advertisements. It's true for blog posts, newsletters, landing pages, and LinkedIn posts. It's true for everything.
What I'm stealing (respectfully)
After reading through Fontana's essays — and I read all of them, at midnight, in my pajamas, with a cold cup of tea — I made a list of things I'm bringing back into my own content practice. Here's what I'm stealing:
1. Write more headlines than you think you need. I'm not going to write sixty. I'm not Dario Fontana, and I have a content calendar that would make him weep. But I'm going to write at least ten headline options for every piece, and I'm going to apply his three tests to each one. My old habit of writing two and picking the "better" one was not a process. It was a coin flip.
2. Specificity over cleverness. Fontana tells a story about writing headlines for a financial services firm. The previous agency had used headlines like "Investing in Your Future" and "Building Wealth Together." He calls these "not headlines" but "placeholders." When they replaced them with specific claims and numbers, response rates quadrupled. I've been guilty of the placeholder headline. "Why Content Strategy Matters." That's not a headline. That's a surrender.
3. Directness is a skill, not a shortcut. This one hit me hardest. Fontana writes that young copywriters are afraid of being direct because directness feels crude. So they hide behind cleverness. But directness plus surprise — "At 60 miles an hour the loudest noise in this new Rolls-Royce comes from the electric clock" — that's the real craft. It's saying exactly what you mean in a way that makes someone stop.
4. Rewriting is where the work happens. In content marketing, we have a publish-and-move-on culture. Write the draft, do a light edit, schedule it, move to the next piece. The old copywriters rewrote obsessively. Fontana describes finding the right headline on attempt forty-three, from a conversation he overheard in a hotel lobby. That only happens if you keep going past the obvious ideas.
Where I disagree
Now, I'm not saying we should all become 1960s ad men. (For one thing, Fontana writes about restraint with a level of elegance I can only aspire to, and my natural mode is more "enthusiastic dog at a party.")
The old copywriters were writing for a different context. They had one shot — a single print ad, a single headline, a single reader flipping past. We have the luxury of relationship. Our readers come back. They subscribe. They follow. We can build trust over time in a way that a single print ad never could.
And honestly, some of the old-school formality feels exclusionary. Fontana's writing is gorgeous, but it's written from the perspective of someone who's had thirty years to master the craft. Most of us don't have that luxury. We're writing three blog posts a week while also managing a team and attending meetings about meetings. The perfection standard is inspiring but not always practical.
What IS practical is the mindset. The conviction that words matter. That the headline matters. That the first sentence matters. That every piece of writing, even a Tuesday blog post that will be read by four hundred people, deserves genuine craft.
The real lesson
The biggest thing I took from Fontana's essays wasn't a technique. It was a posture. He treats copywriting as a serious discipline — not a service function, not a content widget, not a "deliverable." He treats it the way a carpenter treats wood: with respect for the material and patience with the process.
We content marketers could use more of that. Not the formality. Not the thirty-year apprenticeship. But the respect. The belief that what we write matters enough to be rewritten. The willingness to throw away the first ten ideas because the eleventh might actually be good. Editing is the most underrated marketing skill, and this is exactly why.
I'm going to keep reading Fontana's essays. And I'm going to start writing at least ten headlines before I pick one.
Diane — my old terrifying editor — would approve. Probably. (She also taught me that the first sentence is a promise. I still hear her voice every time I write one.)