Before the Headline

What we lose when we start writing with the ending already in mind.

The subject line stopped me mid-scroll: “Your Inc.com Application.”

I tapped it open between sips of espresso — and there it was: “We’d like to invite you to be an author at Inc.com.”

My heart kicked up a beat. Tomorrow’s client meeting is going to feel good, I thought, already picturing his reaction. What I didn’t realize then was that a few days later, on a call with an Inc. editor, I’d stumble upon what felt like a writer’s secret code.

At the time, I was running this client’s podcast — growing slowly but steadily — when he suggested we apply to a few of the well-known business magazines. “This,” he said, “will give us more authority when inviting bigger names to the show.”

After months of forms and cold emails, we finally got the reply we’d been waiting for: he’d become an author at Inc.com. As his ghostwriter, I was invited to the onboarding call with one of their editors.

During the call, we went through the usual motions — how we’d communicate, how to submit and review drafts, and the obligatory reminder that Inc. isn’t a place to pitch your products but to deliver value to readers. But toward the end, the editor shared something that caught my attention.

We’d been experimenting with different writing approaches,” he said, finally breaking the monotony of the call — “and there’s one thing that’s consistently improved our results.”

“We split the writers into two groups,” he continued. “One wrote the piece first and added the headline later. The other started with the headline — and built the piece from there.”

He paused deliberately, clearly waiting for someone to ask. I took the bait. “So what happened?”

“The headline-first approach won. By miles,” he said, a grin spreading across his face.

He went on to explain why he thought this was the case, but the “why” didn’t really matter. The numbers were there to prove his point.

Over the next few months, I kept getting emails from Inc. featuring the “Top Headlines of the Month,” each one reinforcing the same message: headlines were the key to success.

And I believed it. I wouldn’t write a single word until I had the perfect headline.

I’d obsess over everything — the word count, the balance between clarity and curiosity, how well it matched the magazine’s voice. I’d read it aloud to test its rhythm — did it flow or stumble? A good headline, I’d heard, clicked musically.

Ultimately, some of the pieces drew thousands of views, while others barely made a ripple. The Inc. badge helped us land better guests on the podcast. But looking back, I don’t remember the views or the guests — only the nagging sense that something essential about writing had slipped away.

The Picture on the Box

The idea of headline-first reminds me of a puzzle.

You start with the image on the box — the polished vision of what it’s meant to become — and then spend your time filling in the blanks, fitting each piece into place until it all comes together.

It’s orderly, even satisfying. But it comes at the expense of discovery.

When you start by chasing the perfect headline, you’ve already fixed the image in your mind. Every sentence becomes a piece to confirm that vision instead of uncovering it. You’re no longer exploring an idea; you’re proving a point. The joy of surprise fades — and with it, the chance to find something you never expected to see.

What I eventually realized was that the better I got at the headline-first approach, the less alive the work felt. My writing started to sound condescending — less like a conversation, more like a lecture. Instead of bringing the reader along for the journey, I stood at the finish line, handing out lessons as if I held the key to some hidden kingdom.

Some articles gained traction, but none stirred anything in me — and, I suspect, in the readers. I’d finish a piece and feel a brief pulse of accomplishment, followed by a quiet void, as if I’d assembled something flawless but devoid of spirit.

I began to see how easily a method meant to guide us can end up confining us, and how it can subtly dictate what we’re allowed to create.

In the short term, it might soothe our anxiety. It spares us the practice of enduring uncertainty, relinquishing control, and accepting the creative process as something organic rather than a line of production with a manual attached.

But as with any process that begins with a rigid step shaping everything that follows, you end up offering something polished and familiar instead of risking what is raw and strange. It strips away the mystery that makes writing worth doing — because when the path is already mapped, where’s the thrill?

The First Piece

I understand why some content strategists might think headline-first. Their work depends on attention — on finding a process predictable enough to deliver consistent results. The headline is their compass.

I, on the other hand, try to resist that.

In most of my essays, the headline comes last — a reflection of the essay’s soul, not its plan.

What comes first changes every time, but over time I’ve noticed a pattern — it usually starts in one of four ways.

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Start with a question

Sometimes it’s a question I see another writer wrestling with; other times, it’s one that keeps resurfacing until I can’t ignore it anymore. The best ones don’t have easy answers — they demand to be written through. The essay becomes a way of thinking, not explaining, until the question reveals something about me and the world.

Why Is Writing So Hard? started this way. It pushed me beyond ideas like writer’s block or skill, into the deeper expectations and traps that appear when you try to write something honest.

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Start with a story

Because I’m drawn to stories, this has become one of my favorite ways to begin — even when I have no idea where it will lead. Sometimes I start with something from my own life, like discovering the headline-first method; other times, it’s someone else’s story that captures my attention, like Voltaire’s exile. Either way, the story opens a path I couldn’t have planned.

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Start with a contradiction

Does Self-Help… Help? began with that kind of tension — my attempt to understand why the self-help industry feels both magnetic and unsettling.

Any paradox that makes me feel torn is usually a good starting point.

When I shifted from copywriting — designed to persuade — to more reflective essays, I felt the pull between old habits and new intentions. Working on Writing Without the Need to Convince helped me navigate that shift and name it.

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Start with a thought

Sometimes all I need is a single thought — a seed that grows into 900 or 1,500 words, or more than I expected.

These seeds appear everywhere: while walking, reading, listening to a podcast, or talking to someone. I collect them in a single folder, knowing most will never make it to the page. But the few that do are worth it.

One came from Shane Parrish’s newsletter, where he shared the idea of “small surface area”: “As a rule, the larger your surface area, the more energy you have to expend maintaining it.”

I took that thought and applied it to writing.

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Wherever I begin, I try to avoid picturing the finished puzzle before I start.

I look for a single piece that’s interesting enough to hold my attention, then follow where it leads — through research, reflection, and confusion alike. At times it sharpens what I already sensed; at others, it shows me how little I truly understand.

In hindsight, I see that the lesson from that Inc. experiment wasn’t about headlines at all — it was about control.

Writing for outcomes makes the work cleaner, more efficient, even impressive on the surface. But the real reward of writing for me isn’t control; it’s curiosity — the willingness to stay with what’s uncertain until it reveals its shape. The headline might come later, but by then, the piece has already done what it was meant to do: teach me something I couldn’t have found any other way.

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