How to write better headlines by generating at least 50 options

Executive overview

Most copywriters write one headline and move on. That single headline is rarely the best one — it's just the first one. The fix is quantity: write at least 50 headlines every time, using structured techniques to break out of repetitive thinking.

Five techniques force new ideas: add time limits, ask curiosity-opening questions, swap lifeless words for surprising ones, replace abstract phrases with visual word pictures, and borrow from proven copywriting formulas.

The only way to find a great headline is to generate far more headlines than feel necessary.

Why 50 headlines (minimum)

• Writing one headline and committing to it leaves better options undiscovered.
• 50 is the floor, not the ceiling — small word-swap variations don't count.
• Brainstorming mode means no editing, no self-censorship; bad ideas belong on the page.
• Volume builds skill: the more you write, the better your instincts become.

Five techniques to generate new headline ideas

1. Add a time limit — "Bring your financials into focus" becomes "Bring your financials into focus by this time next week."
2. Ask a curiosity-opening question — Avoid closed yes/no questions. Prefer gaps that make readers think: "What if you could bring your financials into focus by this time next week?"
3. Replace lifeless words with surprising ones — Words like fuzzy, atomic, verboten, zeitgeist, wunderkind stop a reader's eye. Most marketing copy slides past readers without friction; one unexpected word creates it.
4. Use word pictures instead of abstract nouns — "A magnifying glass for your business financials" or "a heart rate monitor for your finances" is concrete where "focus" is not.
5. Steal from copywriting formulas — Keep a swipe file. Search Google Images for Eugene Schwartz, John Caples, David Ogilvy. A formula like "food is your best medicine" can be transposed: "financial clarity is your best growth engine."

When to throw it all out

• Over-worked headline ideas harden like over-kneaded dough — nothing useful comes from continuing.
• Delete the batch. Start from scratch. Take a break, then start again.
• If the idea was strong, it will return. Courage to delete is a real copywriting skill.

The three-person test

• Imagine three bored people in a parking lot or at a desk.
• Does your headline actually capture their attention?
• If most of your headlines fail this test, write 100 instead of 50.
• The reaction you want — laughter, curiosity, recognition — should be visible. If it isn't, keep writing.