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R/GA vs Critical Mass?
Which house are you choosing? 😎

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Write 1000. Then do it again.
Be Tom McElligott.
Yep, 72 is spot on.
But don't worry. The good news is every line you write not only gets you closer to the perfect headline on this project, it also makes you incrementally better to increase your batting average going forward.
My first ad class in college, Stavros Cosmopulous opens a block of Post-Its and says "Take one. Your assignment is Joe's Tattoo Parlor. Fill it."
There are 100 stickies in a pad. That first week, nobody got more than 25, and of course they were all horrible. By the end of a year, we could get 100, with maybe 10% we weren't ashamed of.
After 20 years, and thousands of stickies (now in digital form) for every assignment, I'm up to maybe 25% showable (with exponentially higher standards), and only 4-5 in the realm of "perfect".
Keep it real - like, be honest. Also, the first rule is clarity. It’s easy to get too clever and lose the point of your headline.
Write it straight. Then write it great.
Start saving all of the headline driven ads you find in a folder on your computer. Find the twist or insight that makes them so good. There are some really solid Pinterest boards with collections of headline driven ads. Then write hundreds and hundreds and see what sticks. I love writing scripts, but nailing a perfect headline is the pure,uncut cocaine of copywriting.
72 and sunny is right. Write 1000, then decide they are all shit. Write another 1000.
You must have the right hammer 🔨
Show it to someone.
Watch how they react.
Realize that no one cares and then they all start sounding awesome?
Copy and paste
Wright loads of them. Until you're bored of it.
Then do something completely different and the perfect headline will pop into your head. Usually in the morning when you're in the shower.