Cue: instant anxiety attack.

In a Facebook group, I had just announced my experiment for the next 100 days:

Write 100 headlines for 100 companies in 100 days.

To which a certain someone posted this comment:

Joel is a Copyhackers veteran. I have tremendous respect for him.

So I naturally felt nauseous when I read his words of… what’s another word for “dyspepsia”?

His follow-up comment didn’t help:

The room started spinning.

My breath was shallow. My stomach made tiger noises, and I might have peed a little. What the hell had I just committed to?

For some unimaginable reason, I soldiered on, convinced I could prove Mr. Joel Klettke and all the [super-sane] naysayers wrong. So I began….

The terrifying climb to 10,000 headlines:
What I did every day for 100 days (even when it hurt)

Each day, I’d pick a topic to write 100 headlines about.

Oh, that’s another thing: every day, I’d write about a different topic. Because 100 headlines in 100 days wasn’t crazy enough – I needed to add that extra edge of insanity.

So each day I’d dive into a site for The Topic of the Day. Things like:

And I’d see what the players in that world were doing. (For consumer products, I’d check Amazon reviews just like Jo taught me.)

Then I’d write my headlines – more about that very soon – and share them with my growing list of 53 interested-in-watching-me-fall subscribers. My first few posts to those fine folks – which you can check out here – were ROUGH. See, I had no process. I was doing what we all do when we start writing copy but don’t really think about it as more than words on a page. My hacked process went like so:

  1. I’d write as many headlines as I could (without a template or starting point),
  2. Identify themes in those headlines,
  3. Highlight a few words,
  4. Hit a wall and
  5. Glance at my list of ~400 headline formulas.

Each time I glanced at those formulas, I generated anywhere from 3 to 8 new headlines. Some stuck too close to the template. Some were the product of what was clearly the wrong mindset. Some went off the rails entirely. If you want to see how disparate a group of headlines written fast can be, check out my Tutorial Tuesday replay here, where I live-write a bunch of headlines in this reusable Airstory headlines template:

Sometimes I’d catch a hot streak and 100 headlines seemed to write themselves. Those days were magic.

It won’t surprise you to find that, as the days wore on and as 100 headlines turned into 2500 headlines, I learned a bunch of stuff. Like, I learned I’d need to adjust my voice rather than fit each topic into my voice – something I had completely overlooked during concept and something that was, alone, worth learning over the 100-day experiment.

That was a small lesson.

Five much larger lessons cropped up, which I’d love to share with you now (before we get into the pain of 10,211 headlines)…

[Tweet “The 5 big content lessons @prettyflycopy learned during his “100 headlines a day” experiment, on @copyhackers”]

Lesson 1: What headlines actually are.

Turns out each day was not an exercise in finding “100 ways for Justin to phrase things.”

It was an exercise in finding “100 value propositions for the company.”

Headlines are – very often – variations on a value proposition.

When I realized that, I found myself in a tricky spot. This was no longer a side experiment. This was a job. I was doing the work of copywriting. I instantly knew what Joel had hinted at:

The project might not be so fun.

BTW, I should mention I’m an in-house writer with a day job. So these posts were in addition to my full-time gig. And client work. And family time.

Lord help me if I had a lunch meeting – I had to tack on extra time in the evening. On weekends, replace “work” with “client work.” …Have I mentioned my wife is a saint?

Within 10 days, I could whip up 25 headlines in minutes – no template needed. Common formulas ingrained themselves in my brain and I started each day with lines like:

  • For ___ who want to ___
  • Get ___ without the ___
  • Helping ____ do ____
  • The only ____ that doesn’t ____
  • The (good news) inside (bad news)

These first headlines would never be the best of the bunch, but they eased me into the post. Writing them gave me a rhythm. I’d often find the germ of a better headline in the first attempts. It was the crappy first draft every copywriter needs.

As I mentioned, I started with about 400 headline formulas. As the first 10 days went by, I eliminated 110 formulas from my template. Some were duplicates, some were lazy… and others felt manipulative (more on that later). But a handful rose to the top.

By Day 20, I was rolling. I adapted recurring themes, discovered how to really empathize with the customer and found myself digging deeper. I even used a few lines in my client work and day job. And when I missed a single day? I felt so bad that, the following afternoon, I wrote 200 lines.

By now I was writing headlines like:

Headlines in the early days

On Day 30, I felt like a whiz. Whipping 50-60 lines off the top of my head, no problemo. My subscriber list was growing. I started tinkering with themes from the 7 deadly sins, and I was sailing smooth. Sometimes a bad list of headlines cropped up, but no worries. I felt good. I felt alive.

I felt smart.

I should have expected what followed…

Day 40 brought complete and total burnout.

I was tired. I wasn’t sleeping. And my brain was drained.

Actual video of me at work

Also, my wife was over it. My kids had stopped asking me to play with them because they knew I’d say no. It was a dark time for the rebellion. If it weren’t for Joel’s quote on my screen – yes, I made it my screensaver – I might have given up.

On Day 50, I gave myself a day off. I still posted for my readers, but I didn’t write my 100 headlines. I broke the streak.

It felt GREAT, to be honest.

One day off wasn’t enough to make me a good family man again, but, hey, it was a start. Which brings me to…

Lesson 2: Take breaks.

Recharge your soul. Your sanity (and your family) will appreciate it.

By Day 50, I also changed the way I approached topics. I picked fun brands. There were a lot of Shark Tank products, weird Kickstarter campaigns and ridiculous items like mailable potatoes, light-up toilets, and wine for cats. Strange as it was, I loved these. I wrote headlines like:

Potato parcel headlines

Maybe this was my niche??

Just like that, two more big lessons smacked me in the brain…

Lesson 3: If you’re not enjoying the process, change the process.

This feeling might mean that you’re doing it wrong.

Keep tweaking until you find your fit.


Lesson 4: The way you’re thinking about a “niche” may be entirely wrong.

I was looking for a category when I should have been looking for a voice.

The WHO mattered more than the WHAT.

Days 50-70 were light. I collaborated with other writers, like Lianna Patch, Alaura Weaver and Hillary Weiss, who let me write headlines for their existing content. Working with them made me step up my game. Because not only would I have to emulate their voice, but I’d also have their feedback. They’d be the judge of the lines.

Those posts made me feel so much less alone.

And I gained some street cred. People were reaching out to me, and I landed 3 podcast interviews. Recognizable names – like Joanna Wiebe! – subscribed to my recap or followed me on social.

I had become “The Headline Guy.”

I was getting faster, too. I could hit 80+ lines without referring to the list of formulas and often knocked out full lists of 100 headlines during lunch. This meant more free time at home with my family—something I did not take for granted.

[Tweet “By the time @prettyflycopy had written 7000 headlines, he started to get, well, kinda good at it”]

On Day 71, I went full masochist.

I threw out the list of formulas.

I took 37 classic direct response headlines, printed them out… and that’s all I used for the last 29 posts. From that point forward, it was Eugene Schwartz, John Caples, Jay Abraham… and me.

Things got veeeery interesting.

I revisited previous topics, chose a few I was afraid to tackle earlier, and homed in on brands I thought would be fun. By focusing on the direct response examples, the lists became more emotional. I was hitting on fears and wishes. The lines had more story. More empathy.

But there was a dark side.

I teetered on clickbait. (BTW, I *hate* clickbait. In fact, an underlying theme of this project was to prove clickbait shouldn’t exist. I was tired of clicking ads that used the work of copywriting geniuses only to be taken to disappointing articles. Eyes on you, BuzzFeed-style-headlines.)

I wanted only to use the power of these direct response classics for good. Because I knew, with a little extra effort, writers could properly manage expectations. So I dove into the curiosity behind the lines and phrased them to be more positive.

The new style took longer to write – some posts clocked in at 2 hours – but that was OK. It meant I wasn’t coasting. I was challenging myself.

I also cashed in a few mental health days. I still posted but didn’t write a list of headlines. This helped me regulate my sanity, remember my kids and spend time with my wife. Plus, it eliminated the soul-crushing anxiety that paralyzed my brain when I blanked on ideas for topics. I needed those small breaks.

By this point, I was getting fast, I was getting good and I was finding my groove not with 100s of headline formulas but with a small list of awesome ones. Next up, I found myself diving deeper into emotions I hadn’t really explored in my copywriting before – emotions like:

  • Fear
  • Frustration
  • Powerlessness
  • Anger
  • Betrayal
  • Revenge

The lines were good.

Probably some of the strongest I’d written.

But I didn’t like going to The Dark Side.

It felt manipulative. I realized that writing aggressive-style copy just isn’t me. More validation that – to me – voice is more important than topic.

On Day 90, I struck a balance between bolder emotions and the formulas I had memorized. I went back to The Light Side. Security, happiness, relaxation, hope. Ah, now this was me. And my headlines were – objectively – far better than where they’d been back at Day 20 or when I went to the Dark Side. Here’s a snapshot of Day 95:

When writing headlines gets better

At Day 100, I was ecstatic. I had written 10,211 lines. 100 days of posting. 106 days of writing headlines. Yes, it took a few extra days, but nobody seemed to care.

Lesson 5: Family first. Always.

I had learned a ton.

Mostly, that The Headline Project wasn’t fair to my family. I was a shitty husband and father for 3 months. I know that’s not the lesson you want to read, but I cannot overstate the importance of family first. I’m lucky the damage I caused was only temporary. Now my wife smiles and my kids rush me for hugs again when I come home. Because it’s playtime.

As for what I learned during the whole process, well, that’s the whole reason you’re reading this, isn’t it?

So, here we go…

16 hard-earned headline takeaways

1. There are no shortcuts.

Do the work.

No hacks, article, or template can match putting on the gloves and getting dirty. There comes a time to stop reading and start doing. Practice makes permanent. It’s the only way to make things stick.

2. Clear beats clever. But sometimes you can do both.

Some of my favorite lines were direct and infused with personality.

Like these ones:

  • Once you learn to think on your feet, it doesn’t matter where you’re standing (Dumore Improv)
  • Sorry. We don’t believe in wedgies (Pair of Thieves Underwear)
  • Send a potato. It’ll still be funny when you’re sober (Potato Parcel)
  • Just because dating can be awkward doesn’t mean you need to be (Nuphero Pheromone Spray)
  • Where we write like Ogilvy & drink like Hemingway (The Copywriter Club)

They’re fun, but and they make sense. Those headlines all came late in the day’s post – often in the last half – so you need to dig.

[Tweet “Dig to find the best copy, via @copyhackers @prettyflycopy”]

3. Don’t force your personality.

Sometimes I made light of sensitive topics. The biohazard cleaning post comes to mind.

But if you need these guys, it’s not a time to joke. Don’t put funny where funny doesn’t belong.

(Yes, this may sound contradictory to the whole voicey-nichey thing, but it’s not. This is something that wouldn’t be in my niche. See, I struggle to keep myself out of my writing. I need to find brands where that’s a fit.)

4. Boring topics don’t need to be boring.

Some of the tech sites were super nerdy. Bland copy for good software. And it’s a shame because they’re products that everyone can use.

However, the average consumer couldn’t understand what they do.

Surprisingly, these posts were fun to write once I swapped features for benefits:

  • Make your data sexy (Plotly graphing software)
  • Helping families make it through long weekends without WiFi (Duracell batteries)
  • Park your domains in a friendly lot (Domahub)
  • Speed reading isn’t a skill. It’s a Chrome extension (Spritz speed reading app)
  • How to animate your presentations like Pixar (Whiteboard animation agency)

I mean, I’m still not the guy to pitch a tech company. But if they asked me to explore the mainstream, I could give it a go.

5. Learn what you suck at.

Brands targeting women ain’t my thang. And that’s OK. Knowing this helped me turn down a project I now know I never could’ve done right.

6. Great things happen when you become your audience.

Remember Freaky Friday, The Change-Up or The Hot Chick? Or any of the other bazillion movies where characters change bodies?

After the initial flow of lines ended, I’d close my eyes and imagine myself as the consumer.

I’d mentally put myself in their body and ask myself:

  • Who would I be?
  • What would I want?
  • How would I feel?
  • Which pains hurt most?
  • What’s missing in my life?

Suddenly, the headlines were easier to write.

7. Writing headlines for a company you *think* you want to work with may result in a very different outcome.

I wrote 100 lines for a brand I had unsuccessfully cold-pitched.

Turns out, I struggled to find their voice.

I’m glad they didn’t get back to me. I wouldn’t have been a good fit. Now, before I reach out to a company, I practice.

Y’know, just in case they say yes.

8. Consumer products can be surprisingly fun to write about *if* they provide real value.

I never wrote much about physical goods before this.

But 7 of my top 11 posts were for products. And they were fun! I didn’t love writing about things you buy just to have (e.g., shirts, toys, grilling accessories), but if it adds value to your life – even if just a laugh – I’m all about it.

9. Google Images is a gold mine.

The day I accidentally clicked “image results” was a game changer.

I was writing about owl rescue, and I was stumped. When I saw the pictures, memes, movie stills and gifs, it was an awakening. The Harry Potter theme alone provided enough inspiration to finish the post. I never would’ve made that connection.

Now, whenever I get stuck, I go straight to images.

10. Write like Dr. Seuss.

Let your mind get silly. Funny rhymes, alliteration and a little wackiness are great for getting into a flow.

No, you’re not going to use them on your final product. But the path they lead you down might take you to your goal.

Here’s what I mean:

  • Rain, rain, go away. I’ll stay dry & watch them play (Under The Weather Sports Pods)
  • Would you, could you, on a boat? (Florida Sailing Club)
  • Sticks and stones may break your bones, but my words will make you money (Pretty Fly Copy)  (ß actually, I did use this one on my final product)

11. Bold the important words.

Identify the keywords in your sentence.

Delete the rest.

Now go make new sentences with what remains. Tinker enough and you’ll find your line.

12. Templates have a place in this world.

I’ve never been one to rely on templates. It always felt like color-by-numbers. But now I see, when you add your own spin, they have tremendous value.

That being said, here’s an Airstory template with the headline formulas I used during my 100 days. To help you kick-start your own headline writing.

Use the formulas in Airstory

13. Clickbait is never OK and I will punch you in the face if you say different.

Because it’s lazy. In one post, I intentionally wrote in BuzzFeed’s style and it took zero skill. No effort, no challenge and no concentration. I could’ve written it while riding bareback on a zebra and cooking soup.

Stop wasting curiosity headlines on disappointing articles. It makes people hate you.

Instead, focus. If you’ve got a great headline on a shitty article, rewrite the article. You’re better than that.

14. “Copywriters aren’t born. They practice.”

I don’t know who to attribute this quote to, but they’re right.

Writing 10,000 headlines helped me nail messaging more than reading any article ever could.

Now instead of sifting through 41 million search results, I’m writing better.

15. Hard work never gets easier.

This project was like shooting myself with a gun each day to build a tolerance to bullets. It never didn’t hurt. But I learned I can take the pain.

16. Everything I learned about how to find my niche was wrong.

Wrong for me, I mean.

I was all over the map for 3 months. Sporting goods, bottomless muffins, poop-scented candles… You name it, I wrote about it.

And here’s what I found: the voice of the brand matters just as much as what they sell.

I want to work with fun, casual brands. Because that’s who I am.

[Tweet “The voice of the brand matters just as much as what they sell via @copyhackers @prettyflycopy”]

So, I’m helping web-based services with taglines and easy-to-read copy. Simple messages for complicated businesses. It’s not something I ever would’ve focused on before, but it turns out, I’m pretty darn good at it.

TBH, between you and me, I’m still trying to figure it out…

Day 100: So, can I take on Caples, Schwartz and Ogilvy now?

Writing 100 headlines a day doesn’t mean I can beat a control.

  • It means I can think quicker and faster.
  • It means the common formulas are familiar and I have a mental database to pull from.
  • It means I can dig deeper than most people. I won’t stop until I strike gold. Oh, and I can probably find said gold in less time.

But am I better than YOUR best line? Well, that depends on you.

To win you need to test. You need to study your audience and feel their pain. And you need to be able to solve it. I explored ways to help people, but I never actually did it. I did write some great headlines though…

Should you do an experiment like The Headline Project?

A lot of people reached out to me when I finished. People wanted to work with me. People wrote to me the same way I write to those I admire.

Even Joel Klettke gave me a virtual pat on the back.

Best part was: it felt earned. I didn’t feel like an imposter.

The Headline Project gave me a seat at the big kid’s table. It crushed me at times, but it built me back up. It allowed me to re-prioritize my family into first position, and it gave me a path. More importantly, it grew the quality of my network. Admirable writers are now acquaintances. I’ve spoken at a summit. I’ve been recognized at events. And people email me for advice.

Would I recommend you do it? Maybe.

Anyone CAN do it. There’s nothing special about me. This wasn’t any easier for me than it would be for you. The only difference is that I did it.

And I’m glad I did…

…But I’m happy it’s over.

Stop waiting for permission.

There comes a point when you need to walk away from more lessons, more training, more videos – and get to work.

I didn’t get paid for The Headline Project. Nobody told me to write. I just did it.

So whatever your big idea is – a blog challenge, growing your list, finding your voice – whatever thing you’ve been reading about for months, you don’t need approval to begin.

And if permission is the thing you’ve been waiting for, here it is. I give you permission to start.

Go do something cool.


Photo by Nathan Dumlao on Unsplash