My life presents numerous complications making it hard to plan ahead or get ahead. One simple practice I’ve begun is to stop waiting around for last-minute writing inspiration and instead, generate ideas that can be waiting in the wings, for their chance to step onto the screen and become a blog post, podcast, article or even a book project. That way when some time opens up to write, I don’t spend half that time trying to come up with an idea; instead, I choose from my existing list.
Jon Morrow’s Massive Headline Output
Not long ago, I was listening to a Duct Tape Marketing interview with Copyblogger writer Jon Morrow. In it, Jon said he likes to focus on the emotion he wants to bring out in the reader. The interviewer asked him about his practice for finding that target emotion, and Jon explained that Brian Clark, the founder of Copyblogger, gave Jon an assignment early on when they started working together. Brian told John to write 100 headlines a day for different blog posts and get really good at it.
And Jon did. A month later, he went back to Brian with 3,000 headlines. And Brian was astonished! Because even though Brian had told other people to do the same thing, no one had actually followed through. But Jon did.
By taking on that assignment, John noticed certain headlines made him feel something, and those were the ones that grabbed his attention. So his approach is to focus on what he wants the reader to feel, and then choose a topic and dive into the writing.
We’ve got two things going here…one is this philosophy of writing for emotional results—emotional connection. That’s interesting and we could discuss this in more detail in another podcast. But I want us to pause for just a second and let that number sink in: Jon wrote 3,000 headlines in one month.
In fact, Jon continued that practice of writing 100 headlines a day. He says he got so much out of it for 30 days, he continued doing it for two years, seven days a week. He never took a day off. He wrote 36,400 headlines in one year, and at the end of two years, he’d written 72,800 headlines.
With all that practice and repetition, he got better and better. And he had absolutely no lack of ideas when he came time to write an article!
The 50-Headline Challenge
So in honor of this 50th episode of the podcast, I’m issuing a challenge.
You can take Brian Clark’s challenge of 100 headlines a day if you want to, but I’m going to go easy on you.
I challenge you—and I’m challenging myself, too—to write no fewer than 50 headlines for whatever kind of writing you do…in one week.
If you write online content, you might enjoy playing around with some tools like CoSchedule’s Headline Analyzer or a tool called the “Emotional Marketing Value Headline Analyzer.” You can have a little fun with this.
Fifty might feel like a lot if you’ve never done this before, and the first few could feel clunky, but once you get going, I think you’ll start to feel yourself loosen up, and the ideas will flow.
Headlines Provide Writing Inspiration
In episode 46: What’s the Big Idea, I suggested coming up with the big idea of your piece, your controlling idea, your theme statement, your thesis, to guide your writing. Well, each of these headlines can capture a big idea.
And don’t feel like you’re locking yourself into writing all 50 of these ideas. It’s practice for headline writing, and offers you options when it comes time to write.
Let’s take the challenge. Let’s generate headlines, or titles, so we have options and inspiration at our fingertips, because I don’t want to be stuck sitting around waiting for last-minute inspiration. And I don’t want that for you, either.
Are you ready? 50 headlines. Let’s do it.
Click on the podcast player above or use subscription options below to listen to the full episode.
Resources:
- Duct Tape Marketing interview with Jon Morrow
- CoSchedule Headline Analyzer
- Emotional Marketing Value Headline Analyzer
- #46: What’s the Big Idea?
* * *
You can subscribe with iTunes, where I’d love to have you subscribe, rate, and leave a review.
The podcast is also available Stitcher, and you should be able to search for and find “Ann Kroeker, Writing Coach” in any podcast player.
Featured image design by Ann Kroeker (photo via Pixabay, Creative Commons).
_________________________
52 Creative Writing Prompts: A Year of Weekly Prompts and Exercises to Boost Your Creativity

Sure, you can poke around the Internet collecting writing prompts and creative writing exercises.
Or you could buy an ebook that collects them for you in one place.
Convenient.
Inspiring.
Affordable.
I’m in! Thanks for the challenge! Sounds daunting but fun, and definitely useful! 😉
Kate, I hope you find this to be a fruitful challenge, producing lots of new content ideas! Ten a day for five days will get you 50 headlines. We can do it!
I’m going to dive into this one. Yes, ten a day.
Thank you for this new approach.
I’m enjoying the ten-a-day approach and might keep that up to have more and more ideas. I hope this is fruitful for you.
This is one of my weakest areas: headline writing so thank-you for the challenge. I was in the shop waiting for my vehicle to get done so I wrote 50 headlines in an hour. It was hard! But it was good for me. Were the headlines any good? Probably not, but I am going to try it again. This time spread it out over a couple of days in hopes of improving.
Jessica, thanks for sharing your experience of writing 50 in one hour! Wow, way to go!
I’ve been writing some really bad headlines and, I hope, a few good ones. Something about writing many headlines takes away a lot of the pressure and frees me to try anything in hopes of finding some good ones.
Sounds like this has been fruitful for you, and as you heard in the podcast, Jon Morrow said he got so much out of it, he kept it up for two years. I hope you continue. If you think of it, drop in and fill me in one how it goes.
Hi, heard about your challenge from a blogging friend I met at lunch Friday. We talked about blogging and how to write more and she mentioned you; so I tuned in. I also join Kate’ five minute friday regularly. I am trying to start a series too so this is very valuable timing.
Mary, I’m so glad to meet you and hear that this has been useful for you as you prepare for the series. I think this would be a super idea to generate each post in your series. Drop me a line to let me know when your series goes live, would you?
Thank you for this tip. I’m gonna try to do the challenge. I’m not gonna publisch it here, because this challenge is over, but it might do me some good to get started and find my words again. ( writers block 😉 )
Thea, I was hoping people would pick up and try it whenever they stumbled on this podcast! And I really hope this unleashes some hopeful ideas for you, to smash through that writer’s block.
If you see this, would you write me and tell me more about that block? What brought it on (if you know), and what happens when you try to write but feel blocked?
Oooh, I think I’m going to try this challenge for a week. I’ve heard people say they write the headline first before starting a piece, and now when I read your post, I understand why. I usually write headlines about halfway through my writing process, but it’s true it’s so much easier to write when you know where you’re going right off the bat!
Betsy, let me know how it goes! I think people should try this whenever they come across the idea, because it’s such a great thing to practice. If you write the headlines like this, they serve as miniature thesis statements or thought-provoking questions that lead to your thesis.
Late to this party, but so in! 10 for 5 days sounds like a happy change from writing poems.
You’re never too late to get inspired! You may open up a whole new angle to your writing life, dipping into prose. (Of course, your “headlines” could actually be titles to poems…)
I’m so glad you are diving in–and I’m so glad to meet you here and on Twitter!