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In just 15 minutes a day, learn how you can write better headlines

I’ve been reading a lot about how to write better titles for my posts.

You might have seen me play around with such titles as “Obey This One Weird Rule to Lower Bounce Rates” and “Please Don’t Make These Critical Commenting Mistakes!

The first title was actually a play on those “obey this one weird trick” ads (not a test on my part) you see everywhere and the second one was a riff on the classic “Do you make these X mistakes” copywriting title by Max Sackheim, I would use the classic on social media when I shared it. The title of this post is actually another play on a classic copywriting line by Sackheim.

With the days of easy long tail search dominance behind us, titles now serve a different purpose – they need to draw people into the post.

I’ll show you how with just 15 minutes a day will improve your headline writing skills.

Write 25 Headlines Per Post

That’s it. Just write 25 headlines. How did I arrive at 25? I learned from the pros.

I was talking to James Clear and he sent along this slideshow on how Upworthy gets their posts to go viral. Upworthy doesn’t create it’s own content (they create nothing), they just find great content, give it some sex appeal (mostly, a title), and then helps it spread like wildfire. They’re really good at it.

How To Make That One Thing Go Viral from Upworthy

There is a lot of good information in that slideshow (including what makes great content people will share) but the part that resonated with me, which James brought up in our chat, was how each editor has to write twenty-five titles (slide #23, “you HAVE to crap out 25 headlines for every piece of content.”.

25 titles is a lot of titles. But it gets you to the best title. (Adam Mordecai, Upworthy’s Editor at Large, explains the logic behind the 25 headlines rule)

But that’s how I settled on the title for last week’s post where 87 bloggers shared what they’d tell themselves on day one. You’re basically brainstorming titles. Twenty five titles is enough for themes to emerge, for ideas to battle it out and for the best one to emerge. You end up picking the best pieces of the bunch to integrate into something greater than what you started. It’s essentially “title evolution,” on the best survives.

Curious what that title started as?

The 25 Titles for Day One Advice

Here are all 25, in order (some of them I’m kind of embarrassed about!):

  1. XX Bloggers Share What They’d Tell Themselves Before They Started
  2. XX Successful Bloggers Reveal: “What I’d Tell Myself Before I Started”
  3. JD Roth, Pat Flynn, and XX Probloggers Share Their Advice for Newbie Bloggers
  4. XX Bloggers Worth $30+ Million Share Their Beginner Blogging Secrets
  5. Just starting a blog? Learn these tips from blogging masters.
  6. Woulda Coulda Shoulda: XX Bloggers Talk About Their Beginner Mistakes
  7. What If? XX Bloggers Share What They Would Do Differently
  8. Blogger Time Machine: What XX Bloggers Would Tell Their Day One Selves
  9. What I’d Tell Myself On Day 1: XX Bloggers Reveal
  10. XX Blog Heroes Reveal What They Wish They Knew
  11. Surprising Lessons Learned from XX Successful Bloggers
  12. What I Wish I Knew: XX Bloggers Reveal Their Lessons Learned
  13. Are You Making This Rookie Mistake? XX Successful Bloggers Reveal Their Biggest: “What I’d Tell Myself Before I Started”
  14. XX Bloggers Share The Best Blogging Decision They Ever Made
  15. Bloggers Share Their Mistakes So You Don’t Have To Make Them
  16. Go Back In Time: XX Successful Bloggers Reveal: “What I’d Tell Myself Before I Started”
  17. Don’t Make These Beginner Blogging Mistakes: XX Blog Heroes Reveal Theirs
  18. Advice Worth Paying For: XX Bloggers Share Their Lessons Learned
  19. XX Bloggers, 6500 Words: Successful Bloggers Reveal Their Secrets
  20. XX Successful Bloggers Reveal What They’d Tell Themselves on Day One
  21. Learn from these XX bloggers: what should you do first?
  22. From Day One: XX Successful Bloggers Reveal What Advice They’d Give Themselves, You Will Not Believe Their Answers
  23. XX Probloggers reveal their day one mistakes, are you making any of these?
  24. Day One Advice: XX successful bloggers reveal what advice they wish they knew

You can almost see the title shaping itself over the course of 25 iterations. The good stuff lives, the bad stuff dies. #3 – highlighting a couple bloggers but not others creates tiers… which I didn’t like, that was out. The idea of “mistakes” lives for a few titles but eventually loses out to “lessons learned.” I start to toy with the Upworthy-like technique of “something crazy happens, and you won’t believe the response” but it didn’t feel right.

I struggled with how to capture the essence of the post – I wanted to explain that I was able to get 87 bloggers to share one piece of advice they would tell themselves on day one. I would eventually settle on “Day One Advice” to make it clear this is advice for the first day.

I felt the need to always put that 78 successful bloggers participated, thus giving it some punch.

My next realization was that I preferred the word “reveal” over the word “share.” Reveal makes it seem like we’re sharing a secret, rather than people just talking. It also matches with the content, we are revealing something personal… a lot of bloggers shared a mistake they made and what they’d do differently.

Finally, I made the title more of a sentence rather than a book title (or subtitle).

Is the title perfect? I don’t know but I think it’s much much better after 25 practice tries!

This is a big change from how I would write titles on Bargaineering. Back in the days of search dominated blogging, your title was a keyword-heavy description. A lot of “how to,” “best [whatever],” and “[product/service] review.” The title was wrapped in an H1 tag, it was in the meta, and it became easy to link to the post with nice keywords if they’re in the title.

I think titles serve a different purpose today and if you want to get better at it, you need to practice. And then practice some more. 🙂

How do you work on writing better titles?

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In 2005, I founded a personal finance blog ( that became successful enough that I quit my career as a software developer in the defense industry. It is my goal to share everything I learned so that you can do the same - build an online business that let's you pursue your passion.

12 responses to “In just 15 minutes a day, learn how you can write better headlines”

  1. Glen Craig says:

    Taking some time between writing an article and publishing helps a lot with titles (and the whole article too!). Sometimes you need to look at it with fresh eyes to realize you could do better.

    Lately I’ve been creating pics with text to go along with my articles. The constraint of fitting the text on the pic has helped me to see what words are essential in getting the most punch across in my title.

    • Jim says:

      Sometimes I go back and wonder what the heck was I trying to say? 🙂

      Yeah, I’ve been playing around with that too because of Pinterest. Having a good image goes a long way in getting something pinned and popular.

  2. Michael says:

    Wow. Just spent the time going through that slideshow. It was well worth it as there’s some gold buried in there. It was also instructive to see how your list of 25 headlines morphed as you wrote them. I’d be curious to know which slot (on average) is the best. At some point you’re stretching and will probably wind up stretching too far.

    • Jim says:

      My Facebook feed has been filled with “viral” stuff on other sites that have followed this slideshow to the letter. What we’re seeing is the next iteration of image/text virality, I’d say the next epoch after the ICanHazCheezeburger-style era.

  3. This is great advice! Thank you! I typically write several, but nowhere near 25. I’m wondering if you typically write your headlines before or after you write your post. I had always written them after but then sometimes I’d have to change my post to match the headline I ended up liking.

    I recently read that you should write headlines first because the headline is like the promise and the post is you delivering on your promise. The author argued that it’s hard to deliver on a promise you haven’t made (if you haven’t written the headline yet). Therefore, you should always write your headline first and then it should be easier to write the right post.

    • Jim says:

      I write it after, I have a working title and then I go back and grind out 25 titles. I don’t do it for every post, just the “big” ones that I think offer a lot of good & broad information and have staying power.

      If I do make a promise or an an angle that wasn’t in the post, I edit the post if I like the title more. 🙂

  4. Seems like the idea of one theme and maintaining article consistency throughout is really important. I’ve also found that fewer more meaty articles trumps cranking out a large quantity of mediocre posts.

  5. MoneyAhoy says:


    This is great advice. I usually end up changing the title 4-5 times throughout writing an article, but that is mostly to help optimize SEO.

    25 is taking it to a whole new level. It will take a bit longer, but I can definitely see how it will pay dividends in the end 🙂

    • Jim says:

      Once you get into the high-teens and low 20’s, you come up with some crazy ideas and some of them are actually good. 🙂

  6. Morgan Oxley says:

    Thanks Jim, i read all the 24 lists of how to make effective headlines/titles these are all very useful.

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