THE SECRETS OF WRITING ON MEDIUM, PART 3
Put on a Helmet: Let’s Jump Head First into the Uncensored Guide to Writing Headlines
Aardvarks, CoSchedule, and futhorcs, oh my, filled this journey to write a great headline

In my quest to help others become better writers, I tackled the subject of headlines, hoping to avoid a concussion.
Writing headlines is an elite skill. Just hold your favorite newspaper and you’ll find an endless series of terrible puns and bon mots.
It makes me feel so at home.
Before we get into the craft of writing great headlines, I want to warn you serious writers of fiction and poetry about all the articles you see that boast “I made $11,369 this month from writing, and you can, too.”
A brief warning/disclaimer for serious writers.
Before you buy some course that teaches you how to write more effective headlines, please consider this quote that content marketers love.
“On the average, five times as many people read the headline as read the body copy. When you have written your headline, you have spent eighty cents out of your dollar.” — David Ogilvy, advertising legend
Here’s what they don’t tell you…
David Ogilvy RETIRED as chairman of Ogilvy & Mather FORTY FUCKING YEARS BEFORE THE INTERNET became a viable source of video streaming, social media behemoths, and billions of dollars in online ad buys.
If you’re a real writer, please know that Ogilvy was talking about the advertisements appearing in newspapers, magazines, radio, and TV, and has nothing to do with the true value of your book.
80% of the value of your book is not contained in a headline.
Now, back to the specific importance of headlines for writing short articles on Medium.
In the cold, cruel world of digital writing, the headline is a link, and a writer’s livelihood depends on getting people to click before they can read the initial copy.
This is why the term “clickbait” has entered the English language.
It is why you will find a million articles about writing headlines on Medium. If you don’t believe me, just type in “writing headlines” in your search box.
[UPDATE: I was completely wrong about the million articles about writing headlines on Medium — I stopped scrolling after a hundred. There’s no way to know how deep the hole goes unless you’re even more willing to waste your time than I am. What I will say is that Google gave me 216,000,000 results for “writing headlines.”]
Some content marketers talk about spending hours reworking their headlines — could it be that the rest of their articles are just regurgitated quotes from more famous people and generalized babbling?
Still others approach writing headlines (and data driven content) with such cynicism, it’s almost criminal. Oh wait… that was me.
However, I do recognize the importance of writing better headlines if you’re trying to build your audience as a blogger, and that is the goal of this story.
Since I know nothing about writing headlines (as evidenced by my virtual anonymity), I decided to do some serious research.
In this cool article, Dave Schools taught me a lot about writing headlines. He presented the work of data analysts who went through 100 million headlines of articles shared on social media. Here’s a gem on how to start your headline:

My takeaways from his article:
- Never start a headline with a gerund, i.e. “Doing This Will Get You Thrown Off Medium.”
- Of the top 20 first words used in headlines, 9 of them are numbers. You will bow to the listicle.
- How, What, and Why are all in the top 6 most used first words in headlines. Is there a question here?
- “This” and “Trump” are can’t miss words to use in my super duper-headline that will surely attract millions of readers.
- Other good words in the top 20 to use are “You,” and “After.” (In retrospect, I should have focused on “New” and “No.”)
Here are my other observations after reading every headline by the most successful writer on Medium:
- Use power words like “Success.” He used the word 22 times in his headlines over the last couple of years.
- Stay positive and try not to lie. For example, when you read those articles that say “and you can, too,” they will tell you everything involved in their writing process, while conveniently omitting everything they do in the marketing process. Remember, if you can build a base of at least 4,000 followers, you only need 5% of your fans to clap 10 times each for an article to be in the top 1% of Medium. (Ca-Ching!)
I applied everything I learned from headline writing articles and slaved for hours to craft the headline below.
My strategy was to combine as many of the top first words from the list as possible and throw in the word “success” twice because it is so powerful.
Behold this beauty:
This is What Trumps All: How You Become a Successful Writer on Medium in 5 “Anything is Possible” Steps. After… Success!
But how do I test the effectiveness of my headline?
In another article, a helpful writing coach (not a shyster content marketer) offered this resource: #1 Free Headline Online Analyzer.
After a long sign-up process where I submitted all my business information so the company could harass me until the end of the millennium, I submitted my headline and held my breath.
My score was 64 out of 100.
And here I thought I sucked at writing headlines.
(Note: Before you laugh at my efforts, try out the above site and see how your own headlines score. I’ve tested headlines from some of the most popular writers on Medium, and you’d be surprised how many seemingly good headlines don’t even break 60.)
According to the writing coach, I needed to try to rework my headline until I got a score of at least 73.
And so, the journey begins.
To make it easier to track the evolution of my headline, I formatted the keyword changes in bold for easier reading.
Here is the revision history of my headline:
- (Removed first clause) How you become a successful writer on medium in 5 anything is possible steps. after… success! — 52. My score dropped by 12 points in getting rid of Trump. WTF?
- This is What Trumps All: How You Become a Successful Writer on Medium in 5 “Anything is Possible” Steps. (Removed last clause) — 61. My score dropped when I deleted “After, Success!” I’m lost.
- This is What Trumps All: How You Become a Successful Writer on Medium in 5 Easy Steps. After… Success! — 69! That first lie really helped!
- This is What Trumps All: How You Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! — 73!! Two lies are better than one. Why stop now?
- This is What Trumps All: How You Become an Unstoppable Writing Force on Medium in 5 Simple and Easy Steps. After… Success! — 70. Note to self: Success is more powerful than unstoppable.
- This is What Trumps All: How You Become a Successful Writer who Succeeds on Medium in 5 Simple and Easy Steps. After… Success! — 73. The redundancy did not help at all. I need to find a new lie.
- This is What Trumps All: How You Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success… and You Can Too! — 73. It works for everyone else, but not me.
- These Secrets are What Trumps All: How You Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! — 68. Secrets are not sexier than “this.” What am I doing wrong?
- This is What Trumps All: How You Can Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! — 73! Why stop now?” — 76!!! just to be clear, I accidentally copied and pasted “ — 73! Why stop now?” and my score went up to 76. Even my typos are better than anything I try to write seriously.
- This is What Trumps All: How You Can Become a Successful Writer NOW on Medium in 5 Simple and Easy Steps. After… Success! (Removed last clause) — 75. Apparently, applying the rules of grammar and brevity have no place here.
- This is What Trumps All: How You Can Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! Why stop now Aardvark? — 76. Okay, aardvarks are not effective content marketers.
- This Linguistic Paradigm is What Trumps All: How You Can Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! (Removed last clause) — 71. Linguistic Paradigm did nothing to score in the categories of “Uncommon,” “Emotional,” and “Power.”
- This is What Trumps All: How You Can Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! Why stop now? Thousands can’t be wrong! — 77!!! Can you feel the power of that extra lie?
- This is What Trumps All: How You Can Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! Why stop now? 1,000s of entrepreneurs can’t be wrong! — 78. Holy Shit! I’m reaching the holy grail!
- This is What Trumps All: How You Can Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! Why stop now? 1,000s of successful wordsmiths can’t be wrong! — 78. It didn’t change the score, but Wordsmith is more appealing for our audience of desperate Medium users. What’s next?
- This is What Trumps All: How You Can Transform into a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! Why stop now? 1,000s of Successful Wordsmiths Can’t be Wrong! — 77. Become is stronger than Transform.
- This is What Trumps All: How You Can Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! Why stop now? 2,769 successful wordsmiths can’t be wrong! — 77. A larger number did not work.
- This is What Trumps All: How You Can Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! Why stop now? 525 successful wordsmiths can’t be wrong! — 77. A smaller number did not work. Is it even versus odd numbers that could do the trick?
- This is What Trumps All: How You Can Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! Why stop now? 10 Successful Wordsmiths Can’t be Wrong! — 77. Still no luck. What am I missing?
- This is What Trumps All: How You Can Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! Why stop now? 1000s of Successful Wordsmiths Who Are Successful Can’t be Wrong! — 79!!! I’m almost at the summit.
- Successful Success Succeeds Like No Other Writing Skill on Medium. 1000s of Successful Wordsmiths Who Are Successful Can’t be Wrong! (Removed last 2 clauses) — 53. It was arrogant of me to try to clean this up. Lies and typos have far more skill than I do. Also, I guess you can be too successful. The analyzer is saying I need more “uncommon” words.
Hearing me cry with laughter, my son came to the rescue.
He began to search for some uncommon words.
- This is What Trumps All: How You Can Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! Why stop now? 1000s of Successful Wordsmiths Who Are Successful Can’t be Wrong! Genipap — 79. Genipap is not “uncommon.”
I thought, maybe using a more flowery word for writing would help.
- This is What Trumps All: How You Can Pen Successful Articles on Medium in 5 Simple and Easy Steps. After… Success! Why stop now? 1000s of Successful Wordsmiths Who Are Successful Can’t be Wrong! — 78. The active verb “pen” had no effect.
Then, my son added one final phrase.
- This is What Trumps All: How You Can Become a Successful Writer on Medium in 5 Simple and Easy Steps. After… Success! Why stop now? 1000s of Successful Wordsmiths Who Are Successful Can’t be Wrong! Know Your Futhorc. — 81!!!
And, send to print.
I hope you enjoyed this journey as much as we did.
Look for this headline in my next article on writing.
[UPDATE: I am excited to announce that my deep research into writing headlines has resulted in Medium’s curator selecting one of my writing rants in the writing category at 1:03 AM PDT.
The winning headline was “An Open Letter to Writers Who Write to Other Writers About Writing.”
My headline received the red carpet treatment with a triumphant 50 and…

I’ve been reminded that the scale is 50 out of 100, so now I have no idea why this happened, let alone who would be up at 4:03 AM in New York curating articles. My only guess is talking about walking my dogs must have scored points with those Corgis hard at work.]
Here’s a screen shot to prove it happened, just in case they realize their error and remove the story.

Thanks for reading, sharing and commenting. If you want to be tortured further, here are parts 1 and 2 of this series.






