How One Headline Brought Me 99 New Subscribers
This is NOT a humble-brag, it's a tool you can use to improve your headline-writing skills.
This is a repurposed version of one of my all-time most popular posts from last year.
I LOVE sharing free tools with writers who may find them helpful!
If I had to pick the one comment Iβve heard most from readers (besides raving about my idea-weaving brain), itβs about my headlines. And itβs been happening since long before Substack:
How much thought do you put into your post titles?
Are they general and vague? If so, do you hope to draw readers in with it? This isn't Tinder. People should not be yawning and swiping LEFT on your posts.
I recall coming across a blog post titled βMom.β Iβm sure Iβd love your mom, but how are you convincing me to read her story with a dull headline like that?
If you call your story βCats,β I may block you because I donβt like cats π However, if you call it something like βYour Cat Does Not Belong On The Dining Room Table,β Iβll dive into it headfirst because I wholeheartedly agree they donβt belong there.
(BTW, that cat story by Roz Warren went completely viral on Medium and the whole internet. See what Iβm saying?)
While writing coaches everywhere are ranting at you about writing good headlines, nobody is telling you how to KNOW if itβs a good headline.
Hereβs a FREE tool to help you:
Iβve used it for every single headline I've written on three different Substack publications and for many years over on Medium.
Itβs called Monster Headline Analyzer.
Iβm sure itβs not the only headline analyzer on the internet, but Iβve been using it forever, and I consistently receive amazing feedback, so thereβs that.
To illustrate how I put it into practice, hereβs a screenshot of several headline possibilities I tried for this exact post last year.

And here are the stats from this post last year:
When you type a title idea into this tool, it rates it on a scale of 0 to 100. Look at the significant difference a word or two can make in that screenshot above.
This headline tool doesnβt only give you a numeric score; it provides a whole page of advice, ideas, word suggestions, and more to help you improve your headline. If you consistently use this tool, eventually you will learn the key elements of a great headline.
I love challenging myself to come up with titles scoring 90 or above. It has become a game of running random sentences through this tool to generate possible story ideas, including the one youβre currently reading.
See how adding ONE word changes the score dramatically?
I am now using this post as an A/B split test because itβs the same one I published a year ago, but with a different headline. The only difference this year is that I have almost four times the number of subscribers. So, letβs see how this plays out.
Never be afraid to experiment!
DISCLAIMER: The tool cannot teach you how to be funny, witty, or creative. πHowever, it can teach you how to be concise while offering alternative ways to craft your perfect headline.
Youβre welcome! π
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Interesting I ran my highest ranked / read posts thru the analyzer and they got low scores - I wonder if it rewards click baitey titles over more soulful and nuanced ones?
Writing strong and catchy headlines is something that has eluded me. Thank you for this post, the tips and tools - I needed them!