That Time I Earned $1,586.00 From One Viral Medium Article
4 key takeaways I learned from milking my post-50 dating escapades here on this platform

Some people loved it. Some people hated it! I dug deep and told a story from the heart. From my guts. It was a story of my post-divorce sexcapades. A comic tale of unrequited lust. I hit publish on a tiny pub on Medium. The next day I woke up and my story was doing business. Soon it would go viral. Oh what a feeling!
Five months later, somehow this story is still in people’s feeds and is racking up views.


As you can see in the screenshot, there was that first big bump at the time of distribution. But then it became the Little Story That Could. It was still going very strong in August. September took a dip, but October was decent and November was a little more of a surge. The story of this article, unlike any of my others, is longevity.
I’m sorry Ash Jarburg, I can feel you cringing across the Internet. I really do admire you and I know how you hate these meta articles, but here I am writing an article about my Medium success.
I do so because I hope to inspire and enlighten all of you writers out there who want to go viral in the best sense of the word, not in the kind that requires popping hydroxychloroquine and ingesting bleach.
So, these are my 4 key takeaways from going viral.
1. Deliver on the movie poster
The royalty-free image or original artwork you choose to feature underneath your headline is your movie poster. From my experience as a screenwriter I can tell you that in order to please your audience, you’ve got to deliver on the promise of the premise.
When the audience sees a movie poster that shows Anne Bancroft rolling a sheer black stocking up her sexy dancer’s leg as an adorable deadpan yet near- drooling 21-year-old Dustin Hoffman ogles her from the doorway, you’re already in love with Mrs. Robinson too.
But if this tantalizing relationship was never consummated in the film the Graduate, you’d be as frustrated as Benjamin is when he realizes he’s blown it with Mrs. Robinson’s daughter, Elaine. There are dozens of reasons why this is an iconic, amazing film, and one of them is that the audience came in wanting to get the experience promised by the poster, and boy did they ever.
As for me and my humble story?
The photo shows a sexy, half-clad woman getting ready to get massaged by a hot guy who is about to pour warm massage oil on her bare back. Now if this turned out to be a story about oil or towels or massage tables, the readers would scratch their heads and say, WTF? Where’s the hot guy? What happened with this woman? The headline says, That Time I Came On To My Masseur. I hate the term cougar but yeah, I went to Cougartown.
Oh man, we want to see her go to Cougartown! And she/I did! So I effectively delivered on the promise of the premise. Which leads to #2:
2. Spend as much time on your headline as you do writing your story
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.
Those smart words were spoken by the famous advertising revolutionary, David Ogilvy.
A great headline does three things.
It makes you want to read the story
Example: First Try the Pastrami, Then the Polyamory.
OK, I’m in. I can’t not read this story! I’ve actually read it a dozen times, that’s how good it is.
Stephanie Gruner Buckley’s first Medium story went viral. When you read the headline, you can understand why: My daughter was a creative genius, and then we bought her an iPhone. Wow.
It promises to solve a problem you can relate to
Here’s a few examples:
The Emotional Toll of Enduring Anti-Asian Attacks
Anxiety Is in Your Body, Not Your Mind
Amazon’s Dark Secret: It Has Failed to Protect Your Data. Voyeurs. Sabotaged accounts. Backdoor schemes. For years, the retail giant has handled your information less carefully than it handles your packages.
It evokes, provokes, and/or intrigues
Example, from Your Tango, a relationship site, How to Keep Your Sex Life From Drying Up After You Turn 50. Wow, this is an evocative and provocative headline. I might want to read it because it’s intriguing, and of course, I don’t want my sex life to dry up! So I’m compelled to read the piece, which goes back to promising to solve a problem you can relate to.
Here’s another one: Dad Angry At Mom For Waxing 5-Year-Old Daughter’s Unibrow To Protect Her From Bullying. I mean talk about specificity, right?! You’ve got a lot going on here to learn about — parenting, ethics, bullying, culture, etc. You’re dying to read on.
You may be wondering:
What is the difference between a provocative headline and clickbait?
Is my Masseur headline clickbait-y? No. It’s provocative, it’s sexy, it’s intriguing, but it doesn’t fall into the clickbait realm. Clickbait is false advertising, and Medium has stated that they frown on clickbait.
Clickbait is content that’s designed to entice a reader to click. It often shows up in the form of deceptive or manipulative story packaging — a hyperbolic claim, a too-wide curiosity gap, a titillating image, etc. These stories do not follow through on their promise and often leave the reader unsatisfied.
For example, if you have a listicle and in the subtitle of your headline you proclaim, #6 is gonna blow your mind! Yet it’s a fluffy piece with no new and riveting information and #6 blows no minds, you’ve now lied to people. You’ve lost your audience and damaged your reputation.
This is a great resource I have leaned on— it’s an article titled, 5 Data Insights into the Headlines Readers Click. It goes into detail about the type of content that gets clicks and why. Check it out — there are a lot of helpful stats and suggestions that will steer your content creation and help it stand out.
3. Research and choose your publication wisely
I published that viral story in a smaller humor publication on Medium called Humor Me. Is it the largest humor publication on Medium? No, it is not. Slackjaw is the biggest, with 107k followers. But they are a hard nut to crack, they also have a very specific vibe and not every humor piece is going to be a fit for Slackjaw.
Also, bigger isn’t always better (please, get your mind out of the gutter). I have published in some of the larger pubs on Medium and there is definitely no guarantee of virality just by getting accepted into a large pub.
Humor Me is a tiny pub. I am having a hard time finding out how many followers they actually have (if you know, please do write in the comments). I’m not even sure how I found them, I think I just liked one of their articles and submitted to be a writer there.
It turns out there are significant benefits to publishing in a smaller pub. For one thing, they are very niched down. Whereas the Startup may publish stories that cast a wide net of subjects, smaller pubs are very specific. Their content is targeted to the wants and needs of their readers. Followers may be a smaller lot, but much more engaged.
Humor Me’s tone and style suited my piece particularly well. Their confessional headlines all start with “The Time” or “That Time” which is a brilliant device that immediately draws the reader into your world, your unique story, your crazy experience, your sexcapade-gone-wrong.
I don’t remember what my original headline was, but happily, I had to change it to “That Time I…” per the publications requirements, so the headline was perfect. It was enticing, funny in a self-deprecating way, and lured the people right on in.
But the real key to the success of this piece is in #4…
4. The Little $1,549.00 Tag That Could
I have two Medium accounts which I sporadically write under. Maddie is a pen name. She writes about what it’s like trying to go up against a narcissist in divorce court. She writes no-holds-barred fun and sexy NSFW stuff.
She/I/we have written dozens of articles, but I was actually completely stumped at the success of this piece. Yes, I did have hella fun writing it and I knew it was a solid piece of work. But many of my other articles are good and they don’t get nearly the action this one is getting.
So in November, when I received a $229 November payment for this story which was written back in July I thought, how the F. did I do that, and how the F. can I get that lightning to strike again?
I decided to ask Tom.
I recently signed up for a course by a lovely Medium sherpa named Tom. I figured since I subscribe to Tom’s awesome newsletter and now am taking his course, he might enlighten me as to how this piece is still discoverable, attracting reads, comments, likes, and subscribers 5 months on. This is when Tom enlightened me:
Here take a look at this page: https://medium.com/tag/this-happened-to-me/top/year
If you scroll down, you’ll see your story is listed there as one of the best stories in the “this happened to me” tag for the year. Pretty awesome stuff! I don’t think people are discovering your story from this page, but I do think that people who follow that tag are likely getting your story on their homepage. What other tags was this story tagged with? You are probably trending in those tags too.
I was amazed to learn this tidbit! Back when I wrote the story last summer, I had been researching intentional, smart tagging on Medium and I liked the confessional “this happened to me” tag. Is it the tag most commonly used on Medium? No, and that is not necessarily what you’re going for with tags.
When I research this tag now by entering, “https://medium.com/tag/this-happened-to-me,” I can see there are 31k stories that use this tag, and 7.7k writers using this tag.
I could have used the tag, “life” which is currently used in 594k stories and has 175k writers. But imagine the competition to rank as one of the best stories of the year in this tag? It’s up there with winning the Medium Writer’s Contest. In other words, it’s near impossible.
But, now that I have gone and said that, I found this link, “https://medium.com/humor-me/tagged/life” and on the page of Humor Me stories tagged “life,” mine is the third one down!
I also realized tonight as I was researching this article that this link, their about page, “https://medium.com/humor-me/about” shows the editors and writers, and there I am, listed on the first page! Bonus time! I heart Humor Me!
So the lesson here is this: going down a rabbit hole and researching what smart Medium gurus like Zulie Rane, Casey Botticello, and Tom Kuegler have written about tagging will serve you well in creating work that will stand out, get curated, get reads, and earn money.
To sum it up, I put a lot of thought into the photos/illustrations I use. I have spent hours poring over images on Shutterstock, a service I highly recommend, picking the one that perfectly expresses what the article is about visually. I write my headline down and continually glance at it while I’m scrolling through images so I can nail the emotion and overall vibe of the piece. I always end up going with my gut.
I have spent hours researching how tags and curation work on Medium.
I often spend a long time writing a piece, and the next day, I edit. Then I edit again. Then, when my eyes are starting to bleed, I reread. I manage to catch new edits.
I spend an inordinate amount of time laboring over my headlines. Success on this platform has been a learning curve over the course of a year plus. Every day since I published the Masseur article I have a green circle showing engagement, claps, comments, and follows. I love that green circle of life!
Putting all of these elements together was not an overnight process, but it paid off in spades and inspired me to double down on my efforts to write and succeed on this platform. I hope my story inspires you to do the same.
Walk with me through midlife — sign up for my newsletter here. Let’s leave our baggage behind and steal those warm nuts from first class.






