What I Learned From Publishing 100 Comedy Pieces on Medium
On hitting the Mach 1 of humor writing
In the eighth grade, I had an eccentric math teacher that everyone called “Mr. O.” His actual last name was Polish, and very long, and very hard to pronounce. So Mister O it was.
Mr. O was perhaps in his sixties then, although to my young mind he seemed both impossibly ancient and basically eternal.
Mr. O had a PhD in mathematics—I believe from the University of Warsaw— and an impressively quick and encyclopedic brain that can only come from a dedication to studying hard, technical knowledge.
Mr. O was a character: he always wore a pristine suit to class, with a Rolex watch. He adopted all kinds of odd and endearing mannerisms and class customs, like throwing foam balls around the class, and giving bonus points to students who answered especially hard problems and extra bonus points to students who answered a problem that another student had failed to answer. (The latter students he called “vultures,” as an honorific, in the most hilarious and thick accent, and I can hear the way he said “vultures” crisply in my mind’s ear to this day.)
Mr O. was also a holocaust survivor who had been shot at and nearly buried alive by Nazis when he was a boy, and he managed to escape a death camp and eventually find his way to earning a doctorate in Poland and teaching math to middle schoolers in Colorado.
That sounds kind of sensationalist and attention-grabbing to say, but it’s true, and it feels like an important part of Mr. O.
We loved Mr. O. Every last one of us. His intelligence and aura was fierce.
Mr. O had a saying that always stuck with me.
“You’ve hit the Mach 1 of mathematics.”
He maintained that if you wanted to be good at math, you should solve 100 homework problems per night.
One hundred. Per night.
Good lord.
And if you could hit 100, then, you were a champ, the Chuck Yeager of middle school math.
The idea of doing 100 of something worthwhile always stuck with me, thanks to Mr. O.
And I think there’s something to it.
If you want to be good at writing personal essays, write 100 of them.
Good at stories? 100.
I’m talking about any writing endeavor that takes pretty decent craft and mental effort: not as much effort as writing a 250-page novel, obviously, but much harder than writing an email.
So, whatever you’re writing: do that 100 times, and, if you’re pushing yourself, you can’t help but get better at it.
100 humor pieces would be the “Mach 1 of humor.”
And so, I thought of Mr. O recently when I realized that I had self-published more than 100 comedy pieces on Medium—on Slackjaw, specifically.
So, that’s all a long preamble to saying: I couldn’t do it in one night, but I hit my 100 nonetheless, sir.
This one’s for you, Mr. O.
I joined Medium and started publishing there in 2018, shortly after discovering Slackjaw.
At the time, I was pretty new to writing, and I had published a few things in McSweeney’s and a few things at some other humor sites, but I was pretty green still.
Medium (and Slackjaw) seemed like this cool outlet for fresh and humorous writing.
The appeal was that they would be not quite as picky as the notoriously picky McSweeney’s, and I could grow a bit of an audience there, and it was a different vibe than trying to publish something in a mainstream site or a literary pub.
Aside from some craft essays I wrote for The Writing Cooperative over the years, the majority of what I’ve written on Medium has been comedy pieces and short stories on Slackjaw.
Not sure when I officially passed the 100 humor pieces mark, but it was recently.
(I’m only including pieces I “self-published” after becoming a Slackjaw editor. If I include the handful of pieces I published on Slackjaw before I was an editor—which I submitted to the inbox like anyone else—I guess the total is around 107 or so.)
Regardless, Medium has been immensely valuable to me to as a humor writer.
Self-publishing my humor on Medium has allowed me to experiment, learn a lot, grow an audience, and even make some grocery money.
Because those 100 comedy pieces have been a significant part of my writing journey, I’d thought I’d try to sum up what I’ve realized about all of it.
(Side note: I wrote a longer deep dive on Medium vs. Substack here…)
Boiling it down, the value of Medium, to me, has been five-fold:
Working my chops through volume
Stylistic experimentation
Audience building
Making money
Finding friends and collaborators
Are those all of the benefits? I think so. I don’t think I’m missing any!
My personal favorite pieces from the 100
Before I get to all that, here are my favorite dozen-ish comedy things I published on Medium over the years.
Are these the pieces that taught me the most? That got the most reads? That made the most money? Not necessarily. These are just personal favorites.
Three Habits To Give Up Today If You Want To Stop Being Mauled By Bears
You Look Weak My Dear Boy! We Must Feed You These 9 Suppers At Once!
(I might rank this as my personal #1 fave)7 Quotes From Stoic Philosophers That Made Me Lose My Goddamn Mind
Your Dating Profile Works Best If You Lead With Anger And Bitterness
Every Day We Must Ask, “What The Fuck Is This Shit?” With Compassion And Mindfulness
What I, An American, Will Say To The Clueless Europeans Who Visit My Country
Listen, Kid, Being An Adult Is Harder Than You Can Possibly Imagine
Working the writing chops through volume
One of the great joys of Medium is that it lets you publish with nearly zero friction.
You don’t need to do anything special to publish your work. You get a free account in sixty seconds, and you can just immediately create a post and make it live on the web.
There’s a lot to be said for minimizing creative friction to the bare minimum.
You can just focus on writing.
You don’t need a special blog or any infrastructure that you have to keep up.
No personal website or email list or social media following required.
You don’t have to promote your work if you don’t want to. Of course, many Medium writers do, but you need not: you can just write and publish, and Medium has a built in audience of millions of readers (including over 1 million paying members), who might read your self-published story.
Will any of those readers actually read your story? Ha ha! Probably not, at least not right away. But if you write something truly good, your story could fly.
You can also submit your story to a Medium publication for slightly higher reach, but you don’t have to do that. You can just self-publish to your profile, and your story goes live to the web and to the Medium ecosystem.
Side note: Yes, I published these 100 comedy pieces on Slackjaw, a site with a following on Medium. All of the Slackjaw editors, being unpaid volunteers, have this as our bit of compensation: being able to publish to Slackjaw as much as we like, no restrictions.
But that doesn’t matter all that much for the points I’m making here. What I’m saying here applies equally if you simply self-publish on Medium without any editor approval.
Publishing without asking permission is, I think, a cornerstone of working your chops with the lowest friction.
Sure, you can just write something and save it to your laptop, and, yes, then, you’ve worked your chops, but what’s the fun in that?
Publishing it live to the internet makes it real. It’s out there for anyone to read.
Experimentation
All artists should play around. A lot. This is for a few reasons.