What I’ve Learned by Running a Humor Site for Six Years
I’ve been a humor writer for eight years, and an editor of a comedy site—Slackjaw on Medium—for six of those years.
This is where I’m supposed to say, “Wow, it feels like only yesterday that I started out as a humorist.” But no, it feels like six to eight long years. Time has passed, subjectively, at precisely the expected rate. Beautiful.
Well, I recently took everything I’ve learned about humor writing and turned it into a book for writers: The Ultimate Guide to Writing a Humor Piece.
In honor of my book launch, here are some themes from the book. Call these my "humor writing aphorisms," gleaned from editing other people's humor writing, being a humor gatekeeper, and trying to make my own comedy as funny as possible.
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A humor piece does best when it hooks the reader with the headline and the first paragraph. You want to grab attention quickly.
To hook the reader means the piece either makes the reader laugh or makes them go, “Whoa, I’m intrigued. Where is this going?”
It’s far more common to overcomplicate a humor piece than under-complicate it. I will often reject a piece for being too complicated or confusing, but I’ve never once rejected a piece for being too simple.
For a piece to be “too confusing” often means: The headline is confusing or unclear, or the piece has more than one main comedic idea.
Can you describe what’s funny about your humor piece in one sentence? If not, it’s probably too complicated or confusing.
A good humor piece is like a good date: by the end, the energy should have shifted a few times.
As more and more people read your satire piece, the probability that at least one person will aggressively misunderstand it and complain about it in the comments section approaches 100%. (This is true even of the most well-crafted satire.)
As a humor editor, even if I reject a piece for whatever reason, few things impress me more than sheer originality, the sense that “this feels new. I haven’t seen this before.”
The 80-20 rule of humor verbosity is this: 80% of humor pieces are 20% too long.
To improve your humor piece, rewrite your piece until every joke is good. Ruthlessly cut jokes that aren’t good.
A good joke always feels fresh and startling. It has an air of something new.
Weird specifics are usually funnier than vague generalities. A character who decorates his apartment with some plants is less interesting than one who decorates it with a Swiss cuckoo clock.
When you include a comedy cliche in your writing—e.g. “Sir, this is a Wendy’s”—a little bit of your soul dies. If you do this enough times, you will have no soul left at all.
Most humor doesn’t escalate enough. How far did you take things? You can probably take the absurdity of your idea even farther still.
One of the easiest ways to make sure all your jokes work is to have a smart person, whose opinion you trust, go through and mark up their favorite and least favorite lines.
When you write a humor piece using a headline that two trustworthy people have already thumbs-upped, your chances of success go up dramatically. Maybe tenfold.
To steadily improve as a humor writer, do this: When you read something funny, stop and ask, “Why was that funny?” Then think hard. When you do that enough times, your comedy brain gets smarter.
Converse law: When you read a bad joke, stop and ask, “Why wasn’t that funny?” Now you’re getting twice as smart.
You can ride the train to crazy town, and the audience will gladly stick along for the ride if you get there with a series of seemingly modest leaps.
Example: “[Consider] Seinfeld, where the situation evolves from something pretty normal to something absurd. Starting the show with Newman trying to eat Kramer like a chicken would be too absurd… But when it comes after a series of steps where Kramer starts shaving with butter, Newman reads a book about cannibalism, and Kramer spills spices on himself, it’s pretty funny.” - humorist Mike Lacher.
Publicly complaining about writing and comedy you don’t like—and shit-talking other writers—is a waste of time. Here’s a phrase for when you encounter bad writing: “It’s not for me.” You can say this quietly in your head and then move on with your life.
First Law of Gatekeepers: They are goalies who help you practice, not obstacles to your dreams.
Second Law of Gatekeepers: They want to accept your work. If they don’t ever accept any work ever, they’re out of a job. Just give them something good.
One of my annoyances in satire writing is when the author is too artless about their subtext. This is the difference between a narrator saying, “I’m rich, and I hate the poor!” versus saying, “Let them eat cake.”
Self-editing your humor writing is a high-value skill and exceedingly hard to master. You can get pretty good pretty fast with outside feedback, but to edit your own work well means you are a vet.
In the weeks you spent agonizing over a humor draft that just doesn’t work, you could’ve written two new pieces that were easy as pie.
Corollary of the preceding: When a draft is hard to crack, stick with it only when you love the idea and the potential is great.
You can’t effectively promote mediocre work. Stuff that doesn’t stand out never goes anywhere, no matter how many times you post it on social media or Reddit.
Truly great humor practically promotes itself. When you write something that shines, it often takes off and people share it.
It’s too hard to tell when a piece will go viral, and it’s a waste of mental energy to try. After you’ve just published something, your best use of mental bandwidth is to immediately work on another draft or five, not waste time checking the stats.
Publishing your humor in big publications is better for your reach and your brag sheet, but self-publishing is better for growing your personal platform long-term. I recommend doing both.
Easy tip to be more prolific: If you write a strong piece, and it gets a good response, try writing a sequel.
Comedy writing is a human skill, and every human skill is improved through deliberate practice. People who say, “you got it or you don’t,” are sad trolls who live out their own limiting beliefs.
Trust your instincts. But keep reading and writing so that your instincts get better.
Humor is both subjective and universal. That’s no contradiction. Some writing is just obviously excellent and will win over your intended audience. And some writing is obviously bad and won’t win over anyone. In the vast spaces in between, there’s plenty of room for disagreement.
If the sentences above help you, great. If not, discard them. You can discover your own aphorisms over time.
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Upgrade your humor writing
Your treasure map to writing killer humor and satire pieces. This is the book I wish I had when I started writing humor.
I also recommend: The Ultimate Humor Writing Cheat Sheet, a 14-page PDF with some of my best humor and satire writing tips and recommended resources. And it’s free!