How to Be a More Prolific Humor Writer, Part 2

Hello again, humor writers. In Part 1 of How to Be a More Prolific Humor Writer, I outlined five interrelated strategies to increase your funny writing output. Think of Part 1 as the core of a humor writing productivity system.

Now, I’ll get into five more stand-alone strategies that will make you so productive that you become a humor-writing demigod. Hyperbole? No. If anything, I’m vastly underselling this (If you’re looking for general humor writing advice, I’ve done that elsewhere).

Could the following advice apply to other forms of writing beyond humor writing? You bet. If you’ve already read Tips 1–5 in Part 1, dive in. Or dive in anyway, because you’re a rebel who hates doing things in order.

6. Join a humor writing group and throw a pitch party

A writing group is a solid tool for being more prolific. You join (or start) a group, then you set regular meetings with routine deadlines for new work. The social pressure of keeping up and not wanting to appear lazy creates a powerful incentive to produce new material. Because clearly, the idea that you’ll die in regret having never written what lies in your soul isn’t motivation enough. We need peer pressure.

But there’s another way to turn your writing group into a comedy generator: Schedule a meeting, or a part of a meeting, where you simply pitch humor piece ideas. Have everyone in your group bring 5 or 10 or 15 pitches. A pitch can be just a headline (a title of a piece), with a clear comedic idea. Here are 3 headline examples from my premise draft list:

• “To Be Happy, Stop Comparing Yourself To Others, Especially Me, Genghis Kahn”

• “How To Convince Your Soulmate That a Threesome Will ‘Strengthen Your Relationship’.”

• “New Gen Z Terminology I Invented To Seem Cool”

Go person by person in the group, and talk about which pitches the group enjoys most. For each good pitch, talk about 3–5 jokes you might write for that piece. You could spend 30 minutes of your 2-hour meeting here, and everyone in the group could leave with a couple of solid, vetted humor piece ideas, along with multiple jokes for each piece. Powerful.

7. Use your inner improv clown to write a “trash draft”

After pitching a comedy premise and waffling about whether I wanted to write it, my friend Ella Gale once told me, “just write a trash draft and see if you like it.” I love the phrase “trash draft.”

“The first draft of anything is crap,” is a writing cliché. But how many of us use that insight to our advantage?

When you write a humor first draft, here’s a helpful mentality to try: “I’m just trying to get the words on the paper. I don’t care about overall coherence or publishable quality at this point.” Lower the stakes by lowering your standards. Yes, your standards for publishable work should be high, but your standards for simply having and testing fun ideas should be much, much lower. Give yourself the freedom to create without judgment.

Similarly, Onion-founder Scott Dikkers distinguishes between Clown Brain and Editor Brain.

Clown Brain is the mode of the circus clown: playful, creative, mischievous, and silly. The clown is never worried about consequences or self-judgment. The clown never runs out of ideas or material because to be a clown is to play in the fully present joy of infinite consciousness and freedom. It’s also the mentality of a good improv comedian, and it is the opposite of anxiety.

Editor Brain is the mode of the editor: nit-picky, scrupulous, judgmental, perfectionist. Editors take wacky ideas, trim every ounce of fat (without stealing the magic that makes them fun), and turn them into publishable comedy gold. Editors are wonderful, necessary people. But when generating ideas and writing trash drafts, editors need to stay the hell away and go clean their pen collections (or whatever they do).

Let yourself be a clown on your first draft. On your second draft, try 50–50 clown-editor. By your third draft, try going full-on editor and sharpen that puppy up. Play around with those ratios.

When you’re an improv clown, you will write many more first drafts. And more first drafts equal more published work in the long run.

8. Explore unfamiliar and uncomfortable topics and formats

I see lots of humor writers who hit the same topic over and over. Dating. Or parenting. Or topical political satire.

It’s natural to “write what you know” and “write what you love” and “write what you love to hate.” Writing within a single niche isn’t a bad habit. It could be a great strategy. It could help you build an audience with people who love that topic, and it could establish your “brand.” All fine things. If you’re doing great within your niche, I say keep at it because I’m a supportive guy, not some internet troll who wants to yell at you for being successful.

However, repeating the same topic can also get boring. And I mean mentally boring from your perspective as a writer. A bored writer is not a prolific writer. If your go-to topics start to feel repetitive, try budgeting 30%-70% of your writing time to work on unfamiliar topics that you’ve never touched before. And if you’ve become stuck and sick of your writing, consider taking a total hiatus — maybe for a few months — from your typical, comfortable topics.

Are your past 15 humor pieces about parenting? It’s time to write about 15th-century pirates, my friend.

Do you always write evergreen humor about aliens and unicorns and never write humor that’s personally or emotionally relevant? Big-time respect, but maybe it’s time to expose your soul and write about one of your insecurities around money, sex, or death.

Push yourself into an uncharted topic and your brain may just say, “This feels new and dangerous. I love it.”

9. Write sequels

Easy rule: If you publish something that gets a strong response from your audience, write a sequel.

A sequel to a humor piece is any new piece that takes the same basic concept or comedic premise as the original and extends it into fresh material with a Part 2, or beyond. Why are sequels so good? Three reasons:

• The comedic premise is already established.

• The premise is already proven to resonate with your audience.

• A comedic tone is already in place.

That’s why a sequel is often easier to write than an original piece. Humor premises are a dime-a-dozen. But excellent humor premises, ones that readers love? Those are much rarer — more like $500-a-dozen. When you hit gold, keep digging.

We’ve used the sequel strategy successfully on Slackjaw numerous times:

• David Attenborough Presents: A Drunken Thirty-Something Female Coming Home Alone (Again), Sequel

• Mid-30s vs. Mid-20s Millennial Men, Sequel

• In Regards To My Recent GoFundMe Campaign To Build A Sex Room In My Garage, Sequel

Here are two pieces I’ve written on Medium that did well enough that I wrote a sequel:

• I Am The One Who Claps Once, Sequel.

• Writers! 34 Things You MUST DO for Your Article to Go Viral!, Sequel.

Both times, I asked myself: “What would be a funny way to keep going with this?” If it’s a listicle (like the 34 Things pieces), just write more list items. If it’s an essay-style article (like the Claps piece), try keeping the same overall premise but give the premise a slight tweak.

A sequel can be a straight-up “Part 2”, but it need not be. You can write a sequel that uses a tweaked but very similar premise, perhaps with a similar joke style or narrator. Here’s an example of both:

• Nihilist Dad Jokes Part 1, Part 2, Part 3. (Same premise.)

• Postmodernist Pirate Jokes (Similar premise.)

Think about your initial, successful premise and ask, “How could this piece be a template for other, similar pieces?” Sometimes, the answer is, “I have no idea” or “I’ve already said what I want to say with this premise.” That’s fine. Not every piece needs a sequel, and it would be foolish to force one when it isn’t warranted. When you publish a banger, simply keep an open mind about whether a sequel is possible.

In the sequel, remember to give ’em more of what they loved about the original. Just don’t make it a boring rehash. While the jokes in your sequel will come from a similar premise, they should feel new. Be sure to throw in a few left-turns and curveballs to keep things surprising and fun.

10. Relinquish envy and criticism of other humor writers

If you want to embody a mentality that makes you as bitter, stuck, and unproductive as possible, try this: Wait until an editor rejects one of your submissions. (It happens to everyone.) Then, when you get the rejection, go ahead and think, “But you published OTHER PIECE X by WRITER JONES THE IDIOT and that piece is not as funny as mine, and I am a better writer than that turd person JONES THE IDIOT.”

To really up the ante, be sure to hit reply and email your inner monologue to the editor who rejected you. This ensures that you’ll squander your precious, finite, irrevocable gift of time by being angry that your ideas didn’t work out.

The alternative is this: Don’t play that game. Don’t torch your energy in the anxiety of comparison and anger. The same goes for leveling social media criticisms of writers you dislike, hating on comedians you find unfunny, and generally acting petty toward people who have more “on paper” success than you — as though you know the first thing about their life or how they’ve struggled.

If you absolutely must indulge yourself and judge the work of another writer, try this phrase: “their stuff isn’t really for me, but good for them.” Think that for about 3 seconds, then move on with your life.

Creativity and humor are infinite. Literally. (I know what both the words “infinite” and “literally” mean because I’ve studied them.) When another writer gets a win, no one has taken anything from you. Nothing is lost. The number of funny ideas waiting to be invented — or discovered, depending on your metaphysics — is the same size today as it was yesterday and the day before: infinite.

Now get out there and write something funny.

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Get The Ultimate Humor Writing Cheat Sheet: my tips and tricks for writing and publishing humor in The New Yorker, McSweeney’s, and Slackjaw.