How to Be a More Prolific Humor Writer

Nov 26

Welcome, humor writers and aspiring ones. Do you want to increase your funny writing output? You’re in the right place.

(If you’re looking for general humor writing advice, I’ve done that elsewhere.)

Here, I’ll focus on five writing practices that have helped me write and publish more humor.

1. Write from a headline or premise, not a blank page

When you write a humor piece from a blank page with no idea of what you’re trying to accomplish, you face an unnecessary uphill battle. You will waste countless hours dinking and derping around trying to figure out what you’re writing about and what’s funny about it.

Short-form humor works best when the main funny thing is obvious, to both the reader and the writer, from the start. That’s why it’s more efficient to start with your premise. And when I say a “premise” or “headline,” I mean a funny or exciting title for your humor piece or a concise description of what the main funny idea is. Here are three premise examples:

In each case, I wrote the title first. Once I knew the funny idea, my job was easier; I just had to explore and heighten it within 800 words.

The premise-first approach applies to conceptual short humor pieces, like the stuff above, but it works well for other forms of humor writing like humorous personal essays.

2. Work on your list of headline/premise ideas constantly

The more funny ideas at your disposal, the more prolific you’ll become. That’s because a good humor concept is half the battle — or maybe a quarter to three-quarters. I do a few things to grow my list:

I take specific chunks of time in my writing schedule solely to work on writing new humor premises.
I keep my running list of premise ideas handy in a notes file that’s accessible from my phone or laptop. If a new idea hits me, I write it down immediately. Never waste a good writing idea or a solid joke by forgetting to write it down!
I don’t worry about making all of my ideas incredible. That’s too hard. I just write a lot of them and pick the best ones later. As Onion founder Scott Dikkers teaches, quantity produces quality.

When you have a running and growing list of humor ideas, you’re never at a loss for something to write. In picking your next piece, you want to face an embarrassment of riches, not an agonizing blank canvas.

3. Work on multiple pieces at once

I write several pieces at once. If and when I get momentarily stuck or bored with one humor article, I pivot to one of my other active pieces. This prevents dead time and means I always have momentum on an exciting piece.

My personal sweet spot is three to five pieces at a time. Fewer than three, and the risk of getting stuck increases. More than five or six feels overwhelming to me. This doesn’t mean I’m literally working on all of these pieces every day. It just means that these are my “active” pieces that I intend to work on in the coming weeks.

Literal multi-tasking in real-time is awful for human brains, so I avoid that. Within any given writing session, I focus entirely on one piece. Unless I get stuck. Then I switch pieces, and I focus entirely on the new piece. The lesson here is don’t force your brain to be a linear assembly line when it doesn’t want to be one.

4. Have a writing-publishing system

What’s up, nerds: Having an organized writing system that suits your idiosyncrasies and your ideal workflow will help you. Here’s how I organize my humor writing. This organization is what works for me. Each of these is just a folder full of text files.

Writing — Working: This is my folder for pieces I am actively writing. Typically 3 to 5 humor pieces, plus (possibly) some other stuff like fiction or essays.

Writing — Hibernating: This is where I keep all the pieces that I think have some promise, but I am not actively working on them. I like everything in this folder, and while I don’t want to lose this stuff, I also don’t want to look at any of it right now. “Out of sight, out of mind,” as the thought-leaders say. I might keep 20 or more pieces here at any given time. I review this folder at least every few months, visually scan each piece and decide whether to keep it in here, bump it into “Active / Working” status, or send it to the graveyard.

Writing — Graveyard: These are all of my unfinished pieces, or failed drafts, that I don’t want to publish or work on anymore. Why not just delete? You could. However, having this folder tells my brain, “Hey, it’s fine to give up on this piece. See, look, we’re not even deleting it! We’re just storing it in the graveyard. Calm down, brain.” Death is natural, and a graveyard is a good thing. If you’re not killing lots of ideas, you’re probably being too precious or timid with your writing, or you’re just not writing enough.

Writing — Ready: My finished but unpublished pieces. I keep them in one spot so I’ll remember to get them out there in the world.

Writing — Published: My published stuff, for reference. I can glance here when I’m feeling a little discouraged and pump myself up: “See, look! Past Me wasn’t a failure!”

You are welcome to copy my system, and if so, you owe me $30.

5. Don’t burn time on pieces that aren’t working or aren’t fun

Humor writing is not a natural activity. It won’t always be easy. Yes, very occasionally, you will have a premise that’s so good that “it writes itself.” Then you write the piece in an hour, publish it immediately, it goes viral, and a hot Swedish model approaches you on the street and says, “I read your funny article on Medium. You are amazing. Will you go on a date?” That’s awesome but rare. It’s only happened to me four times.

You will get stuck a lot, I promise. When I get stuck, I ask myself: “Is this a great premise, but I’m just having trouble executing it right now? Or is this piece just not working at all?”

If the former, that’s fine. I set the piece aside and work on a different one. Or, if I’ve been stuck for a while, I put it in hibernation, and I focus elsewhere for a month or three.

If the latter (the piece isn’t working at all), that’s also fine. I send it to the graveyard and don’t think about it again. It can be tough to do this, but sometimes it’s necessary.

Time is finite. When you have a great list of humor ideas, you don’t need to waste time on one that doesn’t love you. It’s tough to decide when to persist, re-write, and struggle to the finish line versus giving up and trashing the draft. I’ve learned this mostly by trial-and-error. You just have to hone your gut over time. Let’s sum up:

Cultivate your list of humor premise ideas, and water it regularly.
Draft your piece using ideas from that list, not a blank page.
Consider working on a few pieces at once (whatever number feels right for you).
When a piece isn’t working, don’t suffer. Put it away and work on something else.
Spend as much time as possible on humor ideas that are working and excite you now.

If you do all of that, I guarantee you’ll be a more prolific humorist, and a “BOOM” sound-effect will materialize over your keyboard like in a Batman cartoon.

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Alex Baia