Experiment More

Plus, reader questions about joke writing and moving on from bad drafts.

Most humor writers don’t experiment enough.

We are too liable to stick to what’s familiar and comfortable, continually greasing the groove.

You should get out of that groove from time to time.

How?

• Publish in a humor format you’ve never tried before.

• Write in a voice that feels weird or experimental.

• Take a point-of-view, or argue for a subtext, that feels strange.

• Write about a subject that you’ve never written about before, maybe one that you know very little about.

• Just do something new, dammit.

Experimentation is healthy. It can lead to lovely discoveries. You can learn from experimentation.

Also, experimentation in humor writing costs almost nothing. You’re not a pop star. You’re not the Weeknd. No one demands that you deliver dark, moody, and cinematic R&B.

You’re free. No one expects anything. You can write something offbeat and totally different and none of your readers will say, “Ah, but I really wanted a satirical listicle about how healthcare is frustrating. That’s what I expect from you, writer. I am disappointed!!”

You have a self-publishing outlet, right? Every humor writer should have a Medium account, or a free Substack, or a blog on a YourName.com domain.

Write something different, maybe something kind of insane. Do it just this once, and throw it on your blog.

I dare you.

---

Reader question: When and how to move on when a piece isn’t working

“Here's a question for ya: What are some ways to know when a piece just isn't working, and may never work, no matter how many revs or readers it goes through? Do you have suggestions on how to move on, when the piece is something we may have worked on for a long time?” - Leanne

The quick answer is that I would give it three drafts. If your piece is not getting funnier and making appreciable progress towards the finish line, within three drafts, I’d shelve it.

But moving beyond that quick rule, here are some other questions to ask yourself: