I wish I could sit down and totally nail a first draft. But the truth is that almost all of my humor pieces (at least 95% of them) started out as something completely different. It’s not a very efficient way to work, but that’s how it goes for me. I have to try an approach, realize it’s not quite right, then try it a different way.
Of course, moving on from that first (or second, or fifteenth) draft can be hard. But I think, if you sense that something isn’t quite right or you’re running out of steam on a piece, that it often saves you time to write a new draft with a different angle or format.
In the spirit of proving that thesis, I thought I’d share some before-and-afters of ideas that didn’t work the first time, and how I eventually got them to work.
The piece: Modern Love Essays By Nursery Rhyme Characters
The pivot: This was originally a monologue before it was a list.
The backstory:
Though it ended up as a parody of Modern Love, that wasn’t the initial inspiration. The original headline was “Peter Piper Picked A Peck Of Pickled Peppers Instead Of Going To My Birthday Party.” The game of the piece was around the idea of being in love with a guy who only has room in his life for peppers.
The piece went through so many iterations, and at one point I was trying to weave in as many words that started with P as possible, hoping that would unlock the comedy (it did not).
Eventually, since it was about love, I thought it could work as a Modern Love parody. To make it sound more like a Modern Love piece, I re-wrote the title as, “I Picked Him. He Picked Peppers.” But I was still trying to make it work as a parody of an essay, and it wasn’t working. So I shelved it.
A few years later, I looked at it again and realized: “Actually, what’s funny about this piece is just the title of the essay itself.” I realized that different Modern Love essay titles based on nursery rhymes could be the entire piece. The list version of the piece was super easy, fun, and quick to write. After I finished it, I reached out to the incredibly talented Ali Solomon to see if she’d be interested in illustrating it, and voilà.
The piece: I’m a Driver in a Subaru Commercial. Please Send Help.
The pivot: This was originally a list before it was a monologue.
The backstory:
I wrote this piece because I was getting ready to join a writing group, and the idea behind the writing group was that we’d share one piece a week. I immediately panicked because I had no new ideas. So, I went through my long list of premises and random bits and bops, and I found a piece I had started writing years before. I had a bunch of alt titles for it, but one title was, “The Person Car Commercials Are Targeting.” A few of the initial reps were:
Lives on top of a snow covered mountain
Enjoys big red bows
Likes to surf
Often drives through desert terrain
Has exactly four hot young friends who love to smile
When I was re-reading it, I realized it would work better as a monologue. I wrote the idea down as, “It’s someone ranting about their four hot besties always hitting them up for rides, and how they live on top of a snow-covered mountain so it takes them forever to get anywhere, and the only thing they enjoy doing to blow off steam is going around in circles.”
It eventually became the much more nightmarish scenario in the final piece, which emerged over a few drafts. Though the monologue is completely different from the list, I can see the connection, particularly in the idea of how suddenly these commercials switch across different terrains. In the monologue, that became:
“I could’ve sworn I passed that waterfall before. But a few seconds ago, I was whipping around a snow-covered mountain, and just before that, everything was rocks.”
This piece might have worked as a list, but I think the character monologue version is a lot more fun to play in.
The piece: This Cleanser Banished My Acne for Good (and for Evil)
The pivot: This was originally a Reductress pitch before becoming a monologue until it finally became a parody of a product review.
The backstory:
This humor piece started as a pitch for Reductress back in 2021. This is what I pitched (when you pitch Reductress, you add the headline and a brief description):
This Cleanser Banished My Acne And Now It Lives On The Outskirts Of Town Plotting Its Revenge
It was worth it, I think? “Thanks to this cleanser, my acne is gone and I fear for my safety.” “I look in the mirror at my flawless complexion and think, ‘Wait, did I just see something dart behind me?’ I’m terrified.”
It wasn’t chosen as a Reductress headline, but I always thought it had legs as a humor piece. So I tried writing it up, but the first iteration didn’t quite land.
The original inspiration for the headline is that I noticed a lot of acne cleansers or beauty products will use the word “Banish” to explain their effects, which always felt very extreme to me. But my initial draft didn’t include any supernatural elements, it was just about a group of zits that were going to hunt you down for banishing them.
I wanted the piece to work, but I didn’t know how to fix it. Then, because it was a few months before Halloween, I realized I could try layering in a supernatural element. That ended up working because it gave me more established tropes I could play with, which opened up more joke opportunities. The final edit I made was putting it into a review format, with subheads labeling all the different sections. That gave the piece more logic / narrative flow, and also gave me more ideas for jokes, like adding in the unboxing moment, which I didn’t have in the original draft.
Unboxing
I’m a sucker for good packaging, so I was a little disappointed that the cleanser came in a plain glass bottle wrapped in an agèd scroll. Once unfurled, it simply read, “Use daily until the Earthly realm is ruled by daemons and the rivers run red with blood. Apply liberally.”
A few takeaways
1) Keep a list of all your ideas / drafts. Months or even years later, you may go back to something that wasn’t quite working the first time, and having that time/distance from it will help you figure out the way forward.
2) Don’t be afraid to try out a new format. Turn a list into a monologue, or a monologue into a list. Would your piece work with a format, like as a product review, a field guide, or a corporate memo? Or alternatively, instead of doing a format, is there a character underpinning everything that just needs to let loose in a monologue? Play around until you find the right match for your idea.
3) If writing a piece feels like pulling teeth, stop and investigate why. I think I’ve gotten better about this now that I’m more experienced. But if a piece is feeling challenging to write and it’s just not flowing, or if something isn’t quite clicking with the comedy yet, that may be a signal that you need to change something up. Maybe the format isn’t quite right for the idea. Or maybe you haven’t clarified your point of view. Or you haven’t identified the “game” (the repeatable pattern that all your jokes will take) yet.
About me
I’m a humor writer, author, and writing coach based in New York City. My work has been published in McSweeney’s, The New Yorker, The New York Times, Reductress, and more. I’m also a co-author of the humor book Jokes to Offend Men, which was named the #2 Comedy Book of 2022 by Vulture and called “highbrow brilliant” in New York Magazine’s Approval Matrix. Since 2022, I’ve been working one-on-one with writers to help sharpen their humor pieces, navigate the submission process, and develop repeatable systems for writing, editing, and generating new ideas.
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