About a month ago, I was in the process of organizing old ideas when it occurred to me that I often work on pieces for way too long, and occasionally abandon drafts way too quickly. As a result, I have a big archive of either finished pieces that I feel aren’t really working, or headlines with little bits and bops.
It’s hard not to feel self-conscious when I don’t write things in a “normal” amount of time (whatever that even means). But some of my favorite pieces are the ones that took me forever to crack. My Modern Love piece started as an essay from the point of view of Peter Piper’s girlfriend that I tried so hard to make work, until I realized the main joke is in the headline (and in the wonderful illustrations by Ali Solomon!). My Subaru piece started as a list around recurring themes in car commercials, before I realized it could really come to life as a monologue.
So, in an attempt to give myself a little inspiration and motivation for tackling these tricky premises, I put out a form in this newsletter asking other writers if they had pieces that took a long time to crack. And they delivered! I’m very grateful to everyone for sharing their process and their pieces. Let’s dive in!
From first having the idea to writing the final draft, how long did this piece take to write?
7 months.
Do you remember the "aha!" moment where you realized how to crack it?
It was originally a monologue, but I had it organized into a big list of outrageous bits. I also had a list of real names from the Sousa band. When I started scanning through the names and bits for more jokes, I realized the bits sounded so funny on their own. And since the bits by themselves sort of read like an oral history, I went with that format.
How does this timeline compare to how long it typically takes you to write a humor piece? Is this longer lead time fairly typical for you, or is this an outlier in your process?
Definitely an outlier. It usually takes about 1-3 weeks from start to finish depending on feedback I get from writing friends/groups.
Is there anything else you want to share about this piece or the process of writing it?
I first got the idea while watching The Dirt. I immediately thought, what if this was a marching band telling these stories?
Do you have any advice for writers about either sticking with a difficult piece, or about humor writing in general?
My advice for sticking with a difficult piece or humor writing in general is to simply keep churning out material. When I have a difficult piece, I just put it in a “not working” folder. Every so often I’ll go through it and something might get resurrected, or it’ll even inspire a new piece altogether.
From first having the idea to writing the final draft, how long did this piece take to write?
It took about a year and a half.
Do you remember the "aha!" moment where you realized how to crack it?
Yes! I originally had written this as a series of responses a teacher might make to a child who is making comments about their hair, skin, relationships -- like all aspects of the teacher's personal life and appearance. The original title was, "Ways that I, a kindergarten teacher, respond to students' questions about my body and relationship status." I wanted to write about the experience of kids making innocent comments that sort of touch on teacher insecurities. I tried to get it into a good spot the best I could and submitted it, and it got rejected. I think the jokes were off, and not quite hitting the funny bone correctly, and it seemed more negative towards kids than I wanted. So I set it aside for a year and a few months.
Then I returned to it because I felt like the general idea had potential and I thought people might relate to it. So I read the piece again and realized that I could try to focus on the most interesting part of it -- when kids ask if you're married -- and expand on that. In doing so, I decided to make it a monologue where the teacher is just responding to that question rather than a series of shorter responses to different comments kids might make. Once I honed in on that singular focus, the piece came together more quickly. Then I had to tweak it further by changing up examples or details within the piece, but it felt easier to revise at this point because I felt as though I had hit on a funny, clear way to get at the idea/the "humor math" had lined up.
How does this timeline compare to how long it typically takes you to write a humor piece? Is this longer lead time fairly typical for you, or is this an outlier in your process?
I usually might take anywhere from a month to a few months to work on something. 1-2 years is more rare.
Is there anything else you want to share about this piece or the process of writing it?
I think it can be helpful to let a piece sit for a while if you're not sure about it. Sometimes returning to it with fresh eyes can help me see new ways for revising it that didn't occur to me when I was writing the first draft.
Do you have any advice for writers about either sticking with a difficult piece, or about humor writing in general?
I think that can be a helpful way to rethink or revise a piece -- look at the part that feels funniest or seems to be working the best. Can you work from there or somehow make that what the whole piece is ...? That technique helped me with another piece I wrote once, too.
From first having the idea to writing the final draft, how long did this piece take to write?
Just under a year.
Do you remember the "aha!" moment where you realized how to crack it?
It was sort of cyclical - the germ of the idea came from thinking about everything we've discovered we got wrong about dinosaurs and what we still don't really know, which made me think of what other species might think of humans in the same context. I played with several formats - buzzfeed style listicles, academic papers, educational sites - before thinking about skeletons in museums, which was really where I started.
How does this timeline compare to how long it typically takes you to write a humor piece? Is this longer lead time fairly typical for you, or is this an outlier in your process?
Definitely longer. I typically work on a piece for about a month, maybe two for a stickier piece, though this one isn't the only outlier.
Is there anything else you want to share about this piece or the process of writing it?
It was hard to translate the idea I had in my head, but the result is one of my favorite, if not most widely read pieces I've written.
Do you have any advice for writers about either sticking with a difficult piece, or about humor writing in general?
Try different formats, and if it doesn't work, try a different one and keep coming back to whatever made you interested in the idea in the first place.
From first having the idea to writing the final draft, how long did this piece take to write?
Almost a year!
Do you remember the "aha!" moment where you realized how to crack it?
I'd never seen a Playbill Bios humor piece before and I was the self-appointed queen of finding discount/lottery theater tickets. I always love reading the Playbills (the image in the piece is my collection from living in New York). The first Google Doc draft in 2018 was titled "Playbill Bios--Just For Fun." I was literally just writing it to amuse myself and thought it might be too niche. I think this piece took so long because I revered (and still revere) Broadway and Playbills and I felt so invested in all of the little details. I guess there wasn't so much of an "aha!" moment as a steady return to the piece to add little details. Eventually, I thought that there was a chance it might amuse others, too.
How does this timeline compare to how long it typically takes you to write a humor piece? Is this longer lead time fairly typical for you, or is this an outlier in your process?
I can definitely revise forever if there isn't a deadline. During the summer of 2019, as I was about to begin graduate school, I had decided to take a yearlong break from humor writing so I could focus on school. So submitting before the start of school became my self-imposed deadline. And that was super helpful! (Did I actually take a yearlong break from humor writing? Nope. I lasted one week.)
Is there anything else you want to share about this piece or the process of writing it?
I kept coming back to this piece because the "research" part was so enjoyable. It was a great excuse to pore through my Playbills. I felt invested in the template and so I wanted to stick with it, even if I never submitted it anywhere--but I'm glad I did! The very nice team at "A Newsletter of Humorous Writing" even included it in their newsletter, which was the cherry on top of a fun--if long--process!
Do you have any advice for writers about either sticking with a difficult piece, or about humor writing in general?
I love co-writing for many reasons, one of which is that there is some level of accountability. When I write solo and there isn't a topical/seasonal hook, I feel like I'm wandering a bit aimlessly through my full-to-bursting Google Drive. Self-imposed deadlines help, as do feedback buddies who will sometimes say, "Whatever happened to that piece?". So my advice is to find people who will ask, "Whatever happened to that piece?", set a personal deadline, or co-write! :)
That’s it! This was fun. Let me know if you enjoyed this special edition and I might do more on different topics in the future.
What’s new:
Friend of the newsletter Claire Tadokoro has a new piece out in Weekly Humorist that cracked me up: “An Influencer Reviews the Cardiologist”
I’m late sending out my newsletter this week. I had a migraine on Wednesday, and on Thursday I had to catch up on everything I didn’t do on Wednesday. So all I can say is: TGIF, and hope everyone has a nice weekend :)
About me
I’m a comedy writer and freelance copywriter living in Brooklyn. My humor writing has been published by The New Yorker, The New York Times, McSweeney’s, Reductress, and more. I’m the co-author of Jokes to Offend Men, which was named the #2 Comedy Book of 2022 by Vulture. I’m available for new writing projects, writing coaching, and nerding out about comedy, so please reach out and say hi!