Caitlin Kunkel is a writer, teacher, and speaker whose work has been featured in The New Yorker, McSweeney’s, on public radio, and across the vast internet. She’s the co-founder of the comedy site The Belladonna and the Satire and Humor Festival, created the online satire writing program for The Second City, and teaches workshops across the US and internationally.
Caitlin’s second book, Inside Jokes: A Comedy and Creativity Guide For All Writers, will be published by Grand Central on October 20, 2026, and is available for preorder now!
Below, Caitlin answers 10 questions about INSIDE JOKES, which I think every writer should read:
How did this book come about? Was it sold on proposal?
Yes, the book was sold off a proposal—nonfiction books usually are, and especially resource/craft books. The proposal itself was quite long, I just went back and checked and it was 126 pages now which is NOT NORMAL! I sold my first gift book off a proposal as well and that one was only 41 pages with a lot of white space. But for Inside Jokes we wrote out several long sample chapters, had detailed chapter summaries of the rest, and then we included blurbs from writers and wrote out six distinct sales avenues we would tap into. We knew that a comedy craft book might read a bit niche to traditional publishers so we wanted to take the time to really lay out the vision for the book itself as well as how we would sell it.
The proposal took about two years to get right, with my wonderful agent giving generous notes and feedback during that time. We sold the book to Grand Central in November 2023 and we were done with the manuscript itself in June 2026. (It took…much longer to come together than anticipated.) Five years from start to finish was about a year longer than I wanted, personally, but that’s publishing for you!
You write that comedy writing is “risking being terrible to become good.” In this increasingly polarizing and unforgiving time, how do you, personally, navigate that journey?
I spent my 20’s and 30’s experimenting with comedy in Chicago, Portland, OR, and NY, writing, directing, and producing sketch comedy, performing improv, and co-founding a satire website and a humor and satire festival. In each of those endeavors I made mistakes—I published a piece that needed more editing, or booked a panel that didn’t gel, or I put a sketch into a show that didn’t have a clear point of view. And you know what? It was all good. Yes, there are bad faith people who will try to come after you when a joke or comedic premise fails, but at the end of the day, I work with people who I know are writing and creating in good faith, and I’m doing the same. If my intent is good but I miss the mark due to trying something complicated, then that’s a learning experience rather than a failure. You will never get better without working at the borders of your ability.
So many of our interviewees for Inside Jokes said to get good at comedy, you have to have a thick skin and check your ego at the door. If someone hates a piece I write and sends me a mean DM, it really rolls off my back these days. If I get a rejection, oh well! I know I can write another piece. Not all comedy is for everyone (and if you try to make it for everyone, your work will be bland and boring) so I know my audience and write to them. In the book, we talk about this a lot—you are your first audience, then trusted readers, then potentially an editor, and only then, readers and literal audience members. If you never push the line, you’ll never know how far you can go. The chapter in the book, “Joking About the Impossible” covers this in depth—we call it the graduate school chapter.
What do you wish you’d known when you started your comedy writing career?
I wish I had known to be more discerning about the people I collaborate with. I’ve worked with 90% amazing, dedicated, funny, smart people, but comedy definitely attracts some darker personalities who can really make a project or show or experience a truly bad time. I’ve often been too quick to jump into working relationships with people when I should have taken a step back and gotten to know them on a personal level first. One thing I’ve noticed is that there are people for whom comedy writing is a job (I’m in this camp)—yes, it’s fun! But there are deadlines and professionalism and you have to do it at a high level when you don’t feel like it. Then there’s another camp where people treat comedy like a mystical process that can’t be done on a deadline or in an orderly way, and I do not mesh well with that mindset. So: be more discerning about who you give your time and energy to, younger Caitlin!!
What is your interest in M. Night Shyamalan?
The book’s dedication to M. Night Shyamalan started as—you guessed it—an inside joke between me and my co-author, then it became a real one we kept returning to. At one point I was working on a section for the book on the intersection between comedy and horror (it ended up being cut for space). I rewatched the M. Night movie The Happening which is unintentionally one of the funniest movies I’ve ever seen (spoiler alert for a movie that came out in 2008: the villain is the wind). From there, the inside joke grew and grew until we decided hey, we both unironically love M. Night Shyamalan, why not dedicate a comedy book to him? The beauty of an inside joke is that no one else needs to get it.
Can you humor me and provide one last writing prompt for our audience inspired by INSIDE JOKES? [I know you gave us many in the book!]
Use the comedic tool of contrast and rewrite a scene from your favorite classic/older book in a modern context. Use contemporary, heightened words and phrases like Beowulf using the word “bro” in a recent translation. What would Aesop’s fables in 2026 sound like? How about the story of the Princess and the Pea? Is she sleeping on a foam mattress she got online? What about something like a Judy Blume book—what if Margaret was in the show Euphoria? Have fun!
What is your favorite revision strategy? [I know you gave us many in the book!]
For me, there’s nothing that compares to asking a smart, funny friend for feedback—the second they say, “sure, send it to me!” the scales fall from my eyes and I can see how bad my draft truly is. Then I edit in a sweaty panic until it feels worthy of their time and wisdom. If you collaborate with people you respect who are slightly better than you, you’ll always be pushing yourself to work on their level.
You quote Sarah Cooper ending her memoir with, “…It’s not for me to say what you should take away from this book,” but I admit that’s a question I do always ask guests, so humor me —What do you most hope people take away from this book?
I hope they take away that comedy is a technical form of writing, so the same way you learned a five-paragraph essay in high school, or how to write in a specific cadence and voice at work, you can learn to use comedic tools and write comedy. Yes, some people have natural comedic timing or the ability to pop off with an amazing one-liner, but many of the students I’ve worked with over the years have been engineers, copy writers, teachers, social workers, scientists, journalists, even an undertaker. And they have all been able to learn and implement these tools to create extremely funny work, just as they learned the skills needed for their primary careers. If you want to learn how to write comedically, you can—if you’re willing to put the work in.
On a related note, what do you think comedy writing can offer the world in 2026?
I think it can offer people a form of intellectual play. The world is so grim, the fire hose of the news so unrelenting, that it’s easy to succumb to mental numbness. Comedy writing is about noticing, curiosity, pattern recognition, absurdity, and so much more that lights up the brain and encourages you to look at the world through a different lens. It gives people an outlet to process what is going on around them—for satire, specifically, I say that it’s like looking at the world through a funhouse mirror. I don’t think comedy can change the world, per se, but I do think people using comedy as a tool to engage with reality in a new way can lead to those people changing the world around them.
“I don’t think comedy can change the world, per se, but I do think people using comedy as a tool to engage with reality in a new way can lead to those people changing the world around them.”
CAITLIN KUNKEL
Which release events are you most excited about?
While I can’t wait for my NY release event with my amazing writing group, A Great Week for Women, I’m so excited to return to Chicago, where I began my comedy writing career, to teach a workshop, host a show, and then have office hours for students at The Second City Training Center. I first started teaching sketch comedy in-person at the Training Center in 2011, went on to create the Online Satire Writing Program that still runs eleven years later, and even went to Jordan in the Middle East to train comedians in satire with them.
Second City has shaped my comedy mentality and I can’t wait to engage with the new generation of comedy writers who are working there now.
Interested in being a future featured Tightwires guest? Let me know!