
Check out my first post here to read more about the namesake of this newsletter and make a copy of the input/output tracking sheet if you so desire.
I’m still on leave!
Popping in with top of mind musings in the weeks after turning 40.
Referral sheet: Check it out here. You can find contact info for humor, satire, and fiction editing; gift book consults; class suggestions, and more while I’m still on leave.
40 for 40
27 felt like my true age until about 33, then 31 was correct until 37, but I feel well and truly 40 right now.
The most random part of my resume: at age 11, I became the first female alter server in the state of Rhode Island. This coincided exactly with me realizing the Catholic Church was bullshit. I spent most of my sacred time snooping through the sacristy and nodding off while serving 7am mass. The priests all hated me and baby it was mutual!!!
Turns out I was drawn to questioning hypocrisy before I ever knew what satire was.
I broke a girl’s wrist and tore off my entire thumbnail in a freak acrylic nail/swimming accident my senior year of high school. Did you know your nail bed has a big, beating vein in it? My swim coach vomited! My thumbnail took a year to grow back and has never been right. The girl whose wrist I broke couldn’t swim in college because of it, but she’s a neurosurgeon now so things worked out.
Pizza is my baseline food. No matter how sick, whether with pregnancy, food poisoning, dysentery (had it twice, don’t recommend), pizza returns me to stasis.
If you're in a slump, go for genre. Read a wild thriller that makes no sense; mainline romantic comedies; watch a string of disaster movies. I was in a depression spiral two years ago and watched The Day After Tomorrow--Greenland--2012--The Perfect Storm--The Poseidon Adventure (the original, grow up)--Dante's Peak--Volcano all in a week's time. Did it cure my depression? No, I needed to up my medication (double it, in fact). But it did put things in perspective—I will never take a cruise.
THE STAND by Stephen King begins in July and thus, is a beach read.
My natural hair color, trying to get back to this! (I also reference this photo on the rare occasions the word “bangs” crosses my mind):
You can be good at something and still have so much more to learn. Being edited by Elissa as we work on our comedy craft book together (INSIDE JOKES, out January 2026!) has revealed my penchant to write in passive voice, use the same five verbs repeatedly, and default to jokes about dog breeds when I’m being lazy. Being edited by someone smart is a gift if you’re willing to accept it.
Once you start doing physical therapy, you need to keep doing those exercises FOR THE REST OF YOUR LIFE to function. Make sure you learn how to do those hip flexor and lower ab exercises correctly the first time.
Special trips: going to the swimming Olympic Trials in Indianapolis with my mom for 8 days in 2000 and watching prelims and finals each day while going to the iMax theater to see Michael Jordan to the Max in between sessions. 10/10 perfect.
An ideal day in Turkey with my husband on our honeymoon. Our friend joined us from Ankara and we explored Istanbul together all day on foot, just the three of us on our honeymoon :)
Spending a week in Jordan in 2019 training incredibly funny writers and comedians who went on to found the wildly successful Amman Comedy Club.
Since I stopped wearing Umbros with free oversized t-shirts my grandfather got me at the casino gift shop at age 14, I’ve never had a defined personal style…until now. Maternity jumpsuits changed my life, and now, post-partum, I have embraced the jumpsuit as my entire personality. This garment from Athleta is magical—made of light tech material, doesn’t show sweat, DOESN’T PICK UP DOG HAIR, and manages to give a waist to me, a person whose body type has been euphemistically described by women’s magazines over the years as “boyish,” “athletic” “straight” and now I think they’re calling it “rectangle” (very sexy). Read the reviews to determine your perfect size, people go hard and write novels for this thing. It goes on sale every few weeks, don’t pay full price!
My mantra for the past few years when I feel frustrated or panicked or trapped: “Just because it’s hard now doesn’t mean it will be hard forever.”
Medication is not for everyone, but I wish I had started taking anti-depressants earlier than the 8th time they were prescribed to me. It was 18 years from the first prescription to the 8th.
No coping mechanism lasts forever. Alcohol is done for me.
If the spirit moves you, just start typing. Don't overthink, don't say "I'll do it when I have more time," write the messy draft. Almost always, you'll get into flow state and hammer out something in its entirety. When McSweeney's sends out writer interviews about their most-read pieces, well over half the time the writer let the piece come out in its entirety when the premise hit them. My most-read issue of this very newsletter exploded out of me a few days after the Oscars in one go. This is one of the best parts of being a writer—why deny yourself?
Don’t write directly in the Content Management System…unless you want to feel truly alive.
A selection of photos saved in a folder called “Pics” on my desktop that I haven’t opened in five years:
Strangest reading experience: leaving the Commodore in Williamsburg the day before Thanksgiving in 2016 to finish reading A LITTLE LIFE because I HAD to finish Jude’s story. Read the final page and immediately took the book out of my house because I never wanted to see it again. Can't say I regret reading it, but can’t recommend the experience, either.
Best reading experience: STATION ELEVEN rewired my brain. The sections on the miracle of airplanes are so beautiful my flight phobia decreased by 80% simply from reading them. My favorite novel of the past decade, to the point I’m afraid to watch the TV series even though I’ve heard that’s outstanding as well. I created an entire college course called “Fight the Future: Dystopia and Post-Apocalyptic Stories” so I could teach this book the year it was published.
Best theater-going experience: for that same college course, I took the students to see a site-specific staging of “Mr. Burns: A Post-Apocalyptic Play” at the Portland Playhouse. Act 1 was set outside around a campfire. Act 2, in the basement of the theater (which itself was a converted church). Act 3, in front of the alter of the church itself. I was absolutely euphoric by the end of this experience. I want to see more theater this decade.
This quote card I saved at some point from a very random website feels very true to me:
This one does not—I fully believe a grudge can be more powerful than those Panera Lemonades that kills people; enough hate in your heart can power a small country:
Cultivate the version of “hello” that suits your personality. In the last five years I’ve landed on, “how’s it going?” as mine. Much better than “hey” or “hi.” More casual, can be be paired with a chin tilt, feels right.
Favorite profanity-free insults: “Get a job” (even funnier if you know for a fact the person has a job, you’re saying they have bum vibes); the classic, “takes one to know one,” especially useful for gendered insults since it will short circuit the person’s brain; and my current fav, “oh yeah?” which implies you’re barely even listening or registering what they’re saying.
Another photo from that Pics folder:
I love writing, but no form of work has even brought me the joy that teaching has. I know I said I was taking off teaching until next year, but I’ve missed it so much I listed a class for November (Write Like an Athlete) and December (Comedy Writing for Non-Comedians).
My teaching career/training has been non-traditional, to say the least. Student taught at middle school in Baltimore, then taught 450 students a week at a public high school in Indonesia. Taught screenwriting to undergraduates at Northwestern; sketch, screenwriting, radio writing, and satire writing to thousands of students online through Second City; wrote classes on scripting, modern comedy and satire, and dystopian novels for an arts college in Portland, OR; now work exclusively with adult learners all over the world. I write all my own classes and always have. Syllabus development is one of the most intellectually engaging activities I do.
I am never more in flow state than when I’m running a class. I never feel more connected. I’m never more tired/overstimulated/content as in the hours following. Seeing a former student get that big publication or deal or job is a form of pride I hope everyone gets to experience at some point.
It’s OK if hobbies burn fast and bright. This time a year ago, I was about to take a trip to spend two weeks exploring fragrances in Italy to inform the book proposal I was writing on the art of smelling good. I returned from that trip pregnant and within a month, every single fragrance I own made me violently nauseous. Post-partum? They still do. The book proposal is on indefinite hold. But wow, if I didn’t have the time of my gd life visiting centuries-old bespoke perfume stores in Florence. Sometime I’ll smell those scents again without gagging.
I want to delete my Facebook profile for good (haven’t touched it in 6 years), but first I need to pull off the only photos that exist of my life between 2005-2010, like these three from my year working in Indonesia:
yes that’s me, visiting Borobudor, the largest Buddhist temple in the world, classily dressed in my sister’s little league shirt. My senior year of college I went to Miami for spring break to live life to the fullest. I got a horrific sunburn on the beach. I saw Little Jon, he of Georgia roll call at the DNC,fame, drink from his crunk cup in a diner at 4am. I had to return to school early when I got a call from my university that the Baltimore police were trying to frame me for the hit and run of a police officer.
I beat the charges!!!! (turns out the cops were just driving around blaming the owners of random cars that were blue. When I took my 1999 Dodge Neon into the station, it was immediately revealed to be a foot too short to be involved).
When I was teaching English in Indonesia right after college, I let the kids pick their own “American” names, like we do here Spanish or French classes (yes, I would not do this now, I was 22 at the time and operating off 6 weeks of training and my own language learning experience). I made the rookie mistake of leaving the room briefly for one class while they picked. 44 of the 45 students chose the name LeBron and one chose Kobe Bryant. Clearly, they had coordinated to mock me. I knew enough to not to back down—I numbered them LeBron 1-44 and made them wear name tags all year. It slowly became a shared bit—we played basketball-themed language games and practiced free throws on the school court in the mornings. They became my very favorite class and I still get messages to this day from "LeBron 17" or "LeBron 3." The other teachers thought this was some sort of weird American educational strategy—but it was just me loving my LeBrons. And that one Kobe? I made her my class assistant.
I’m a slow learner, but once I learn something, it’s in there. Once I stopped being embarrassed by the things I didn’t know, my intellectual life truly started.
The perfect is the enemy of the good, so I’m going to send this out now, typos and run-ons and punctuation errors and all.
Any 40 for 40’s on your mind to share with me?
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ABOUT ME: My name is Caitlin Kunkel and I’m a comedy writer, long-time teacher, and creator of The Second City’s Online Satire Writing Program. I currently teach classes and consult on gift book proposals, modern adaptation, satire, and comedic literature. I co-founded The Belladonna Comedy and the Satire and Humor Festival, and I co-wrote the satirical gift book New Erotica for Feminists: Satirical Fantasies of Love, Lust, and Equal Pay, named one of the Top 10 Comedy Books of 2018 by Vulture.
I’m Caitlin’s dad, Larry. While Caitlin was in Indonesia, Monica and I spent Christmas with Caitlin in Bali. On a visit to a “sacred” monkey sanctuary in Ubud, a monkey stole Monica’s water cup, drank the water and threw the cup at Monica. That monkey then had the temerity to mock my wife. I then tried to kill that sacred monkey bastard with my briefcase. I’m very disappointed with Caitlin for not sharing my courage and outrage. I forgive you!
I read both Station Eleven and Mr. Burns in a college class on dystopias. It wasn't your class but I shouldn't be surprised someone else would be inspired by the same novel. They were both really good and fit well together in a curriculum.