What I’ve Learned From My Writing and Comedy Mentors and Teachers
Don't underestimate the power of a good teacher or mentor...
I’ve had several writing and comedy mentors, teachers, and coaches over the years, and when you put them all together I’ve learned a hundred supremely valuable lessons from the lot of them.
The right mentors and coaches can quickly pinpoint your bad habits. They can help you overcome middling work much faster than you would or could on your own. And they have a highly positive effect on your mindset and standards.
Spending time around smart, funny peers is great. You should do that. But when you spend time around the right mentors and teachers, they elevate your thinking in a different way.
Today’s post is a shout out to some of those I’ve learned from.
Trying to recite every last lesson from every teacher would be ridiculous. First of all it would be impossible: we learn a lot from our teachers and mentors that we internalize and can’t articulate. But also, it’s just simpler for me to focus on a few highlights rather than recount every last lesson. So here goes.
One of my first writing coaches who gave me feedback on my humor drafts, Allison is more of a literary writer (essay, fiction, etc.) than a “comedy person.” But I realized right away she had great humor writing instincts. And I worked with her partly because I wanted to become a better writer generally, not just a better funny writer.
“Who is speaking here and why?”
This is a question Allison wrote in the inline comments on some (probably pretty bad) draft of mine. The draft itself was some forgettable piece that I don’t think I ever published, but, man, that question stuck with me. I had drafted some kind of weird monologue where the narrator had a mysterious, unclear identity, and the reader couldn’t really be sure what was going on or why.
When comedy writing is confusing and the audience doesn’t know what’s going on, the comedy almost never works.
But this lesson also marked a slight shift in my writing practice: I started thinking about the reader, just a little bit more. What can I expect the reader to understand at this point? Are they in on the joke? How can I be clearer so we can be on the same page?
I liked Allison’s question so much I referenced it in my 21 humor writing mistakes piece:
Bill is a novelist and rare book dealer, and I was lucky to get some coaching from him years ago when he did that. His debut novel Fever Chart is one of my very favorites. It’s simultaneously hyper-literate, hilarious, bizarre, and engrossing. High recommendation!
I learned a lot from Bill, but one lesson that stood out is how important it is to read everything and be a perpetual, voracious student of the written word. Bill legitimately and seriously loves books and reading, and before we met for coffee the first time, I assumed that because of his intelligence and hyper-literate style, he would be some intimidating literary figure with impossibly high standards, speaking in riddles and enigmas.
Actually, I didn’t entirely assume that since it was already clear from his written comments that he was a thoughtful, helpful, and and sweet teacher. But I was surprised that Bill recommended I read and learn from every type of book that I possibly could. He told me to read funny books but to also learn from harlequin romances and Stephen King and old books and new books and pop sci-fi and literary writers (like his favorite author, Nadine Gordimer.)
Every time Bill and I met to talk about books and writing, I’d always walk away wanting to read more. A good mentor can rub off on you and inspire your mind.
I took Caitlin Kunkel’s Second City writing course—“Writing Satire for The Internet” several years ago. She didn’t just teach the course, she designed it and wrote the curriculum, and several other teachers went on to teach her satire course with that curriculum, after Caitlin moved on to other projects.
Sure, there were lessons aplenty about satire and humor writing per se, but one of the big takeaways was this: be a professional.
I think a lot of newer comedy writers are challenged by this one.
Just because you’re writing funny and absurd stuff doesn’t mean you should wing it and have the writing and professional habits of a clown-slob.
Those of us who went through all 3 levels of Caitlin’s course had to create a personal-professional website for our humor writing. At the time, I was a couple of years into my journey, and I either didn’t have a website yet, or I’d just started a super rudimentary one (memory hazy—it was a while ago), mainly out of laziness.
As a class exercise, we drafted a short writing bio that would go up on our new website.
One of the guys in our class tried to put some self-deprecating joke on his site copy about how his writing was underdeveloped or lame and generic or something, and Caitlin immediately shot him down.
She was very happy with us making jokes in our bios (and she recommended that humor writing bios should have at least one joke). But she strictly forbade that kind of public, limiting self-criticism. It’s weak sauce and not professional. Put your best foot forward. Show your work and be proud!
Caitlin’s style of structured, professional feedback impressed me in that course, and it marked the start of my journey from using mainly local writing groups in Austin to using online writing sprint groups with peers all over the country (and overseas).
(Not that the local groups were bad whatsoever, and I do miss them. Post-COVID it was just not a thing for me any more.)
Caitlin’s class convinced me that the best writing groups would:
(a) have peers with similar goals and ambitions—peers who were really good at giving feedback, and
(b) would give both hyper-specific inline feedback and bigger-picture holistic feedback.
In the Substack universe, Caitlin runs an interesting one called Input/Output. Check it out!
Aside from being a sharp, very funny writer—love his piece on the relationship between showering and writing—Luke is a wonderful writing teacher and coach. He teaches a variety of humor writing workshops.
Here’s something Luke told me once that stuck with me, after I bugged him to give me some bigger picture notes about my work.
I’m paraphrasing, and Luke probably said it more eloquently:
“one of the biggest difference between beginner-to-intermediate humor writers and more advanced writers is that the more advanced ones are willing to make bigger structural changes to their drafts. They’re willing to scrap and overhaul in a more radical way.”
This stuck with me, and man oh man, have I found it to be completely true.
Plenty of drafts have a promising concept, but the first or second attempt has deep problems than cannot be overcome just with cosmetic changes or a few joke rewrites. Sometimes the piece needs a completely different voice, format, narrative, or overall structure. The true professionals are more willing to torch the first attempt in service of The Funny Concept.
Luke also runs, with James Folta, A Newsletter of Humorous Writing, which is an important resource in the humor writing community.
