Great Questions About Humor Writing, Part II: Mindset
Humor writing involves two battles: The first battle is getting the right words on the page and shaping them into something funny.
The second battle is dealing with the psychological blocks that stop you from winning the first battle.
If you don’t like war metaphors, I feel you, my dude, and I invite you to replace “battle” with “spiritual trial” or some other hippie, Zen thing.
The important thing is that today we’re talking about the mental game of humor writing: feelings of inadequacy, burnout, a “lack of joke ideas,” or just plain bewilderment with the process of writing funny stuff.
In the previous installment of this two-parter—Great Questions About Humor Writing, Part I—we looked at questions about the craft of a humor piece.
So, in Part II, let’s look at some mindset and self-growth questions about humor writing.
A note about where these questions came from: Recently, I co-created a contest for comedy writers called The Better Writer, Better You, Doin’ It With Mike Sacks Supreme Comedy Writing Contest. This contest was for helping comedy writers hone their craft.
During the contest, I received dozens of questions on humor writing. The questions were so good that I knew they were worth answering in a series of two pieces.
Okay, on to the psychological questions!
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Do I deserve to be funny?
"How do you retain the feeling that you deserve to be funny?” - A.K.
I remind myself of three things:
First, I know what's funny to me. Humor writing is just pointing this out in a clear, unique way. So rather than asking whether “I'm funny," which is a pretty heavy question, I just focus on things that I observe to be funny. Thus, I externalize and shift the existential question of whether I’m funny into the lighter, easier question of what's funny to me right now. Then I realize how enjoyable it would be to write it down.
Second, I know that humor writing, and all comedy, is a skill. Every human skill is improved slowly, by deliberate practice. Every funny writer worked their ass off to perform well on the page. So I focus on this: "What can I do this week, this month, this year to get 10% better at my craft?" That's a helpful and focused question. From there, I can remind myself that every funny writer in history had to give themselves permission to write in order to become the funniest writer they could be.
Third, I remind myself that I write humor because I love it, and loving it is a fine reason to show up and write every day. A carpenter won’t much be helped by asking, “how do I give myself permission to build a birdhouse?” Likewise, a surfer won’t be much helped by wondering, “How do I give myself permission to ride waves?” The point is that enjoyment of the craft justifies its existence. You don’t have to be the savior of the sparrow to build birdhouses, and you don’t have to be Laird Hamilton to surf. Jettison your pretensions of greatness, and write some jokes, gosh dang it.
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How do I make time for writing?
"When you have writer's block, what do you watch, read, or do to get new ideas? How did you make time to do your comedy writing with a day job before you started making money?” - K.B.
I believe this dictum about writer's block: “What the non-writer calls 'writer's block' is just what writers call ‘writing’.”
(I wish I could attribute this quotation because it’s a great one, but I don’t know who said it.)
I think humor writing is always a challenge, and it's just a matter of showing up like a pro and putting words on the page while honoring your instincts of what’s funny to you, however imperfectly at first.
One of the advantages of writing funny articles is that it’s not hard to do in short bursts. Whether you have a day job or not, I recommend scheduling and time-blocking your writing. Find anywhere from 30-90 minutes a day, and schedule it in your calendar or planner or whatever, then do it no matter what.
Let’s say you schedule 45 minutes of writing each day during the week. You could do it before work, during a lunch break, or right after dinner, or whatever. You can always find 45 minutes to write a few jokes, or a funny headline, or to punch up a recent draft, right? I bet you can.
But regardless, schedule your writing in advance, like a Zoom meeting with the president of a Scandinavian country, or like a guitar lesson that you paid for. That way, you’re sure to show up. (For more resources on humor writing, here’s my Ultimate Humor Writing Cheat Sheet.)
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Should I self-publish?
"I often feel discouraged talking about or sharing my humor writing as I don’t yet have any of the notable publication credits I’d like to have to back it up. While not my original goal, is there still any merit to self-publishing through a site of my own if I’m trying to quote “establish myself” or do I just need to keep submitting and hold out for an accepted piece?” - B.G.
Yes, there is great value to self-publishing, especially early on, but also at any stage.
When I started writing humor, I self-published the first 100 pieces I wrote. They were almost all pretty bad and not funny. Maybe five of them were good. I focused on just writing one or two humor pieces per week. In the beginning, just write and develop the habit. Don’t worry about anything else. Self-publishing works great for greasing the groove and building the practice of writing funny stuff every day.
As far as making it into publications, your craft will improve over time as long as you stick with it, and as long as you have an intelligent, focused plan for improving. Every three months, take a step back and assess your progress. Then change your game plan if needed.
I would also recommend a "mixed strategy" of self-publishing and focusing on output, but also occasionally sending your best drafts to humor publications. Build momentum! And keep going.
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How do I find my voice?
"How did you find your voice as a humor writer?” - A.D.
I think your voice arrives as a natural result of just writing humor consistently. It emerges over time. However, I believe a writer's humor writing voice develops more naturally when:
1. You focus on writing what truly delights you and makes you laugh.
2. You read well. And you stop when something is truly funny and ask, "Why is this funny? Why does this work?" Stay a lifelong student. And keep honing your taste.
3. You dedicate yourself to the craft itself, you have a plan to keep growing, and you commit to showing up like a pro.
If you do all this, your funny voice will find you.
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How do I find a humor writing group?
"How the heck do I find a decent writer's group? It's been by far the hardest thing I've found about the satire writing process.” - J.M.
I agree that finding a good group is a challenge, and I recommend these three things:
1. Take online writing classes, and reach out to the writers in the class that you vibe with. Tell them you want to start a small group. You have my permission to reach out to your favorite people in the class, not everyone.
2. Participate in online comedy writing forums. Post and reach out to people.
3. Email specific internet humor writers who you like. Stick with writers who are somewhat near to you in their experience. Strike up a conversation. If they respond, see if they're open to trading feedback or starting a small group. Some people are likely to say ‘yes.’ You might be wondering, “Am I really allowed to just email writers I don’t even know?” The answer is ‘yes.’
Finding the right writing group is work, but it's worth it. Go for it.
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How do I share with loved ones?
"How are you supposed to answer your loved ones when they ask how comedy writing is going?” - S.M.
Assuming this loved one is someone who I have a healthy relationship with and they are a generally reasonable person, I would just answer honestly. If I'm excited about a certain comedy project, I'd talk about that project. If I'm frustrated about something in my writing life, I'd give them the gist of it without over-indulging or falling into complaint mode. I would try to be real and honest with them.
If those caveats do not apply, and the relationship is not fully healthy, I would give a more brief, cursory answer and then shift the conversation. In this case, I would understand that this loved one’s reaction may be inauthentic and based on whatever's going on with them, and I'd behave accordingly.
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How should I get organized?
"How do *you* organize yourself and your ideas?” - A.G.
For planning purposes, I create quarterly writing goals, a weekly plan, and I plan each day and make sure my writing fits in. I try to approach my humor writing like I'm the CEO of my own startup called Write Funny Shit, Inc.
For organizing my humor writing ideas per so, I have experimentally found the following system of folders:
Writing — Working: This is my folder for pieces I am actively writing.
Writing — Hibernating: This is where I keep all the pieces that I think have some promise but I am not actively working on them.
Writing — Graveyard: These are all of my unfinished pieces, or failed drafts, that I don’t want to publish or work on anymore.
Writing — Ready: My finished but unpublished pieces. I keep them in one spot so I’ll remember to get them out there in the world.
Writing — Published: My published stuff, for reference. I can glance here when I’m feeling a little discouraged and pump myself up: “See, look! Past Me wasn’t a failure!”
For active projects, I track the status in a To-Do app (Things 3 on Mac/iPhone).
For raw ideas, I write joke and headline ideas in a Mac notes file, and I try to do this daily. Nothin' fancy!
You are welcome to copy my system, and if so, you owe me $30.
You can find more details on the system in this Writing Cooperative piece, How to Be a More Prolific Humor Writer.
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How do I recover from burnout?
"When you get burned out from writing comedy, what type of breaks/rest helps you get back in the groove?” - L.C.
For me, five things:
Reading good books and enjoying the hell out of them.
Investing in friendships and relationships.
Traveling a little, if possible.
Taking care of my health and my sleep.
Getting outside my head by spending time on one interesting hobby that has nothing to do with writing. For me, that’s dance.
Those are my top five, and if I do a few or all of them, I'm aching to write again soon enough.
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Ready to improve your humor craft? Get The Ultimate Humor Writing Cheat Sheet, my tips and tricks for writing and publishing humor in places like The New Yorker, McSweeney’s, and Slackjaw.