This is the last Challenge post before I wrap all these posts in saran wrap and blast them toward Pluto.

Thanks to everyone who gave me feedback.

I love hearing what the Challenge did for your writing. (Have you thrown your opinion into the mix there?)

A nice big picture comments came from a subscriber, Erik:

Honestly, at the beginning of this challenge I thought I would barely squeak out 3 to 5 ideas.

And the first half of the challenge did feel kind of like that. I started to worry the well would dry up at some point.

But as I kept going, I started picking up momentum. I’ve had a few days where I’ve had more ideas come up than the minimum I set for myself. They weren’t all bangers, but I was able to think them up and type them up and share them with everyone here. Some of them seemed to land better than even I thought they would.

And this is also what I’ve found in my own creative process: the act of relentlessly writing comedy ideas every day does not make the well run dry. On the contrary, it overflows.

If you did the Challenge and would be willing to throw in your $0.02 about how that went, please do that here. Only takes 4 minutes.

Anyway, today I’m recapping my favorite humor headlines (part 2) and favorite sketch comedy premise ideas.

First, PSAs.

Can you still read the Challenge posts? Hell yeah! Find all Challenge posts here.

I’m leaving Challenge posts up as free posts just through this Sunday, Jan 25. After that, they’re for paid subscribers only.

Second, I know of bunch of you subscribed to join this Challenge, or just to loosely follow along.

If that’s you, I invite you to stick around in the coming months and keep working on your comedy writing. Here’s what I focus on at Comedy Bizarre:

Comedy craft: I write posts and deep dives about how to escalate your comedy writing, write stronger jokes, and how to be more surprising and creative.

Growth and self-development for comedy writers: I write about the long game of improving your comedy mind. Think: nerdy self-development, but focused on comedy and without the BS platitudes of the fuzzy, magical thinking podcast world.

Publishing and growing your audience: I write posts about how to publish, get your work out there in the world, and find an audience.

Community: This place is not just my weird outlet, it’s also a community of writers. There will be more challenges in the future. And I have a new writers’ room feature I’ll be launching—for those looking for regular feedback. More on that to come.

If you want an idea of the kind of posts I write, here are three Deep Dive posts that were all popular and pretty representative of these categories.

So, to all new subscribers: hope to see you around in the coming weeks!

Okay, onward to my final favorites of the Challenge…

Best of the Challenge, Pt. 2: humor headlines and sketch comedy

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Well, we did it. The 14 Day Comedy Writing Challenge is doneskies.

Congrats and thanks to everyone who followed along and wrote every day.

I hope you were inspired by the daily writing tips, the comedy brain-building examples, and the writing prompts.

Real quick. If you did the Challenge, help me make the next one better: answer a few questions, please. Takes 4 minutes. I mucho appreciate it.

Also, to all subscribers who are still planning to check out the Challenge posts, and do it self-paced, you can do that.

Find all Challenge posts here.

I’m leaving these Challenge posts up as free posts only through the end of this week. After that, all Challenge posts will be paywalled, for paid subscribers only.

In fact, you might say, “hey, the posts now say ‘paid’ on them.”

That’s because I added paywall breaks at the very bottom of each post, just above the comments section. But the posts themselves still have all of their content visible to free subscribers. (But only through this week.)

Anyway, I added paywall breaks above the comments sections because I wanted to make all the comments invisible from search engines and the general public. I decided it’s a good idea to protect everyone’s idea pitches.

So, if you pitched something in the Writers' Room (comments section), your idea pitch is not visible to search engines or to the public. It’s only visible to paid subscribers from now on.

For the same reason, I’ve decided to make my “Best of the Challenge” selections only visible to paid subscribers.

So, here you go: My favorite comedy writing from the entire 14 day Challenge.

Necessary disclaimer: I call it “Best of the Challenge” but that’s just a headline hook. (Ha ha, gotcha.) Comedy is subjective, so these are just the idea pitches that made me laugh the most, or that I found the most comedically promising.

And, yes, I read every single comment from all 14 days. Thousands and thousands of them. Obviously, there were plenty of other funny pitches, ideas, and jokes that didn’t make my list.

Today, I’m shouting my favorite stand-up jokes, short story pitches, and half of my favorite humor headline pitches, from the comments section.

On Thursday, I’ll shout out my favorite sketch comedy premise ideas, and the other half of my favorite humor headlines.

There’s a lot to learn and celebrate with these ideas, so let’s dig in…

Best of the Challenge, Pt. 1: Stand-up jokes, short story ideas, and humor headlines

Read more

Welp, this is it. The final two days of the The Challenge.

There are no posts on the weekends. Spend all your time writing, instead.

Here’s a comment thread where you can post your final Challenge comedy pitches for Sat 1/17 and Sun 1/18.

Enjoy!

p.s. If you’re doing the Challenge, answer a few questions to help me make the next one even better. (takes 4 min…

Read more

Welcome to day 12 of The 14 Day Comedy Writing Challenge.

Today is the last post of the Challenge.

Starting late? Here’s the Day 1 post explaining everything, including the true meaning of that STRANGE email your uncle sent last week.

Find all Challenge posts here.

Challenge Posts will remain free for one more week, then they’ll be locked for paid subscribers only.

I’ll send a Challenge wrap-up on Monday (edit: on Tuesday, actually!), including the “Best Of The Challenge.” I’ll shout out my favorite headlines, jokes, sketch and story premise ideas that you posted in the Writers’ room, starting next week.

Real quick, I need a little help!

If you’re doing the Challenge, answer a few questions to help me make the next one even better. (takes 4 minutes.)

Now, onto the final post!

Sometime back in the summer of 2016 I was on vacation in Portland, hanging out at this tea shop called Tea Chai Te.

The shop was built partly out of an old train caboose, and they sold dozens of different types of gourmet teas. It was a real charmer of a joint where one can post up with a laptop and feel inspired for a long time.

I was sitting on the back patio, in this peaceful courtyard, drinking my hipster tea and pounding away at the keys, working on some humor piece that I can’t remember. I think some lovely birds were gently circling my head and there was a little fountain and, for some reason, a mini triple-rainbow floated directly over that fountain.

Read more

Welcome to day 11 of The 14 Day Comedy Writing Challenge.

We’re getting close.

Just finding this? Here’s the Day 1 post explaining everything, including why pirates are cooler than ninjas but far less deadly.

Find all Challenge posts here.

Sometimes coming up with comedy ideas feels hard. Sometimes it feels easy. Depends on the day.

Here’s a way to make it easier: Go to premise island. This is a tropical paradise where ideas have sex and multiply.

How does this happen? Well, the ticket is this…

Read more

Welcome to Day 10 of The 14 Day Comedy Writing Challenge.

Just getting started? Here’s the Day 1 post explaining everything, including why a Klein bottle has no inside or outside, unlike a traditional bottle.

Find all Challenge posts here.

One of the reasons we get stuck is because we keep doing the same shit, over and over.

The grooves of habit are deep and powerful.

I hope your 10 days of the Challenge have been mighty inspiring, full of funny ideas.

But in case you get stuck, here’s something to consider.

In comedic writing, we talk about the supreme importance of voice.

Read more

Welcome to Day 9 of The 14 Day Comedy Writing Challenge.

Just getting started? Here’s the Day 1 post explaining everything, including what’s on the other side of an Einstein-Rosen bridge, aka a ‘wormhole.’

Find all Challenge posts here.

In comedy writing, complexity is the enemy.

Most really funny ideas are pretty simple.

And lots of failed jokes or unfunny comedy premise ideas are convoluted.

Trust me. I know this from being King Convoluted.

I have truly reigned on the throne of “Bro, what the hell are you trying to say here?” in the kingdom of “This is six paragraphs too long, bro. You’re killin’ me, bro.”

Read more

Welcome to week 2 of The 14 Day Comedy Writing Challenge.

We’re halfway there, baby.

Just getting started? Here’s the Day 1 post explaining everything, including why cilantro tastes bad to you.

Find all Challenge posts here.

(Subscribers not doing the Challenge: You can toggle off Challenge emails only.

Go to Settings > Manage subscription > Email notifications and toggle off the Challenge section. Easy to turn back on anytime. Regular Comedy Bizarre posts still land in your inbox as usual.)

Let’s say you finish this week’s Challenge. (And I hope you do.)

And let’s say that you put in around 20-30 minutes daily for idea generation, and you average three new writing ideas per day.

Some days are rushed. You spend 10 minutes and get just one idea. Others are bountiful. You have a peaceful forty minutes where you crank out 7 jokes in a row.

Read more

Happy weekend, all.

We’re nearly half-way through the 14 Day Comedy Writing Challenge.

Just getting started? Here’s the Day 1 post explaining everything.

Find all Challenge posts here.

Read more

Welcome to Day 5 of The 14 Day Comedy Writing Challenge.

This is the last week 1 post!

Just getting started? Here’s the Day 1 post explaining all the things.

Find all Challenge posts here.

Today, I have a bit of short advice from an esteemed comedy-writing guest and friend of Comedy Bizarre, humor writer and author Eli Burnstein.

Eli is the author of a banger of a coffee table book for anyone who likes language, “The Dictionary Of Fine Distinctions.”

He’s also written some of my favorite New Yorker Shouts & Murmurs pieces.

Eli has a Substack Newsletter called Oozeletter - .

Getting in the Comedy Mood (by Eli Burnstein)

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Welcome to Day 4 of The 14 Day Comedy Writing Challenge!

For reference:

• Here’s the Day 1 post explaining The Challenge.

• Find all Challenge posts here. (Bookmark that link.)

Today’s tip is about brevity:

“Brevity is the soul of wit.” — Shakespeare, Hamlet

“The secret of being a bore is to tell everything.” — Voltaire

“Often, cutting is the best answer.” — Jack Handey

Read more

Welcome to Day 3 of The 14 Day Comedy Writing Challenge.

Just getting started? Here’s the Day 1 post explaining all the things.

Find all Challenge posts here.

Today, let’s talk about two modes of being creative.

One mode is more open, free, and uninhibited.

The other mode is more critical, self-aware, and perfectionist.

Read more

Welcome to Day 2 of The 14 Day Comedy Writing Challenge!

Just getting started? Here’s the Day 1 post explaining everything, including the meaning of life.

Find all Challenge posts here.

(Quick note for longtime subscribers not doing the Challenge: You can toggle off Challenge emails only. Go to Settings > Manage subscription > Email notifications and toggle off the Challenge section. Easy to turn back on anytime. Regular Comedy Bizarre posts still land in your inbox as usual.)

Alight, let’s crack into it, friends.

Comedy writing has few if any “rules.”

You want to be free and loose and fun with your comedy writing.

Read more

Welcome to the 14 Day Comedy Writing Challenge!

It starts today and runs January 5 - January 18.

This Challenge will get you writing comedy ideas fast.

It will build your comedy writing habit with a simple daily exercise that will transform you into a joke-writing BEAST.

This Challenge is free to join: everything you need to start is in this post.

One free post every weekday: For the duration of the Challenge (Jan 5 - 18) I’ll post every Monday - Friday.

Each post will have a practical comedy writing tip, funny examples to inspire you, and writing prompts to nudge you.

Accountability and feedback: Every post will also have a Comedy Bizarre Writers’ Room—a comment section for feedback and accountability, starting today, for paid subscribers.

If you’re just learning of the Challenge, here’s two of the pre-launch week posts: How to Prepare for The Challenge, FAQs About The Challenge.

You can always find All Challenge Posts here.

There are four Challenge tracks. Pick any one:

• (1) Humor writing: Write at least one comedic headline per day for 14 days.

• (2) Sketch comedy: Write at least one comedic sketch premise idea daily.

• (3) Stand-up: Write at least one stand-up joke or social media one-liner per day.

• (4) Fiction writing: Write one comedic short story premise daily.

Why one idea per day?

• Simplicity and low friction: You can do it in fifteen minutes a day. It’s hard to make excuses.

• Consistency: By doing the same, simple exercise each day, you get consistent daily output.

• Momentum: It builds a habit. Psychology nerds and brain scientists can argue when a “habit really forms” but 14 days nonstop is a great start.

• Volume: When you write daily, the wins stack up: Quantity Wins.

• Premise = half the battle. A clear, funny premise is half the battle in making great comedy. The more premise ideas you have, the more success you’ll have.

• Idea feedback = smart vetting. Simple premise or joke ideas are how you vet your ideas with feedback. Make sure you’re on the right track before you commit to writing an entire piece, story, sketch, or routine. It’s the smart way to do comedy.

One idea per day is the minimum. You can write more than that.

Ready to do this? Here are the rules for each of the four challenge tracks…

Read more

The 14 Day Comedy Writing Challenge starts Monday.

It runs Jan 5 - Jan 18.

This Challenge will help you build a comedy writing habit in 15 minutes daily. By the end of the Challenge, you’ll be on fire!

The details are here in Monday’s post.

Find all Challenge posts here.

Today I’m answering some questions about The Challenge.

Let’s go!

“How do I join The Challenge?”
Just subscribe to Comedy Bizarre. If you’re already subscribed—i.e. you got this post by email—you’re all set. I’ll send you Challenge posts starting Monday. If you’re not subscribed, sign up here:

“What exactly am I writing each day?”
One of the following, depending on the track you choose:

• Humor track: Daily humor piece headlines (humor premise ideas)

• Sketch track: Sketch comedy premise ideas

• Stand-up track: Stand-up or one-liner jokes

• Fiction / Short story track: Comedic short story premise ideas

Just make sure you’ve chosen your Challenge track. More in Thursday’s post.

I’ll give you all the details about each track when the Challenge starts on Monday.

“Do I have to pick just one track or can I switch it up each day, mix and match?”
Pick one track and stick with it. Consistency leads to more momentum and compounding results.

If you really want to experiment with different comedic styles, try two different tracks, one per week. I recommend that whatever schedule you choose, settle it in advance and commit to it. Don’t hop around willy-nilly, from day to day.

“How much time should I budget for Challenge writing per day?”
Budget 15 - 60 minutes per day, for all 14 days. That’s enough time to write one idea per day minimum, and maybe up to 5-10+ ideas/jokes daily. Don’t spend more than 1 hour daily on the Challenge idea generation.

If you have more than an hour to spend writing, write other non-Challenge stuff, or work on starting to flesh out first drafts from your peer-vetted ideas.

Or, go hog wild in the comments section and make friends.

Idea generation should be a quick daily ritual. That’s why I say 15 - 60 min max daily!

“If I write, say, two ideas on Monday, does the second one count for Tuesday?”
Hell no. The point of this Challenge is to write something funny every day and build momentum. If you write three headlines, jokes, or premise ideas on Monday, that’s great, and I think you’re great, but it only counts for Monday.

“Will I write full humor pieces in this Challenge? Or full comedy sketches or short stories?”
No. This Challenge is for comedy idea generation. These daily ideas are a cornerstone writing habit for comedy writers. The issue is that many comedy writers don’t have this habit. Many comedy writers are not coming up with fresh ideas every day. That’s a big, fat problem.

I fully expect that you’ll want to flesh out and write some of these comedic premise ideas into drafts, sketches, a stand-up set, etc. You should. But the Challenge itself is about daily idea generation.

“Where or how do I submit my daily Challenge writing?”
This isn’t a writing contest, so there’s no submission to any judges, or anything like that.

You simply do your daily writing, then send your writing for peer feedback using one of the three feedback options. Then you’re done for the day.

• 1 - Comedy Bizarre Writers’ Room (recommended): Get feedback from The Comedy Bizarre Substack comments section in each daily post. You post your ideas, and you’ll get smart reactions and thoughtful feedback from the community here. This is the easiest, most reliable way to get quick feedback from other writers. For paid subscribers (any tier).
  

• 2 - Friend/partner/family (free option): Get a friend, partner or spouse, or family members to commit to giving you daily feedback for 14 days. This is a 100% free and fine option if you’re not a paid subscriber, and if you don’t have an existing comedy writing group.
  

• 3 - Writing group: If you have a comedy writing group, use it. Have your group commit to this Challenge together. (Need a group? I offer twice yearly matchmaking as a perk to paid Founders. The current matchmaking round closes imminently, on Mon, Jan 5. To get a comedy writing group, sign up with the Google form at the very end of this post.)

This peer feedback is an essential part of the process. Don’t skip it!

“I can’t decide: Which feedback option should I choose?”

If you’re not sure and want the default best option, use the Comedy Bizarre comments section. It’s fast, it’s fun, and it works. You’ll get legit feedback from other writers.

If you want to stay free and don’t want to upgrade to paid, that’s fine. The friend method works.

If you want an ongoing comedy writing group in 2026, especially a group to help you workshop drafts, sketches, stories, or stand-up that comes from this Challenge, consider joining a comedy writing group wherever you live, or upgrade to Founder and I’ll matchmake you into a group of other awesome writers.

Note: I wouldn’t join a writing group 100% just for Challenge feedback. A group can provide that, but a group is more about giving you ongoing feedback in the coming weeks and months, as you write comedy.

Keep in mind matchmaking closes this Monday, Jan 5. Last chance—until September.

Here are two subscribers, Jennifer and Tod, on getting feedback…

“Being in an active group of humor writers is awesome. It allows you to experiment and try new things before putting your writing “out there” for all to see. I’ve learned so much and become a better writer thanks to the feedback I’ve gotten and given in the group Alex put together. I highly recommend committing to one to help you become a better and more prolific writer! And honestly, it’s just fun to have a group of writer friends.” - (used the group matchmaking)

“I personally think getting quality feedback is the most important aspect of humor writing. It’s hard to find that in my experience, but with the Challenge you get comments from Alex and everyone else. Through the process of pitching and reacting in real-time, you can quickly identify the keepers.” - (used the comments section)

Want in on the Writers’ Room (comments section), or the group matchmaking? Upgrade here.

Subscribe now

“How does the feedback and accountability line up with my daily output?”
You should send your ideas out for feedback soon after you write them. Like same day or within a couple of days.

If you’re using the friend method, text your friend your idea list and hopefully they reply quickly.

If you’re using the comments section, you post in the comments thread for that day. Your Monday 1/5 writing gets posted in the Monday 1/5 post. Tues 1/6 goes in the Tues 1/6 post. Etc!

One exception or amendment to the above, though: When you get feedback on premise, joke, or sketch ideas, it’s helpful to pitch a list of 3-5 ideas at once, so that your feedback person can pick a favorite.

Therefore, if you’re writing 3-5 ideas daily, great. Just post those daily.

But if you’re only writing one or two ideas daily, that’s fine. Just save those ideas up, and send them for feedback once you have a cluster of 3 to 5 ideas. Personally, I prefer to pitch my premise ideas in groups of 5s—I’ve just found this works well for me.

If you write only one idea for the day, then send that one idea to a friend, and it’s not that funny, it’s harder for them to react helpfully.

But if you send a list of ideas, it’s easier for them simply say, “Hey, I like #4. That’s funny!” And that’s super helpful to you. One of the best parts of comedy idea feedback is just filtering out your top 10-20% ideas, focusing on those, and ignoring everything.

Amateurs try to make everything work. This wastes time.

Pros overgenerate and use only the best.

“If I choose the ‘friend/spouse/etc. free feedback method, is it okay if my friend who’s reviewing my ideas isn’t a writer?”

Yes, this is acceptable.

I’ve previously said I am NOT a fan of friends/family/partners who are not comedy writers giving feedback on your full drafts. I stand by that. Non-writers can give you a lot of confusing notes on your drafts.

But getting feedback on your premise/joke ideas is different. You can simply show your friend/partner/spouse a list of your five jokes for the day and tell them to pick a favorite. That’s it. There’s little room for them to mess you up with confusing feedback.

Of course, if you want a bunch of feedback from other comedy writers, join the comments section. And if you want ongoing feedback on drafts for 2026, get in a writing group. It’s a high value move.

“I’m freaked out by posting my ideas in the comments section though, or I’m freaked out by sharing it with anyone. What if my ideas are sucky and unfunny?”

Don’t freak out. All comedy writers—including professionals—have more bad ideas than good ones. The way to get in the game and get better is to write, hold yourself accountable, and get feedback.

Keep in mind the comment section is private and not accessible on the public web. It’s basically a special writers’ room for Comedy Bizarre people. Everyone there is cool and is just trying to write good stuff. And for anyone who isn’t cool I’ll send some weird drones to take care of them.

Ready to do this Challenge? Any other questions? Ask in the comments section!

See you Monday!

Writing Group Matchmaking: Jan Groups

This is a perk for Comedy Bizarre Founders. To get a comedy writing group, sign up with the Google form at the very end of this post.

On Monday, I announced The 14 Day Comedy Writing Challenge.

The Challenge is a comedy writing habit-builder. You write at least one comedic idea every day for 14 days straight.

The Challenge runs January 5 - 18.

I’ll send you a free Challenge post every weekday—with tips, funny examples, and writing prompts.

Paid subscribers can also post ideas directly in the comments section for feedback, starting Jan 5.

Are you doing the Challenge? Oh, nice, nice. Love to hear it.

Today, I’ll tell you the four things to do now to prepare.

Let’s go!

(Quick note for longtime subscribers not doing the Challenge: You can toggle off Challenge emails only. Go to Settings > Manage subscription > Email notifications and toggle off the Challenge section. Easy to turn back on anytime. Regular Comedy Bizarre posts still land in your inbox as usual.)

Step 0: Subscribe

If you’re already a Comedy Bizarre subscriber, you’ll get all the Challenge posts automatically. If you’re not a subscriber, sign up:

Step 1: Pick a Challenge track

As a Challenger, you pick any one of the four:

• (1) Humor writing: Write at least one comedic headline per day for 14 days. Choose this track if you want to write humor pieces, e.g. those in the style of New Yorker’s Shouts & Murmurs, McSweeney’s, Slackjaw, etc. Also good for humor writers publishing funny stuff on Substack and Medium.

• (2) Sketch comedy: Write at least one comedic sketch premise idea per day. Choose this track if you want to write sketch à la Saturday Night Live, Key & Peele, I Think You Should Leave, or your favorite YouTube sketch comedian.

• (3) Stand-up / One-liners: Write at least one stand-up joke or social media one-liner per day. For stand-up comedians and anyone who wants to drill into pure joke writing.

• (4) Fiction writing: Write one comedic short story premise per day—or funny line of dialogue, for long-form fiction writers. This track is for those who like their comedy in narrative form, especially short stories.

I’ll give all the nitty-gritty details (plus examples) on the Jan. 5 launch day post.

For now, pick your Challenge track. And holler in the comments section with your choice!

Step 2: Pick a feedback path

Getting feedback on your daily ideas is a foundational, high-value habit for comedy writers. Feedback is how you separate the gold from the fool’s gold and focus on your strongest ideas.

That’s why daily feedback is a part of the 14 Day Challenge. You have three options:

• 1 - Comedy Bizarre Writers’ Room (recommended): Get feedback from The Comedy Bizarre Substack comments section in each daily post. You post your ideas, and you’ll get smart reactions and thoughtful feedback from the community here. This is the easiest, most reliable way to get quick feedback from other writers. For paid subscribers (any tier).
  

• 2 - Friend/partner/family (free option): Get a friend, partner or spouse, or family members to commit to giving you daily feedback for 14 days. This is a 100% free and fine option if you’re not a paid subscriber, and if you don’t have an existing comedy writing group.
  

• 3 - Writing group: If you have a comedy writing group, use it. Have your group commit to this Challenge together. (Need a group? I offer twice yearly matchmaking as a perk to paid Founders. The current matchmaking round closes imminently, on Mon, Jan 5. To get a comedy writing group, sign up with the Google form at the very end of this post.)
  

I’ll say more in the Jan 5 launch post. For now, pick your feedback path.

Peer feedback is an essential part of the process. Don’t skip it.

Here are a couple of previous Challengers who used the Writers’ Room (Substack comments)…

“I can’t emphasize enough how helpful I found Comedy Bizarre’s comedy writing challenge. Not only did I end the month with enough creative headlines to kickstart my creativity for weeks, I also met so many humor writers (both beginner and experienced) who gave great feedback and made me feel like part of a community.” - , Subscriber

“Seeing everyone else’s work and commitment really gave me the motivation to keep going. The looming threat of breaking my streak also helped. Now I have a pile of headlines I want to develop and a renewed commitment to staying healthy and living a long life, since I’ll probably need to make it to 100 to finish them all.” - Luís Leal Miranda (), Subscriber

Want in on the Writers’ Room (Substack comments section), or the group matchmaking? Upgrade here.

Subscribe now

Step 3: Commit to your Challenge writing

This idea is straight from the self-help literature on habits, e.g. Atomic Habits. Yeah, it’s basic shit. But what I’m about to say is simple, and it works.

A commitment is easier to follow when you make it precise and write it down.

Write down the exact Challenge writing you’re doing: the when, where, and how of it. Call this your activation statement because that sounds like a cool cyborg thing. Here’s one I’ve used in the past:

I commit to the Humor Writing track of The 14 Day Comedy Writing Challenge.

Every day, from 1/5-1/18, I’ll write one or more headline pitches for a humor piece.

On Monday - Friday, I’ll spend 20 minutes per day, right after breakfast, at my kitchen counter writing headline ideas in my journal. On Sat/Sun I’ll spend 45 minutes at La Tazza around noon, writing headline ideas on my laptop.

You can use my statement as a template for yours. Be sure to actually write yours down: in a document, a notes app, a journal, or whatever.

The Challenge will go down smooth if you budget your daily writing time in advance.

How much time to budget for this Challenge? About 15 - 60 minutes daily:

• 15 minutes per day: Enough time to sit down, focus, get in a “mini flow state” and come up with one or two comedic ideas. You could do this during a work break, on a park bench during a walk, during a quiet moment before work. Every writer can find 15 minutes a day.

• 30 minutes per day: Sweet spot. Plenty of time to come up with 3 to 5 funny ideas daily. My recommendation: Block off 30 minutes per day for the Challenge.

• 60 minutes per day: You’re flying high. An hour per day means you will crush this challenge and you’ll probably write 100+ ideas over the 14 days.

Remember, you can write more than 1 idea per day, but 1 is the minimum. So, pick a reasonable time commitment, block it in your calendar, and write your commitment!

Step 4: Bookmark The Challenge

You can always find All Challenge Posts here.

Bookmark it so you don’t miss any posts!

Next steps…

I’ll send you a final pre-launch post on Saturday. Then we get started on Monday.

Mark your calendar for Jan 5 - Jan 18.

Write four sticky note reminders and slap them on your forearms. I recommend two sticky notes per arm, but three and one could also work. I’m not here to tell you how to distribute your four sticky notes—that’s up to you.

And if you want to do writing group matchmaking, remember that it closes Monday.

Writing Group Matchmaking: Jan Groups

This is a perk for Comedy Bizarre Founders. To get a comedy writing group, sign up with the Google form at the very end of this post.

Ready to do some daily comedy writing in 2026?

The 14 Day Comedy Writing Challenge starts next Monday, Jan 5.

It runs here on Comedy Bizarre from January 5 - January 18.

This is the pre-launch week where I tell you what to expect and how to prepare.

I designed this Challenge as a kickstart for your daily funny writing habit.

I’ve carefully refined the Challenge through iteration, feedback, meditation, and coded messages delivered by robed figures who chanted at me in a strange tongue that gave me really weird dreams.

I’m psyched for you to join.

All posts (instructions, tips, prompts, etc ) will be free posts.

The comments section (aka the Comedy Bizarre Writers’ Room) will be for paid subscribers. More on that below.

If you got this post in your email inbox, you’re in.

If not, what in the dickens are you waiting for? Sign up here.

Here’s what you need to know about The Challenge…

(Quick note for longtime subscribers not doing the Challenge: You can toggle off Challenge emails only. Go to Settings > Manage subscription > Email notifications and toggle off the Challenge section. Easy to turn back on anytime. Regular Comedy Bizarre posts still land in your inbox as usual.)

Four Challenge Tracks

As a Challenger, you pick any of the four.

• (1) Humor writing: Write at least one comedic headline per day for 14 days. Choose this track if you want to write humor pieces, e.g. those in the style of New Yorker’s Shouts & Murmurs, McSweeney’s, Slackjaw, etc. Also good for humor writers publishing funny stuff on Substack and Medium.

• (2) Sketch comedy: Write at least one comedic sketch premise idea per day. Choose this track if you want to write sketch à la Saturday Night Live, Key & Peele, I Think You Should Leave, or your favorite YouTube sketch comedians.

• (3) Stand-up / One-liners: Write at least one stand-up joke or social media one-liner per day. For stand-up comedians and anyone who wants to drill into pure joke writing.

• (4) Fiction writing: Write one comedic short story premise per day—or funny line of dialogue, for long-form fiction writers. This track is for those who like their comedy in narrative form, especially short stories.

You can write more than one idea daily, but one new idea daily is the minimum. I’ll explain the exact details, and what each track entails, in the first Challenge post on Monday morning, January 5th.

For now, think about which track you’ll choose: Which style of comedy is your path?

Why Daily Idea Generation?

Why the focus on these simple, daily comedy ideas? Several reasons:

• Simplicity and low friction: Writing one idea per day (minimum) is low friction. You can do it in ten minutes or so. It’s hard to make excuses.

• Consistency: By doing the same, simple comedic exercise each day, you get consistent daily writing done.

• Momentum: Writing at least a little something funny every day builds a habit. Psychology nerds can argue about when a “habit really forms” but 14 days nonstop is a great start.

• Volume: You will build a surprisingly large volume of good, funny ideas. Remember, Quantity Wins. When you write daily, the wins stack up.

• Premise = half the battle. A clear, funny premise is half the battle in making great comedy. The more solid premise ideas you have, the more prolific and successful you’ll be.

• Idea feedback = smart vetting. Simple premise or joke ideas are how you vet your comedic ideas with feedback. You can get feedback to make sure you’re on the right track before you commit to writing an entire piece, story, sketch, or routine. This is the smart way to do comedy.

In short, daily idea generation is a foundational writing habit for every comedy writer.

Commit to daily idea generation and your comedy writing life will be far richer. The robed figures who showed up at my doorstep told me so, my dreams reiterated it, and my experience as comedy writer has confirmed it again and again. Would you argue with that? Not wise!

Challenge Posting Schedule

I’ll send you one free post every weekday (Monday - Friday), from Jan 5 - Jan 16.

Ten posts total. Then a wrap-up post on Jan 19. Posts will arrive in your inbox every morning.

I’ll also send out a weekend post on both Saturdays that’s just a comments section (nothing else) for those of you participating in the Comedy Bizarre Writers’ Room. That way those of you using the comments section have a place to post your Saturday/Sunday ideas.

Daily posts will have:

• Advice: A practical comedy writing tip that you can apply to that day’s writing.

• Inspirational examples: A daily humor piece, comedy sketch, stand-up bit, or short story that I like. You don’t have to read/watch these, but it helps. Load your brain with great writing.

• A writing prompt: These were popular last time, so I’m bringing them back. A daily, offbeat prompt to inspire your writing for that day. You’re free to ignore these and write about whatever you want.

• Accountability (Writers’ Room comments section): A Substack comments section for paid subscribers who want to get their feedback from our community here.
  

Again, all posts are free. If you’re a free subscriber you can do the full Challenge.

However, the comments section (the Comedy Bizarre Writers’ Room) is paywalled.

Access that by upgrading to a paid subscription (any tier) here.

Subscribe now

That said, there’s more than one way to get feedback…

Feedback is Fundamental

Feedback on your daily ideas is a core part of this Challenge.

Peer feedback is what helps you find your gold nugget ideas in a stream of possibilities.

Some of your ideas will simply leap out as stronger and smarter, and some quick external feedback from someone of good taste will reveal this.

Here are your three options.

• 1 - Comedy Bizarre Writers’ Room (recommended option): Get feedback from The Comedy Bizarre Substack comments section. Posts have a comments section for daily feedback. You post your ideas, and you’ll get smart reactions and thoughtful feedback from the community here. This is the easiest, most reliable way to get immediate feedback from other writers who know what’s up. For paid subscribers (any tier).
  

• 2 - Friend/partner/family (free option): Get a friend, partner or spouse, or family members to commit to giving you quick, daily feedback for 14 days. This is a totally free option if you’re not a paid subscriber, and if you don’t have an existing comedy writing group. Simply text/WhatsApp/email them your daily ideas, and have them react. More to come on this on the Monday, Jan. 5 launch post.
  

• 3 - Writing group: Get feedback from your writing group. If you have a comedy writing group, buy all means use it. Have your group commit to this Challenge together. (Need a group? I offer twice yearly matchmaking as a perk to paid Founders. The current matchmaking round closes Mon, Jan 5. To get a comedy writing group, sign up with the Google form at the very end of this post.)

Go with any of these three options. They all work. However, choose one of them.

Some people have asked me, “how do I submit my daily writing in the Challenge?” The answer is: By getting feedback. This isn’t a writing contest, so there’s no submission to me, or to any judges, or anything like that.

You do your daily writing, then send your writing for feedback using one of the three options above. Then you’re done for the day.

If you’re not sure which feedback option to go with, I recommend joining the Substack Comments section.

It’s not only fun and fast, you’ll get a lot out of seeing the ideas everyone else posts and how other people react to them.

And you’ll get a lot out of commenting on people’s ideas. This forces you to think about what works and doesn’t work. It builds your comedy brain.

Here are two reactions from past Challengers who used the comments section…

“Hi Alex, just thought you might like to know that the piece I workshopped during your [last] Challenge was just published by Points in Case. Thanks for providing the forum and for all the solid tips. Cheers!” - , Comedy Bizarre paid subscriber

“I loved the incentive to think of headlines every day... I also liked seeing what other people came up with, and the process of giving and receiving feedback - very helpful! I would definitely participate in this exact same type of challenge again.” - , Comedy Bizarre paid subscriber

Sample published pieces from past Challenge

Pitched in the Comedy Bizarre comments section!

• Analogies Are The Rolls-Royce Of Comparisons (Slackjaw) by . - Selected by Luke Burns and James Folta as a favorite humor piece in A Newsletter of Humorous Writing
  

• This Chuck-E-Cheese Will No Longer Offer an “Animal Style” Option on a Secret Birthday Celebration Menu (Points in Case) by

Feedback options — tl;dr

• Free option: Get friend feedback. It’s fine. I’ll give you tips to optimize.

• Writers’ Room comments section: This option slaps. Upgrade to any paid tier.

• Writing group matchmaking: Use your own group. Or, I’ll put you in a group. Upgrade to Founder.

Want in on the Writers’ Room (comments section), or the group matchmaking? Don’t miss out. Upgrade here.

Subscribe now

Next steps…

I’ll send you a post on Thursday, Jan 1 with a few steps to prepare for The Challenge.

Beyond that, mark your calendar for Jan 5 - Jan 18, or write a sticky note and tape it to your mirror, or chalk up your driveway with a bold reminder.

If you’re doing this Challenge and participating in the Writers’ Room (comments section) this round, drop a comment and let me know!

Writing Group Matchmaking: Jan Groups

This is a perk for Comedy Bizarre Founders. To get a comedy writing group, sign up with the Google form at the very end of this post.

Welcome to the final day of the 10 Day Humor Writing Challenge!

If you’re catching up, you can find all Challenge posts here.

So far, here’s what we’ve done:

• A vetted headline premise for your humor piece—see Day 1 post

• A list of 10-15 jokes + joke feedback—see Day 1 and Day 3 posts

• A rough draft + feedback—See Day 5 post

• A rewrite + feedback—See Day 8 post

Today is all about getting your draft across the finish line.

Make that draft a final draft, then ship it!

But first, how do we know when this turkey’s fully cooked?

Step 1: Figure out how much more editing your piece needs

At this point, if all went to plan, have a second or third draft. We want to figure out how much more editing it needs before it’s a final draft.

Read more

Welcome to Day 8 of the 10 Day Humor Writing Challenge.

We’re in the home stretch.

If you’re catching up, you can find all Challenge posts here.

To recap, if you’ve been doing this Challenge, here’s what you should have so far.

• A vetted headline premise for your humor piece—see Day 1 post

• A list of 10-15 jokes + joke feedback—see Day 1 and Day 3 posts

• A rough draft + feedback—See Day 5 post

Today is all about rewriting your first draft into a tighter, funnier second draft.

How do you do that? Which edits should you target?

Well, the feedback that you (hopefully) got over the weekend should tell you a lot.

I said in Friday’s post that, at the risk of oversimplifying, feedback boils down to this: “What’s funny here that I should keep, or do more of?” and “What’s not funny here? What should I cut?”

You almost always need to revise and rework your humor draft, sometimes multiple times.

It’s rare that a first draft gets it right.

In my deep dive The 21 Most Common Humor Writing Mistakes, I said the main revisions in a humor draft can include:

• Structural changes to get the flow and the comedic escalation right

• Cutting the chaff (the less funny parts)

• Cutting the parts that are off-premise

• Simplifying and trimming out unneeded complexity

• Rewriting to make your individual jokes funnier

• Tweaking or adding specifics to make things clearer or to make the details funnier

And I should probably add:

• Doing more of what’s already working, or escalating it even harder.

Read more

Welcome to day 5 of the 10 Day Humor Writing Challenge!

Today, our foundational work with headline and joke writing will pay off: we move into writing a full draft.

If you’re catching up, you can find all Challenge posts here.

To recap, if you’ve been doing this Challenge, here’s what you should have so far.

• A vetted headline premise for your humor piece—see Day 1 post

• A list of 10-15 or so jokes—see Day 1 and Day 3 posts

• The first third or so of your draft (around 100-300 words)—See Day 3 post.

If you’re playing catch-up, you can nail those things in a couple hours or so.

If you’re all up to speed, onward!

I say that writing a first draft couldn’t have lower stakes.

That’s sort of an exaggeration, but it has a kernel of truth.

One, your first draft will probably never be published or submitted anywhere. It’s just your first try at exploring your premise. You have as many rewrites as you please to polish it up and get it right for publication. Low stakes!

Read more