Slackjaw Humor Writing Challenge 2020 — The Rules!

How to complete The Challenge…

Alex Baia
7 min readMar 24, 2020

Welcome! You have from now until April 30, to pitch, write, re-write, and submit your entry. We’ll support you with resources, encouragement (via your opt-in email), and an awesome Facebook community. It will be a blast.

Ready to write? Let’s do this.

Real quick: BOOKMARK THIS PAGE. DON’T LOSE IT.

Resources

First, a few resources you might like…

0. Overview: What you will submit to enter

Your challenge submission will contain all and only these things:

  • Your headline (this is the title of your piece).
  • Your 300–800 word final draft (this is your entry).
  • Your first rough draft (be sure to save it).
  • Your list of 5–10 humor headline ideas.

Keep in mind:

  • Your piece can be in any format: a monologue or speech, a list or listicle, a letter or email, a literary dialogue, a straightforward article or essay, etc.
  • No topical pieces (e.g. no coronavirus), and no fake-news Onion-style pieces.
  • You can only send one entry! And it must be single-authored (no co-authored pieces).
  • Read all the way to the end for exact instructions on where and how to send us your entry.

Now let’s dig into the writing process.

1. Write your headline ideas

A headline is the title of your humor piece. Your first task is to brainstorm a big list of funny headlines that you could write out as full pieces.

Your headline list will look like this. We’ll use the Top 10 finalist pieces from last year’s Challenge as examples:

  1. Ernest Hemingway At The Taco Bell Cantina.
  2. New — It’s Adjunct Barbie™!
  3. My Kids: RANKED!
  4. This Song Sucks Ass: A Line By Line Analysis Of “Take Me Out To The Ball Game” And How I’d Fix It.
  5. We’re Pleased To Offer Your Brand The Opportunity To Align With Jesse’s Momentous Gallbladder Removal
  6. Replies To Yelp Reviews Of My Hedge Maze
  7. Research Participants Wanted (To Beat My Ass)
  8. I Order The Supplies In My Office, And I Am Drunk With Power
  9. The Future Of Education Is An Interactive Laptop Screen That Destroys All Hope And Joy
  10. I’m Your About-To-Be-Born Baby, And Here’s All The Ways My Birth Will Terrify You Two Idiots

Etc! You can and should write more than 10 ideas initially.

Check out all of last year’s winners and honorable mentions here.

In short, you are just brainstorming a list of headlines — nothing more! Each headline should do two things:

  • It should be funny or interesting. It should make your reader want to click on it.
  • It should reveal a clear comedic premise. In reading your headline, your readers should have a clear idea of what your piece is about and why reading it would be an enjoyable use of their time.

Evergreen headlines only: no topical, no coronavirus!

For this Challenge, all headlines (and all final submissions) must be evergreen humor. Evergreen just means your idea will be funny for a while to come. Ask yourself: “Will this piece still be funny and relevant in 1 or 2 years?” As a consequence of this, no headlines or stories about coronavirus, or any other topical event.

Other tips:

  • Come up with as many headlines as you can. Ten headlines is nice but twenty is nicer. Thirty is impressive. Fifty headlines? Now you’re getting somewhere. Quantity leads to quality here.
  • Vague or boring headlines are the enemy. Make your headlines sound like something that will bring a laugh, not something out of The Economist or your dad’s fishing magazine. (No offense to those fine periodicals.)
  • When writing headlines, have fun. Turn off the editor in your brain and just write a lot without judging.
  • Remember, go for evergreen humor ideas and avoid timely/topical ideas.
  • After you’ve created a long list of headlines, now pick your favorite 5–10 headlines.
  • At this point, you’ve written nothing other than headlines.

Okay, do you have your list of your favorite 5–10 titles/headlines to pitch?Then move to the next step!

2. Pitch your headlines for peer feedback

Now it’s time to pick your funniest evergreen humor headlines, based on peer feedback. This feedback is essential since it gets you outside your head and simulates how your audience will react to your headlines.

There are two ways to pitch your headlines:

  1. Join Flapjaw: Slackjaw’s Facebook Group for Writers and pitch your 5–10 headlines here. This group exists for the Slackjaw writing community (that includes you now!), and you can go in here and pitch your headlines as a Facebook poll in this group. People will vote on which title they prefer. Instant, easy feedback.
  2. (FRIEND OPTION) If you’re not on Facebook, or you just don’t want to join the Slackjaw group, no sweat. Send your 5–10 headlines to a friend, or a few friends, and ask them which title or titles they like the best.

While you’re not obligated to go with the headline that the group selects as funniest, you should take this feedback seriously. In a poll of 10 headlines, you should almost certainly go with a headline that makes the top 2 or 3.

Got your winning headline? Great. That’s your Challenge piece.

But hang on to the rest of your 5–10 headlines — you’ll need them in the end.

3. Draft your piece using your funniest headline

Now it’s time to write your piece. The piece that you submit as your Challenge entry must be:

  • 300–800 words.
  • A premise-driven, evergreen humor piece, like the ones linked above in section 1.
  • Your piece can be in any format: a monologue or speech, a list or listicle, a letter or open letter or email, a literary dialogue, a straightforward article or essay, etc.
  • The piece should not be a fake-news style (Onion-style) piece, a sketch or screenplay, or a poem.

Work on your draft — and re-work it as much as you like — until you’re relatively happy with it. It’s fine to do a few rounds of re-writing before you show it to anyone. But don’t obsess about this, or fall into despair if it’s not perfect. Write something that’s good enough.

4. Share your draft with a friend or writing partner

Okay, you’ve got your draft.

Now it’s time to get feedback from any writing partner or friend of yours.

If you’d like help finding a feedback partner, we’ll have a thread for that on Flapjaw: Slackjaw’s Facebook Group for Writers.

It’s fine to get feedback from multiple people. You may even want to have a small group of feedback partners where you all critique each other’s pieces. Up to you!

Here are some questions to bring up when getting peer feedback on your draft:

  • Was the premise (main idea) of my piece clear? Did you understand what I was trying to do?
  • Was anything in the piece unclear or confusing?
  • Was the comedic premise and Point-of-View in this piece 100% consistent?
  • Were there any parts you especially found funny, or things you liked that you thought I should do more of?
  • Were there any parts that weren’t as funny that you think I should cut?

Here’s a more detailed guide to giving and receiving feedback that sarah james has put together.

Hint: It can be helpful to share either a Medium draft or a Google doc (with comment permissions turned on), since these both let your feedback partner comment inline, directly on your draft.

5. Re-write your draft based on your peer feedback

Take all of the peer feedback you got on your draft, and use it to polish your piece into the clearest, strongest, funniest, piece of humor writing you can.

6. Send in your submission!

Got your final draft? Now submit your challenge entry to Slackjaw. Please follow these directions carefully.

  • E-mail your entry to slackjawsubmissions@gmail.com
  • Use the exact subject line ‘Slackjaw Challenge 2020: [Full Name]’ where [Full Name] is replaced with your name.

Your email must contain all and only these things, in this order:

  • Your name, email address, and twitter handle (if you have one)
  • The title of your Challenge entry piece
  • A hyperlink to your final draft, in the form of an unpublished Medium draft.
  • A list of all your 5–10 headlines in plain text
  • Your original rough draft pasted in plain text

Your email should have no attachments and no links other than one link to your Medium draft.

Fine print

Your Challenge entry email should look like this:

Subject: Slackjaw Challenge 2020: Jane Smith

Jane Smith
email.address@provider.com
@twitter_handle

  1. My Funny Humor Piece Headline
  2. Here’s my entry: https://medium.com/@you/your-entry
  3. Here’s my list of 5–10 funny headlines…
  4. Here’s my original rough draft, pasted here as plain text.

Challenge closes April 30th at 11:59 pm Central. Be sure to send your Challenge entry before then!

Reminder: your piece should be 300–800 words. And you can only send one entry!

We plan to announce the winners on Slackjaw, and via email, by early May.

And that’s everything! Happy writing.

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Alex Baia

Humor writer, book junkie, stargazer, optimist. Resident philosophy major. Get my humor newsletter: https://alexbaia.com/humor