My Writing Checklist

I've taken Write of Passage 3 times. First as a student, then as a mentor, lastly as an editor.

Every single time my mind was blown away by how much my writing improved in so little time.

Here's the checklist I now go under every time I finish a piece. Often, I'll even pass it to my AI editor as context so that it makes sure to answer all these questions and edit the article in the best way!

Thank you David Perell and team for the valuable insights! WoP will be missed!

The Writing Checklist

1. Is this article written by an architect or an archeologist?

This is a simple framework for you to better understand who you are as a writer.

Architects know exactly what they want to write about. They have a specific topic burning a hole in their brain: AGI, tech strategy, alternative education, regenerative agriculture — you name it. Architects are intentional, goal-oriented specialists. If this resonates with you, then double-down on your expertise.

Archaeologists want to write about anything and everything, all at the same time. They can’t possibly pick one topic, because they’re infatuated by them all. Archaeologists are intuitive, adventurous polymaths. If this resonates with you, then follow your curiosities to find what’s valuable.

2. What’s the article’s anchor?

• Hard-Won Wisdom: An experience that taught you a lesson.
• Domain Expertise: Something you know more about than most people.
• Enduring Obsessions: Something you’ve always loved to do: passions, hobbies, unique idiosyncrasies galore.
• A Personal Anecdote: A story about yourself that defines the storyline
• A Quote: A phrase that shaped your thinking about a topic.
• A Fact or Statistic: A data point that tells a story.

3. Are you reaching beyond consensus?

Which familiar insight are you giving a novel fresh and novel frame?

“Start right before you get eaten by the bear.” Same idea, different frame.

4. What’s the shiny dime you’re trying to get across?

Your Shiny Dime is the central idea of your piece, the axis on which every sentence turns. It’s one main idea. Not two. Not three. Not fifteen. One. And this idea doesn’t need to be earth-shattering. It needs to be specific and surprising.

• Specific: Zoomed-in and high-definition. Instead of writing a generic essay about Disney World, write a hyper-specific essay about how the New Orleans Square does or doesn’t feel like New Orleans.
• Surprising: Fresh and novel. Think back to reaching beyond consensus. Instead of writing a typical piece about tech strategy, tell a seemingly unrelated story and then connect the dots. Catch your reader off guard and make them think, “Whoa, I’ve never thought of it like that before.”

5. Where does your writing POP?

POP Writing is the antidote to boring writing. Highlight the places in your article that are personal, observational, and playful.

• Personal: Relate to your reader.
  • Tell a story. Share a personal experience that paints a picture.
  • Show emotion. Reveal your authentic self.
• Observational: Teach your reader.
  • Use an example. Ground the lesson in a memorable anecdote or analogy.
  • Make it actionable. Give your reader a clear next step.
• Playful: Dazzle your reader.
  • Experiment with style. Surprise your reader with crafty sentences.
  • Delight with word choice. Use familiar words in uncanny ways.

6. How much of your article is minimalist vs maximalist?

All writing exists on a spectrum between minimalism and maximalism. Master both in the same piece to make your writing distinct.

• Minimalism is about clarity, concision, and directness. Think of writing styles like Ernest Hemingway, Derek Sivers, or Brenee Brown.
  • Done right, minimalism communicates an idea as clearly as possible, using writing as a tool to drive home a point.
  • Done wrong, minimalism becomes beige and cookie-cutter. (But you can avoid that trap by using POP Writing.)
  • With minimalism, you're conveying information with literal language.
• Maximalism is about detail, vibrancy, and expression. Think of writing styles like David Foster Wallace, Quentin Tarantino, or Gregory David Roberts.
  • Done right, maximalism evokes emotion and transports readers to a new place. It’s less about the efficiency of an idea and more about creating an environment for your reader to inhabit.
  • Done wrong, maximalism becomes over-inflated, purple prose. (But you can avoid that trap by narrowing the scope and focusing on your Shiny Dime.)
  • With maximalism, you're creating a feeling with figurative language.

7. If your writing is music, where is the bigger emphasis being placed?

Vary sentence length for to write music. Your sentences must have rhythm.

If you have mostly long sentences, the short ones provide emphasis. The inverse is also true.

8. What areas of your article are CRIBS?

• ‍Confusing: Clear writing transfers ideas efficiently from writer to reader. Writing becomes confusing when authors try to sound clever instead of being clear.
  Next step: Replace complex words with simple ones. If you're still unclear, simplify your ideas first.‍
• Repeated: Good writing is concise. Repetition wastes the reader's time and suggests you didn't express yourself clearly the first time.
  Next step: Delete the repetitive parts.‍
• Interesting: Great writing combines insight with entertainment. It either comforts the confused or confuses the comforted.
  Next step: Expand on your most interesting ideas.‍
• Boring: Readers leave when bored. Ask your editor which sections made their mind wander.
  Next step: Delete boring ideas. Rewrite boring delivery.‍
• Surprising: Break your reader's mental model by telling them something unexpected. New but unsurprising ideas are trivial.
  Next step: Keep only the surprising parts. Build suspense before revealing them.

9. What’s the architecture of your essay?

• Idea: circle of information
  • Material: all the evidence supporting your idea
  • Thesis: the key message, shiny dime you want to get across
  • Title: Compressing the thesis into a catchy phrase to engage the reader
• Form: the storyline
  • Story: builds tension to keep the reader forward
    1. Build a hook, question, and answer into the draft to build tension. Shiny dime may be posed as a question then clearly stated as the answer‍
  • Structure: orienting themes so you’re never confused‍
  • Flow: How to loop from paragraph to paragraph so the story flows‍
• Voice: texture that runs through the line‍
  • Spirit: personality behind the page, tone
    • Highlight phrases that have personality so you can highlight the gaps. where is the humor? where am I serious/sad?‍
  • Sound: about rhythm, rhymes and repetition‍
  • Sight: imagery, visuals, and context

10. Is it a story-led or argument-led article?

Think about whether your article is story-led or argument led.

• Story-Led Essays entertain your reader. Here's the flow:
  1. Promise: What will change by the end?
  2. Progress: What tension/conflicts arise? What happens?
  3. Payoff: What has changed?
• Argument-Led Essays persuade your reader. Here's the flow:
  1. Claim: What idea do you want your reader to believe?
  2. Evidence: What statistics/data/examples support your claim?
  3. Takeaway: What idea do you want your reader to remember?

Then, figure out where you can add the opposites.

I.e. if your article is story-led, add some arguments. If your article is argument-led, add some stories.

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