back to posts

Writing Well, Cheat Sheet by Julian Shapiro

Writing Well: Cheat Sheet

Updates from Julian Shapiro

Updates to this guide are posted on Twitter.

Keep learning

Choose a topic

Write your intro, and use it to brainstorm talking points

Get feedback on your intro

Create a starting outline

Explore talking points within your outline

Rewrite for clarity, succinctness, and intrigue

Cycle between rewriting, resting, and receiving feedback

Copy edit for grammar, word choice, and flow


Open people’s eyes by proving the status quo wrong.

Articulate something everyone’s thinking about but no one is saying. Cut through the noise.

Identify key trends on a topic. The use them to predict the future.

Contribute original insights to a field through your research and experimentation.

Distill an overwhelming topic into something approachable.

Share a solution to a tough problem.

Tell a suspenseful and emotional story that imparts a lesson.


Does writing this article get a weight off your chest?

Does it help you reason through a nagging, unsolved problem of yours?

Does it persuade others to do something you believe is critically important?

Do you obsess over the topic and want others to geek out on it too?


Start your brainstorming process by prematurely writing your intro. In discovering how to make your intro interesting to you, you'll also discover how to interest and hook readers.

Hooks are half-told stories. Tease something fascinating, but don’t fully reveal the details.

How to generate hooks: (1) Ask yourself, “If someone else wrote my intro, what are the most captivating questions they could pose to make me excited to read this?” (2) Write those questions down. Even if you lack the answers. (3) Rank your questions by how much they interest you. (4) The top questions become your hooks: Pose them in your intro and don't reveal their answers.

Ask others for feedback after you've written your intro. Sanity check your hooks.

If feedback-givers have skepticisms, proactively address them in your intro. And if they have other questions they care about, swap them in if they captivate you too.

Browse the list of skepticisms and their solutions here.

First draft steps

Choose an objective for your post.

Write a messy braindump of your ideas.

Transfer your best talking points to an outline. Use supporting points and resulting points: what is needed to make your argument, and what are the implications of your argument being true?

Write your first draft using that outline.

First draft writing process

Your talking points come from hooks, experience, research, experiments, brainstorming, and mental models.

When ideas stop flowing, ask yourself: How can I make my point more convincing? What are the interesting implications of what I just said?

Be self-indulgent. You are a proxy for your reader. What interests and surprises you will interest and surprise them.

To generate surprise, use Graham’s Method: First, learn all the basics on a topic. Then, if you can find new information that surprises even your knowledgeable self, it’ll surprise laypeople too.

Outros should frame why your article was worth reading. Share a poignant takeaway that summarizes the article's wisdom, and tell readers where they can go to continue the journey they started with you.


If you imagine you're writing for an audience of thirteen-year-olds, you'll think and write more clearly.

Use simple wording and focus on one idea per sentence. Remove grammatical overhead.

Provide examples and counterexamples when simplified language isn’t enough to achieve clarity.


Rewrite sections from memory. Focus on the key points and let the fluff fall away.

Then remove unnecessary words from each paragraph.

Then rephrase paragraphs to be as succinct as possible.


The trifecta of intrigue: 1. A captivating intro. 2. A section of intense surprise or insight. 3. An ending that satisfyingly justifies why the piece was worth reading.

Ask feedback-givers to highlight every sentence that gives them a dopamine hit — the little moments of "that was interesting." For each hit, increase a counter at the end of the corresponding sentence. Like this (3). If there are sections without dopamine hits, make those sections shorter or inject more insight and surprise into them.


Ask readers to score your writing from 1 to 10. Aim for 7.5+.

Use your future self as a source of feedback. Take breaks to defamiliarize yourself.


An authentic voice resonates best with readers: your way of speaking, interests, and perspectives on the world are a breath of fresh air.

Shed the style you’ve absorbed from others. Write nonfiction the way you sound.

Optionally incorporate multimedia, anecdotes, analogies, and humor to reinforce your points and to entertain.


Optionally learn to punctuate with my companion post.

Use paragraphs of five sentences or fewer. This cushions paragraphs with white space, reducing the perceived reading workload. Short paragraphs also provide readers more opportunities to pause and reflect on your ideas.

Use verbs that embed the meaning of their adverbs. For example, “She spoke loudly” could be “She shouted.”

Only use adjectives and adverbs if they add important details.


Practice by writing persuasive essays. This helps you focus on improving (A) the quality of your thinking and (B) your eye for rewriting. Try writing posts that persuade your friends to change their minds.

Ask them to score how much your writing sustained their interest.

Keep learning

Read my other in-depth guides and blog posts.

Say hello on Twitter.

You are receiving this email because you opted in on

Our mailing address is:

Julian Shapiro

San Francisco

San Francisco, CA 94110

Add us to your address book

You can update your preferences or unsubscribe from this list.

If you found it useful, please consider signing up to my newsletter. Every week, I share my thoughts on cool stuff I found around the internet. No spam, ever. Unsubscribe any time.