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The Writing Well Handbook

Our goal

This handbook helps you write nonfiction books and blogs.

What is writing?

Writing is the pursuit of thinking clearly with the help of paper. Writing slows down your thinking so you can dance with your ideas.

If people cannot write well, they cannot think well. And if they cannot think well, others will do their thinking for them.
—George Orwell

Why write nonfiction?

1. Clarity

Great minds became brilliant through communication. Great ideas emerge while writing or speaking—not before. When you express ideas, your brain can't help but to draw connections between them and advance them.

Writing is a laxative for the mind.

2. Leverage

Keeping thoughts to yourself is a disservice to others. If you have something important to say and you say it well, you send strangers down paths badly needed.

As history has shown, a writer can change the world from their couch. Writing is the most radical thing you can do without spending a dollar.

3. Connection

The most efficient way to meet interesting people is to become someone they already want to meet.

One way to do that is by doing cool things, writing about them, then getting the word out. Or podcast. Or vlog.

Whenever you distribute content with an authentic voice, similarly-minded people want to meet the person behind that voice.

What you'll learn

Together, we'll deconstruct any topic you want to write about. You'll learn to write plus rewrite your thoughts so that they're interesting, substantitive, and resonant.

  • Page 1: Ideas — Identify what to write about
  • Page 2: First Drafts — Generate insights on your topic
  • Page 3: Rewriting — Rewrite for clarity, intrigue, and succinctness
  • Page 4: Style — Rewrite for style and flow
  • Page 5: Practicing — Work toward mastery

I’ll provide a cheatsheet on the last page of this handbook, but I recommend taking notes. Doing so forces you to slow down and draw connections between ideas. This helps you internalize them. Reading without note-taking is like exploring new territory without drawing a map.

Tip — See the bottom of your screen for quick navigation links.

Who should read this?

This handbook is for:

  1. Advanced nonfiction writers wanting to improve their craft: You’ll encounter unique insights to better understand how exceptional writing works.
  2. Aspiring writers who fear publishing online: This handbook should increase your confidence. We'll overcome key blockers together.

Over the next 30 minutes, you'll become a much more deliberate writer. There's a science to nonfiction writing that many haven't realized.

Who's Julian Shapiro?

I spend thousands of hours deconstructing topics that interest me. I compile my insights into handbooks (like this one). Over a million people read them annually.

Readers like my writing for its density of insights and efficiency.

I also write threads on Twitter , which are read by over a million people per month. They're consistently among the most viral long-form content on Twitter.

Before this, I wrote a column for the largest tech news site, TechCrunch. And I authored a boring programming book for Pearson Education.

You can learn more about me on my about page .

Learn how to write well. Topics include figuring out what to write about, how to write an introduction, the writing process, writing style, and copyediting.

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How to source writing ideas

Our goal

This page covers:

  • Finding the best ideas to write about—for blog posts, essays, and articles
  • Finding the most interesting direction to go in
  • Writing an intro that compels readers to continue reading

What makes nonfiction good

People read nonfiction to learn and to feel. My framework for ensuring a blog post accomplishes both is to start with a first draft that focuses on "novel" ideas.

A novel idea is one that's not just new to the reader, but also significant and not easily intuited. Think of it as new and worthwhile . There are five novelty categories:

  • Counter-intuitive — "Oh, I never realized the world worked that way."
  • Counter-narrative — "Wow, that's not how I was told the world worked!"
  • Shock and awe — "That's crazy. I would have never believed it."
  • Elegant articulations — "Beautiful. I couldn't have said it better myself."
  • Make someone feel seen — "Yes! That's exactly how I feel!"

Novelty is what gives readers dopamine hits. You find novel ideas by pursuing your curiosity and noting what interests and surprises you along the way. If it intrigues you, it'll likely intrigue your readers too.

In drafts two and beyond, I then rewrite these novel ideas to make them resonate . Resonance is when ideas take root in readers' minds. It's the art of capturing their imaginations and relating to their life experiences so that they feel .

Ideas resonate when they're wrapped in:

  • Stories
  • Analogies
  • Examples
  • Authentic voice

In other words:

Writing Quality = Novelty x Resonance

That's my writing framework.

And it starts with choosing your topic.

1. Choose your topic

The best topic to write about is the one you can’t not write about. It’s the idea bouncing around your head that compels you to get to the bottom of it.

Sometimes, this means the ideal place to start is thinking through what bothers you most. Write a post to work through that—because the best writing is often therapy that you publish for the world to learn from.

Here's what that looks like in practice. Step one is choosing an objective for your post, such as:

  1. Open people’s eyes by proving the status quo wrong.
  2. Articulate something everyone’s thinking about but no one is saying. Cut through the noise.
  3. Identify key trends on a topic. Use them to predict the future.
  4. Contribute original insights through research and experimentation.
  5. Distill an overwhelming topic into something approachable. (This guide.)
  6. Share a solution to a tough problem.
  7. Tell a suspenseful and emotional story that imparts a lesson.

Step two is pairing that objective with what motivates you:

  1. Does writing this article get something off your chest?
  2. Does it help reason through a nagging, unsolved problem you have?
  3. Does it persuade others to do something you believe is important?
  4. Do you obsess over the topic and want others to geek out over it too?

Your objective clarifies what you're trying to accomplish, and your motivation ensures you actually see it through.

That’s all that's needed to write with conviction: pair an objective with a motivation. When writers lack one of these, they tend to not finish their articles.

If the right objective and motivation combo isn't coming right away, that's okay. Start writing like you would in a diary to uncover what's in the back of your head. As you write, a clear objective will eventually emerge. At that time, do a full rewrite with your clear objective as your guiding light.

Once you've chosen what to write about, the next step is uncovering what to say.

It's not that I'm so smart. It's just that I stay with problems longer.
—Albert Einstein

2. Write an intro

My process begins with writing an intro because intros help me find novel ideas.

I define an intro as the minimal information necessary to:

  • Introduce the breadth of the post's contents so that readers can decide if it's for them.
  • Hook readers into reading more.

It doesn’t matter how you hook readers, so long as you eventually fulfill the hook.

A hook is not a gimmick. It’s a fundamental psychological principle: A great intro—like an electrifying opening to a film—buys goodwill with readers. Buy enough goodwill and readers look past the weaker parts of your post—because they're chasing the high from your great opening.

And, most intriguingly, the flipside of a hook is a novel idea you can write about. Let me show you what I mean.

What is a hook?

A hook is a half -told story. You raise a question then tease only part of the answer:

  • Questions — Pose an intriguing question, but don’t give the full answer.
  • Narratives — Share the start of a narrative, but withhold the conclusion.
  • Research — Highlight research findings, but only a small portion.
  • Arguments — Make an unexpected claim, but don't explain how it's true.

Hooks serve two purposes:

  • They compel readers to continue reading. They switch on the storytelling machinery in readers' heads.
  • They help you identify what's interesting—novel—to write about.

We don't need the answers to our hooks—yet. At this point, we're just trying to find the most interesting questions we can possibly pose that will get people to keep reading. Later, our hunt for answers will become our pursuit of novelty.

Let's look at four types of hooks.

1. Narrative hooks

With a narrative hook, you share the beginning of a profound change in circumstances, but you withhold the conclusion.

Provide just enough details for readers to feel emotionally invested.

My clothes turned to ice. I took them off and looked for a fresh pair—before realizing that I hadn't actually brought one.

The pair I just removed took off with the wind and over the mountainside.

I was now standing—bare—on an arctic summit. I had no way of avoiding full-body frostbite and death by hypothermia.

It was 3 AM and there wasn't a soul within miles.

That was the day I lost everything. And this is the story of what happened next.

2. Research hooks

With a research hook, you highlight fascinating findings—but only a portion.

I tracked all 90 living individuals who were born without the ability to sense pain.

80 of them are living normal lives by following strict day-to-day regimens.

The remaining 10, however, are defying everything we know about what it means to survive. They've led to the discovery of fascinating new drugs.

3. Argument hooks

With an argument hook, present a bold claim but withhold how you arrived at it.

There's a 90% chance that Cloudtex goes bankrupt within thirty days. This post walks you through the startling corruption that triggered their downfall.
There's a reliable technique for getting yourself to sit down and write—to completely break through procrastination every single time.

Asking a question isn't enough

For a hook to resonate, readers must be given enough context to care about the rest of the story.

Therefore, our intro must accomplish two things:

  • Give readers a reason to care about our hook. Connect it to meaningful problems they face. (Failing to do this is where most intros go wrong.)
  • Hook readers with half of an interesting story.

Hooks become talking points

When you identify a good hook, you've also identified a compelling idea to explore in the rest of your post.

And that's the point: great hooks force you to write something novel.

If you can't find good hooks on your own, ask others what questions they most want answered on your topic. Find the answers then turn those into hooks.

Note that there are many ways to write. I'm sharing approaches that I find most reliable. There is no right or wrong way—only what works best for you .

Are you bored right now?

If you don't care to learn about the ideation process, you can skip half this guide and continue at Page III (Rewriting) for rapid fire advice on improving your writing.

.

While a hook pulls readers in, skepticism is what pushes them away.

Skepticism often outweighs the strength of your hooks, causing readers to abandon your writing. But, you can do something about this.

In your intro, consider proactively countering any major skepticisms that exist. There are five types of skepticism to counter:

  • Superficial : Superficial skepticism emerges from readers not believing you’ll share things they don’t already know. Solution : Tease your original insights in your introduction.
  • Irrelevant : Readers don’t believe you’ll cover key points they care about. Solution : List the points you’ll cover.
  • Sloppy : Readers don’t want to sit through bad writing. Solution : Rewrite your intro to be clear, succinct, and intriguing.
  • Implausible : Readers don’t believe you’ll deliver on your hooks. Solution : Include quotes from authorities who agree with you.
  • Untrustworthy : Readers don’t believe you're qualified to write about this. Solution : If you have relevant credentials, share them. If not, make your hooks so captivating that they can't help but continue reading. Make the rest of your post so insightful, logical, and well-researched that they believe you. Or, if you're indeed unqualified, be upfront about it and frame the post as an exploratory journey you're taking them on.

If you successfully hook readers while neutralizing their skepticism, you generate goodwill: now they're invested in reading the rest of your post.

Example of combatting skepticism

Below is the introduction to my Build Muscle handbook. I've indicated the passages used to address skepticism.

Intro

This handbook is the result of a year's research into what the latest science shows is the most efficient way to build muscle. ↑ Address the Untrustworthy objection: reassure readers you have the requisite wisdom to be authoratitive.

It's for both men and women. It's primarily for beginners, but there's plenty of science-backed advice for intermediates too.

I wrote this guide because much of the casual weightlifting advice is unsubstantiated or misleading. I can't blame bloggers for it, because some of the facts in this guide have not been broadly published outside of the scientific literature.

As a result, this handbook contradicts some popular bodybuilding recommendations, including the myth that women have a harder time gaining beginner muscle, that exercise rest times should be kept to 1–3 minutes, that most body weight exercises are useful, that machine exercises are ineffective, and so on.

Throughout this handbook, I support my claims by citing studies and showing you how to measure your weekly gains so you can confirm you're growing.

Speaking of growth, if you're starting without muscle, you can grow it fast if you're diligent about eating, exercising, and sleeping. You can gain up to 12-15lbs (6.8kg) of muscle in 3 months when closely following a researched program such as this. (Afterward, muscle gains slow drastically.) ↑ Address the Superficial objection: reassure readers you’ll share new knowledge they don’t already have.

In addition to thoroughly citing research, this guide is also comprehensive. I dislike tutorials that provide 75% of what you need to know then leave you with questions.

We'll learn what the research says about:

  • How to eat to gain muscle mass.
  • The most effective exercise routines.
  • Measuring your weekly muscle gains.
  • Overcoming plateaus.

Address the Irrelevant objection: reassure readers you’ll cover topics they care about.

Inspired? Good. If you weren't willing to spend 1–2 years in the gym to get results before now, be excited because you can compress beginner gains into 4 months.

Oh, and I have nothing to sell you. This handbook is free. There's no promotion. ↑ Address the Implausible objection: reassure readers you can deliver on your claims. In this case, I use the truth that I'm not trying to sell them anything.

Learn how to write an introduction paragraph. This guide explains the writing process for introductions, as well as the process for deciding what to write about.

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How to write a first draft

The goal

An artist with one great work likely doesn’t know what makes it good. If they did, they'd have more great works. So, in their case, I just appreciate the work itself.

But an artist with a streak of masterpieces, such as Christopher Nolan, is indeed a master. In that case, I try to reverse engineer their process. They clearly have one.

I believe I've engineered a writing process for blog writing too.

Our process

I write the worst first draft I can as quickly as I can. Because almost all the work happens during rewriting anyway. The greatest friction is in putting ideas down in the first place.

That means, in my bad first draft, I use placeholders any time I'm stuck: when an idea requires more thought than I want to put in, I write <to fill out> and move on.

Your first draft is like speedrunning. The goal is just to generate and connect ideas. Not to explain everything, and certainly not to say things well. Save that for rewriting.

To repeat, your first draft is simply for generating and connecting ideas :

  • Brainstorm talking points.
  • Connect those points together to learn what you’re really trying to say.

This works best when you’re exploring ideas that most interest you . The more self-indulgent you are, the better your article . More on this shortly.

When you write a first draft, you write it for yourself. When you rewrite it, you write it for everyone else.
—Stephen King
Rewriting .

:

  1. Example .
  2. Example .
  3. Example .
  4. Example .
  • Supporting points
  • Resulting points
  • Objective
  • Supporting points
  • Resulting points
  • Objective
  • Supporting points
  • Resulting points

2. Outline your talking points

Supporting points typically come first and resulting points typically come last. But, there is no correct outline. Hundreds of paths lead to your objective. Say as little or as much as you want.

The only requirement is that you focus on points that are novel. Content is driven by novelty.

Here’s an example outline for the objective of Challenging the status quo :

  1. State that the reader’s current view of the world is false. Supporting point
  2. Establish how so many people being wrong about this hurts our world. Supporting point
  3. Establish what’s required to get everyone to change their view. Supporting point
  4. Predict how the world would be different once the transition is complete. Resulting point
  5. Explore the exciting byproducts of the world being different. Resulting point

Fill in the gaps

Take a moment to examine your outline. What’s still needed to convincingly and logically tie your points together?

In the outline above, I found two gaps worth plugging:

  1. State that the reader’s current view of the world is false. Supporting point
  2. Provide supporting evidence for your claim. New supporting point
  3. Establish how so many people being wrong about this hurts our world. Supporting point
  4. Establish what’s required to get everyone to change their view. Supporting point
  5. Predict what a transitionary period would look like. New resulting point
  6. Predict how the world would be different once the transition is complete. Resulting point
  7. Explore the exciting byproducts of the world being different. Resulting point

More objective outlines +

  • Supporting point
  • Supporting point
  • Resulting point
  • Resulting point
  • Supporting point
  • Supporting point
  • Resulting point
  • Resulting point
  • Supporting point
  • Resulting point
  • Supporting point
  • Supporting point
  • Supporting point
  • Resulting point
  • Supporting point
  • Supporting point
  • Supporting point
  • Resulting point
  • Resulting point
  • Supporting point
  • Supporting point
  • Resulting point
  • Resulting point

3. Write your initial thoughts

Under each talking point in your outline, start by writing half-formed thoughts.

It’s more efficient to breeze through a bad first draft and improve it later than to try starting from perfection.

Your ideas will come from a few places:

  • Hooks — Answer the captivating questions raised in your intro.
  • Experience — Reflect on observations and anecdotes.
  • Research — Acquire knowledge.
  • Experiments — Run tests.
  • Brainstorming — Voice-record then transcribe your thoughts.
  • Mental models — Think critically.

It’s normal if not many ideas come to mind immediately. You’ll discover that the majority of your ideas arrive while writing—not before. You write in order to think.

You'll discover the rest of your ideas by resting and reflecting on what you’ve written. The act of writing compels your brain to draw connections between ideas.

It can’t help itself.

People think you need to be inspired to write. No, you write in order to get inspired.
—Paul Jarvis

Which of my ideas are good?

How do you know which thoughts are most valuable? What separates good from bad ideas?

The solution is to focus on ideas that are interesting or surprising . These are the ingredients of novelty. Novelty is what keeps readers reading. They tend to be:

  • Counter-intuitive
  • Counter-narrative
  • Shock and awe
  • Elegant articulations

Interesting talking points

To uncover interesting ideas, continuously make your next point whatever interests you most. Skip everything that bores you.

When something bores you, it probably bores your readers too. And if something entertains you, it probably entertains them too. You're a proxy for your die-hard readers.

That’s the irony of self-indulgent writing: writing for yourself is the quickest path to writing something others love.

The mistake writers make is believing expertise is required to write nonfiction. Nope, it's the rabid desire to indulge your curiosity.

Your voice

Something wonderful happens when you focus on what interests and surprises you : your voice emerges.

Readers begin to notice:

  • What you care about.
  • The perspectives you see the world through.

Readers love this. It makes your writing feel personal.

I just write what I want. I write what amuses me. It’s totally for myself. I never in my wildest dreams expected this popularity.
—J.K. Rowling

Surprising talking points

In addition to interesting talking points, you're also looking for surprising ideas.

Surprise is anything that contradicts what readers know or expect you to say. It makes them think, “Wow. That’s unexpected.”

You generate surprising talking points using Paul Graham’s Method: First, learn the basic knowledge of a topic. Then, if you can find new information that surprises your knowledgeable self, it’ll surprise laypeople too. You can also play detective: when you know enough about a topic to know what's not known about it, you can selectively resolve those gaps and share the discoveries.

Again, you are your audience's proxy. There's no need to guess what will surprise them. Hunt for something that surprises you, and others will be along for the ride.

When you get stuck

When ideas stop flowing, ask yourself:

  1. How can I make this point more convincing?
  2. What are the interesting implications of what I just said?

Repeatedly ask these two questions and keep moving in whichever direction interests you most.

Your outline should be specific enough to provide structure, but loose enough to not confine expansive thinking. Whenever you feel a tug pulling you away from your outline, indulge that curiosity. Pursue that adventure.

You can prune the bad stuff later.

Refer to my blog post on how to generate good ideas: Creativity Faucet .
I hated English in high school. But if they called it Thinking, then I wouldn't be as terrible of a writer as I am today.
—Quoc-Anh Vu

while

You write in order to think.

Learn how to write a good first draft. This guide explains the process for generating writing ideas, exploring their potential, and practicing the writing process.

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How to rewrite your first draft

Rewriting

Your favorite authors’ first drafts are typically bad. However, what elevates great authors is their discipline to aggressively rewrite their first drafts in pursuit of:

  1. Persuasive reasoning
  2. Being clearly understood
  3. Sustaining curiosity
  4. Resonance — Story, analogy, and poetry

The enemy of those objectives is being precious about what you originally said and how you originally said it.

When you first write an idea down, you do so in whatever disjointed way immediately came to mind. Rewriting is the art of finding puzzle pieces within that mess and putting them together in the right order.

In short, your first draft is to extract novel ideas out of your brain. Your second draft is to rewrite those ideas so they resonate.

When rewriting, consider listening to atmospheric music. It helps reduce your susceptibility to distraction: a steady beat without vocals helps put you in a trance. Here's my Spotify playlist .
The process of writing your second draft is the process of making it look like you knew what you were doing all along.
—Neil Gaiman

1. Being understood

Readers don't assess the quality of nonfiction writing by its elegance nor its complexity. Instead, they assess:

How strong the ideas are x how intuitively they understand them

You get in the way of that understanding by making your writing unclear.

What is clarity?

Clear writing starts with clear thinking:

  1. What am I really saying?
  2. What is the point I must make here?
  3. How can I make this point easy to understand?

We'll explore two tools for accomplishing this:

  • Simple sentences
  • Examples and counterexamples
Anything that can be said can be said clearly.
—Ludwig Wittgenstein

Simple sentences

Write sentences that a thirteen-year-old could follow.

If they can understand, so can everyone else—including anyone who's skimming.

This isn't to say children should understand the details. Rather, children must be able to follow the logic of your arguments.

You already do this intuitively. When speaking to children, you simplify:

  • You use plain phrasing.
  • You use fewer ideas per sentence.

We're going to use these techniques in our writing too.

Remove abstract phrasing

Here's a sentence with complex phrasing:

"The obstacle facing media organizations is to chart an economically sustainable course through a landscape of commodity journalism.”

Let’s rewrite that sentence plainly:

“News companies are having a hard time staying in business because anyone with a blog or Twitter account can report the news now."

That's how you talk to a thirteen-year-old. In fact, that's how you should talk to everyone all the time.

In the revised example, I removed abstract words like "charted" and "landscape," and I reduced a conceptual idea into a specific example.

By removing this overhead, the underlying point stands out. That's our goal.

Grammatical simplification such as this doesn't make your writing worse. The complexity of your writing should emerge from the strength of its ideas, not from how those ideas are worded.

However, don't drop key information when simplifying. This, for example, would be too reductive:

"News companies are not doing well today."

That loses the point of why news companies are not doing well. Simplify your sentences without removing the nuances.

One last example. Let's remove abstract words and talk plainly:

Bad paragraph — "Ignorance of corporate dynamics represent a persistent source of pain for a certain type of operator. Intelligent but inexperienced. I’d recommend that you avoid this pain by understanding how other people make decisions in the context that they’re incentivized to do so and by appreciating the constraints they’re operating within."
Rewritten — "It’s common to be a smart person who’s unaware of what’s going on. I recommend writing down the frameworks your team uses to make big decisions. Then, when a colleague proposes an idea that doesn’t intuitively make sense to you, think through their idea using their own frameworks. Work from there to build empathy and have a constructive dialogue."

Use fewer ideas per sentence.

The second simplification technique for talking to children is using fewer ideas per sentence.

Consider this bad paragraph:

“There's a fast growing collection of data describing the structure and functional capacity of human gut bacteria in a variety of conditions. Ongoing efforts to further characterize the multitude of functions of gut bacteria and the mechanisms underlying its interactions will provide a better understanding of the role of the microbiome in human health and disease.”

Let’s rewrite that for a thirteen-year-old:

“There’s plenty of research on gut bacteria. We’re quickly learning which roles gut bacteria play and how they interact with each other. Researchers want to better understand how these bacteria can affect our overall health.”

The original paragraph's sentences contained two ideas each. That’s a problem. Your brain interprets the meaning of a sentence after it's done reading it. So, the longer the sentence, the more details you hold in your head at once. That makes understanding already complex points even harder.

Don't be mean to your readers. Make it effortless to digest your thoughts.

Recap

It’s okay to make readers work to uncover the implications of what you’re saying. But, it’s not okay for them to struggle to understand what you're saying in the first place.

When you keep your language simple, you can get away with making your ideas infinitely complex.

Provide examples

Examples are another tool for improving readers' understanding.

Examples convey the significance of an idea by relating it to real-world situations. They also help readers learn concepts in the context of what they're familiar with, which aids in recall. Examples are what make abstract ideas specific .

Tips for providing examples:

  1. Provide more than just examples of a job well done. Also provide before-and-after examples and counterexamples to clarify what you mean and don’t mean. Help readers orient themselves on a spectrum of right to wrong.
  2. If you make your examples fun and topical, readers pay more attention.
  3. Examples with many moving parts should be turned into diagrams.
  4. Don't waste time with examples if you're confident your point was self-evident.

Clarity benefits the writer

After you've rewritten your draft for clarity, you’re left with a better understanding of what you're trying to say. Then you can focus on saying it more persuasively.

Recap

  • Simple language doesn't weaken your writing. It strengthens your points by helping your underlying ideas stand out.
  • If you imagine you're writing for an audience of thirteen-year-olds, you'll deliberately think and write more clearly.
  • Use plain wording, simple sentences, and before-and-after examples.
I don't actually know the rules of grammar. If you're trying to persuade people to do something, though, it seems to me you should use their language.
—David Ogilvy

2. Sustaining curiosity — Succinctness

After clarity, the next step in rewriting is succinctness : remove everything you now realize is not required to make your point. This is how you get readers to finish your post. Most readers quit not because they dislike your ideas, but because they're bored.

Succinctness is a ratio: it’s the number of significant ideas to total word count. A post can be 50,000 words, but if it's still dense with insights and devoid of rambling, it's succinct.

Be deliberate

Beginning writers treat writing as a clearing of their consciousness. They write every thought that comes to mind—one sentence after another—until they’ve hit whatever word count they believe they’re supposed to hit.

In speech, when you say something that doesn't resonate, you can add sentences to further explain your point. Don't do that in writing. If your sentence doesn’t resonate, you go back and rewrite it.

Writing is a process of deliberate thought curation—where each sentence justifies its existence in your final draft.

I once stumbled into a silly book review that helps make my point:

"Great book, but overpriced. $15 for a 100-page book?"

Actually, your $15 got you 100 pages plus three hours of your time back. A 100 page book excludes 200 pages of filler. The author did you a favor. They understood that while words are free for them, they're costly for the reader.

When a deliberate writer has written something down, they then ask:

  • What is the purpose of the statement I just made? What effect does it have on the reader’s mind?
  • Is there something more useful I could have said here instead?

Later, when they get stuck trying to explore their ideas, they ask:

  • How can I make this point more convincing?
  • What are the interesting implications of what I just said?

How to rewrite for succinctness

Here is my three step process for being succinct.

1. Step 1: Rewrite entire sections

For each section of an article, I will:

  1. Read it.
  2. Take an hour-long break.
  3. Rewrite the section from memory—focusing only on the critical points.

The new version written from memory will take a more direct path toward what's important. The fluff falls away when you focus on effectively re-articulating yourself.

An alternative approach is to call a friend: Have them read your draft then summarize it over the phone in thirty seconds. Delete your draft and restart from their summary. Add more words only as needed to make your ideas resonate.

I call these verbal summaries, and they're a key to succinctness.

Example: Verbal summary +

Original, non-succinct intro

I thought I was on the fast-track, but I was wrong. After joining one of the fastest-growing startups in history, I was putting in 80+ hour weeks, reading every career book I could get my hands on, meeting with high-powered department heads—and it all led nowhere.

At 25, I was miserable, lacked career fulfillment, and started believing tech was overhyped. Work felt hollow. There were no clear next steps and all I faced from my manager was canned feedback about focusing on the task at hand.

Only later did I realize that my misstep was obvious. I was following the wrong recipe; the conventional career ladder would not move at the pace I demanded.

My major breakthrough was ignoring personal growth to optimize for a company’s growth. And my current role at a large organization didn’t allow me to visibly move the needle. After joining a younger, less-defined company, there were a million ways to add tangible value. I tried to exhaust all of them until I found the right ways to solve problems at scale.

Performance reviews became far less important than constantly delivering results. Having outsized impact unlocked new levels of personal growth. Following the conventional wisdom to round out skills or check boxes for a promotion would have taken longer and been less rewarding.

This different approach also led me to think outside of a specific ‘ladder.’ I carved my own path—one that led to creating my own high-impact roles.

I want to help you avoid my mistakes and create a rewarding career. While everyone else is climbing a defined career ladder, build your own. It’s more fun.

New intro after verbal summary

Incentives between employees and companies are misaligned.

To fast-track your career and find genuine fulfillment in your work, you must bend your job responsibilities to your will: identify the overlap between personal growth and the opportunities that create an outsized impact at your company. Then argue for your right to exist at the intersection. Prove it to your managers.

You need to carve your own journey instead of blindly climbing the corporate ladder—or you're a cog in a machine.

And here’s the trick: The smaller the organization, the more possible this becomes.

↑ Above, we condensed the original intro using a verbal summary. The next step is to slightly re-expand it by adding color and story to make its points resonate.

To be brief on the sentence-level, you should remove filler words that don’t add necessary context to the sentence . This isn't intuitive to novice writers: extra words cause readers to unwittingly slow down and do extra work while reading . That makes it harder for them to recognize the sentence’s true point. Reading many extra words is also a chore for your brain. And when you exhaust readers, they quit reading.

That leaves us with:

To be brief on the sentence-level, remove words that don’t add necessary context. Extra words cause readers to slow down and do extra work. That makes it harder for them to recognize the sentence’s point. And when you exhaust readers, they quit reading.

With unnecessary details removed, it becomes clear what's most valuable to say.

3. Step 3: Rephrase paragraphs from scratch

Now that we know what we most want to say, we're in a position to succinctly rephrase each paragraph.

Again, here’s our paragraph:

To be brief on the sentence-level, remove words that don’t add necessary context. Extra words cause readers to slow down and do extra work. That makes it harder for them to recognize the sentence’s point. And when you bore readers, they quit reading.

Let's rephrase that from scratch:

Your sentence is brief when no additional words can be removed. Being succinct is important because filler buries your talking points and bores readers into quitting.

Bingo. That's succinct. No one is getting bored midway through that paragraph.

Repeat the (1) word removal and (2) rephrasing from scratch process for every paragraph. When you’re done, your article will be a third as long and less boring.

The Tweet test

After writing a post, I try compressing it into a single tweet. If I can pull that off without losing anything important, I delete the post and publish the tweet instead.

But if I have to split the post over multiple tweets, I know I have something meaty, and so I publish the post.

"If it is a ten minute speech, it takes me all of two weeks to prepare it. If it is a half-hour speech, it takes me a week. If I can talk as long as I want to, it requires no preparation at all. I am ready now."
—The Operative Miller

Try this yourself

Make this paragraph succinct:

"Q System One was a quantum computer. The machine was the culmination of a year—or decades, depending on how one measures—of labor and ingenuity from IBM scientists. The researchers had assembled this stalactite of nested canisters in the recesses of the company’s neo-futuristic research center in Yorktown Heights, N.Y. The white, refrigerated contraption dangled from a nine-foot, cubic, aluminum and steel frame. In the innermost chamber: a special processor whose progeny could help solve some of the world’s most intractable science and business problems. This particular generation featured the firepower of 20 quantum bits, or 'qubits,' the powerful data units upon which these dream machines operate."

First, remove unnecessary words. With the clarity of what remains, rephrase it succinctly.

3. Sustaining curiosity — Intrigue

Clarity and succinctness are what help ideas resonate. They reduce the friction of reading. But it’s intrigue that gets people reading in the first place.

Intrigue is generated in two ways:

  • Saying something novel — A novel claim is one that's counter-intuitive, counter-narrative, surprising, or elegantly poetic. It isn't something readers would have easily intuited on their own, and it's related to something they care about.
  • Withholding information — Tease readers with a question you don't answer until later.

If these recur throughout your post, readers are likely to remain engaged.

Place gold coins along the path.
—Roy Peter Clark

1. Novelty

I use a technique I call dopamine counting to weave novelty into my writing:

  • I ask people to leave feedback by highlighting every sentence that gives them a dopamine hit. These are the moments of novelty where they remark: "Ahh, that's interesting." For each hit, I increase a counter at the end of the corresponding sentence. Like this (3).
  • After several people have left feedback, I look for long stretches without dopamine hits. Then I rewrite those sections to be more concise—or I inject more novelty (insights and surprises) into them.
  • I rinse and repeat until the article has a steady cadence of dopamine hits.

If you've read this far, dopamine counting is what got you here.

Example of dopamine counting +

Below is my Creativity Faucet essay from earlier in this guide. I shared this with friends and asked them to indicate which parts gave them dopamine hits.

The most valuable writing skill is generating a high frequency of novel ideas.

Last year, I stumbled into a mental model to achieve this.

I was watching a documentary on songwriter Ed Sheeran. In it, he described his songwriting process. It struck me as identical to the process that author Neil Gaiman detailed in his Masterclass.

Here's the thing.

Ed Sheeran and Neil Gaiman are in the top 0.000001% of their fields. They're among, say, 25 people in the world who consistently generate blockbuster after blockbuster.

If two world-class creators share the exact same creative process, I lean in. (4)

I call their approach the Creativity Faucet:

Visualize your creativity as a backed-up pipe of water. The first mile of piping is packed with wastewater. This wastewater must be emptied before the clear water arrives.

Because your pipe only has one faucet, there's no shortcut to achieving clarity other than first emptying the wastewater.

Let's apply this to creativity: At the beginning of a writing session, you must write out every bad idea that reflexively comes to mind. Instead of being self-critical and resisting these bad ideas, you must openly accept them.

Once the bad ideas are emptied, strong ideas begin to arrive.

Here's why: Once you've generated enough bad output, your brain starts to reflexively identify which elements cause the badness. Then it begins to avoid them. You start pattern-matching novel ideas with greater intuition. (9)

Most creators never get past their wastewater. They resist their bad ideas. (8)

If you've opened a blank document, scribbled a few thoughts, then walked away because you weren't struck with gold, then you too didn't get past it.

Neil and Ed know they're not superhuman. They simply respect the reality of human creativity: The brain has a linear pipeline for creativity, and the pipe needs clearing. In every creative session, they allot time for emptying the wastewater.

They're not worrying whether clear water will eventually come. It always does: (7)

  • Your work start as a weak imitation.
  • You identify what makes the imitation weak.
  • You iterate on the imitation until it's original. (5)

2. Withholding information

The second technique for sustaining intrigue is withholding information.

Storytelling in general is actually the art of choosing what to withhold. When rewriting, decide which answers you want to reserve until the end.

The psychology of intrigue

Recall from earlier the psychological principle for introductions:

The hook principle — "A captivating intro buys goodwill with readers so they overlook an imperfect middle."

Let's pair that principle with a second:

The peak-end rule — “People judge an experience largely based on how they felt at its most intense point and at its end. This implies they do not judge the experience based on the average of every moment.”

Together, these two principles help us guarantee readers enjoy our writing:

  1. Have a captivating intro that buys goodwill.
  2. Have at least one peak of insight or surprise.
  3. Have an ending that satisfyingly justifies why the piece was worth reading.

There’s your writing formula. The rest of your article can be weak and most readers will still enjoy it. Take comfort in the implication: not every paragraph has to be interesting.

Let's apply the peak-end rule to cinema: Many boring indie films are held together by one intensely poetic scene and a cathartic ending. That’s all they need for people to enjoy them.

We already learned intrigue

On the previous page , I shared my process for generating insight and surprise: use yourself as a proxy for the reader then lean into what excites you .

Next, to craft your article’s peak, simply condense your most insightful and surprising talking points into one section. Build that climax.

The previous page also discussed how to make your ending satisfying: poignantly summarize how your ideas are relevant to the reader’s future.

Takeaways

  • 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.
  • In long pieces, aim to evenly distribute dopamine hits. Rely on outside feedback; it's hard to accurately judge this yourself.

Where you are

Let's resituate you in this handbook:

  1. Choose a topic
  2. Write your intro, and use it to brainstorm talking points
  3. Get feedback on your intro
  4. Create an outline using your objective
  5. Explore talking points within your outline
  6. Rewrite for clarity, succinctness, and intrigue
  7. Cycle between rewriting, resting, and receiving feedback ← You're here
  8. Copy edit for grammar, word choice, and style

Feedback

Feedback is the only efficient way to improve your writing. This is not optional.

Giving feedback is also the most efficient way to hone your eye for rewriting: leaving it for others forces you to internalize the learnings in this handbook.

Asking for feedback

Ask for feedback from the audience you’re writing for. Here’s a template:

It would be helpful if you read my article slowly to transcribe the reactions you have while reading it. For example:

1. Tell me what to delete — When you notice your interest is fading, you can say “I'm drifting here. This isn’t compelling and it isn’t adding value. Get to the point quicker and hook me."

2. Tell me what to double down on — When something excites you, you can say “Dopamine hit. Go further in this direction. I have more questions.”

3. Tell me what isn't clear — When you're done reading, please score this from 1-10 on how satisfying it was. Don’t be afraid to give me a low score. By telling me this needs work, you're sparing me from releasing bad work to the public.

Keep asking for feedback then rewriting until you average a score of 7.5+ across a handful of respondents. That puts you in the "this was a good read" category.

Do not waste time striving for 9+. One reader's 9 is not the same as another's, so trying to satisfy everyone results in a bloated post that satisfies no one. There are many great ways to tell a story, so be happy when you’ve found one that works.

Thanks to Brian Tait, Matthew Mueller, Nat Eliason, Lachy Groom, and Andrew Askins for giving me feedback on this handbook.

Feedback from your future self

Your best source of feedback is often you with the benefit of hindsight. But you need a break to get that perspective. I’ve found a week is often enough time to sufficiently defamiliarize myself.

If I personally have a writing superpower, it's that I can look back at my work with a hyper-critical eye—and I can do this repeatedly. And I enjoy it.

Take it from the world's most successful hyper-prolific writer, Stephen King: he shoves his manuscript into a drawer for six weeks before writing his final draft. When he re-opens it, he sees its flaws with fresh eyes.

I've also found that switching writing tools tricks my brain into re-reading my work with new eyes. For example, if I wrote the first draft in Dropbox Paper, I'll write the second draft in Google Docs. Those tools format text differently, which kicks your brain out of pattern recognition mode, and makes it feel like you're editing someone else's work.

These are the writing problems I can only identify with the benefit of a break:

  • Awkward sentences.
  • Not being persuasive.
  • Not sustaining intrigue.
  • Not being succinct on a section-by-section level.

However, I can catch these in real-time:

  • Typos.
  • Unclear sentences.
  • Not being concise.

Incorporating feedback +

  • you

Plagiarism disclaimer

I've noticed bloggers and course creators repurposing my work and passing it off as their own. Please be thoughtful about plagiarism. I keep a third-party timestamp of my handbooks, and I can see the history of changes on your site by using Archive.org . Together, they identify when someone has taken my work.

Learn to rewrite your articles for clarity, succinctness, intrigue, and style.

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How to write with style

Style engages the senses

Style is also summoning images into a reader's mind.

One way to do this is via vividness. To explain vividness, here are writer Venkatesh Rao's remarks on the vividness of author David Foster Wallace:

"When I read a Wallace passage, it's like looking at a pinprick-sharp photograph—compared to my own blurry photographs. He unerringly picks words to use that simply work 100x better than my choices. It's like he has a 15 megapixel camera and a tripod, while I am using a three megapixel point-and-shoot. A bigger vocabulary isn't enough. The skill lies in matching words to needs."

Here's an example of vividness:

One of my favorite moments of the year involved a beetle doing yoga on a desert dune. In the Namib desert in Africa, the darkling beetle's day begins with an ascent of a massive sand dune. A tiny creature faced with a Himalaya-sized trek. Undeterred, it marches on, its legs as skinny as a runner's, up towards the summit above which a fog from the Atlantic hovers.

When it gets there, the beetle inverts its body into a headstand and stands very still. Then magic occurs. No, wait, it is something more fantastic than magic, it is nature. This is a planet about to do some of its very best work.

Droplets of water form on its shell as the fog condenses on its body. Then slowly, using grooves in the beetle's casing, the water rolls into its thirsty mouth. This is how life is sustained on earth.

—Rohit Brijnath

It's akin to cranking the saturation dial in Photoshop.

Notice how vividness isn't just detail. It's detail that resonates. It's the articulation of the rarely articulated nuances of life—in a way that makes you remark, "Ahh, that’s how I'd put words to that feeling."

Word choice

To engage a reader's senses, you can do more than just add vivid details. You can also swap plain words for engaging ones.

Watch how I switch words out here:

“Here is my story of breaking into Hollywood.”
→ “Here is my tale of breaking into Hollywood.”
“After college, I traveled to India.”
→ “After college, I journeyed to India.”

I'm now using words with greater specificity or emotional weight.

We can push further. We can extend beyond literal language to use figurative. Pay attention to the bold words, which now create metaphors:

  • “Make me an instrument of your pain.”
  • “Where there is hatred, let me sew love.”
  • “It is the mark of an educated mind to be able entertain a thought without accepting it.”
  • “Blessed are the hearts that can bend ; they shall never be broken.”

Those are all famous quotes. What makes them beautiful is their use of metaphorical synonyms in place of plain words. Specifically, they're using words that are uncommonly used in these contexts but whose meaning is nonetheless clear. To do this yourself, use a thesaurus to hunt for great word pairings.

A common technique for applying metaphor is to ascribe human qualities to inanimate things. This gives inaminate things dimensionality:

  1. Angry storms
  2. Shrieking sirens
  3. Dancing leaves
  4. Coy flames
  5. Tired gears

This gets us back to the goal of evoking a reader's senses. One study showed that brain scan participants who read the words "He had a rough day" activated neural regions associated with feeling texture, whereas those who read "He had a bad day" didn't trigger the same effect.

As soon as you have found the words with which to express something, you are no longer incoherent, you are no longer trapped by your own emotions, by your own experiences; you can describe them, you can tell them, you can bring them out of yourself and give them to somebody else. That is an enormously liberating experience.
—Jeanette Winterson

Style engages the imagination

Style engages the imagination. When it does so elegantly, we call this poetry.

I define poetry as finding evocative, unconventional ways to say meaningful things.

For example, instead of saying "the day was hot," you could write “even the bugs were looking for air conditioning.”

In that example, we're describing the effect caused by our subject (the hot day)—as opposed to directly describing the heat itself. In other words, poetry is one step removed from a straightforward description of the events.

The more steps you can be removed while still successfully communicating the meaning, the more "elegant" your poetry feels. The more profound your underlying point, the more "deep" your poetry feels.

Let's walk through an example using a framework I devised.

First-order description

In a first-order description, you directly describe how something is.

The day was hot.

This is how we commonly talk.

Second-order description

In a second-order description, you describe something by stating an effect it has on its environment.

The day melted our popsicles.

The reader can imply that the day was therefore hot.

Third-order description

In a third-order description, you describe something by stating its effect but not mentioning the cause by name.

Our popsicles melted.

Above, there's ambiguity as to why our popsicles melted. But with a bit of imagination , the reader pieces it together.

However, our sentence isn't very poetic yet. To get there, we choose an effect that is unconventional, counterintuitive, or witty:

Even the bugs were looking for air conditioning.

This style of writing evokes mental imagery and world-building. That's a more evocative and original way to set a scene than writing "the day was hot."

In short, I personally define poetry as unconventional third-order descriptions.

Instead of telling us a thing was "terrible," describe it so that we’ll be terrified. —C.S. Lewis

Style is presentation

There are infinite ways to tell your story. How you tell it is a matter of presentation :

  • Wait But Why uses cartoon drawings and analogies to explain complex topics.
  • Maddox uses dark humor , crude GIFs , and videos to shock and entertain.

Would analogies, anecdotes, humor, or multimedia help better convey your ideas? If so, consider using them. You want your ideas to resonate.

Takeaways

  • An authentic voice resonates best with readers: your way of speaking, your interests, and your perspectives on the world are a breath of fresh air when unfiltered. Write nonfiction the way you sound.
  • Consider metaphorical explanations that are a couple degrees removed from a literal telling of the events. Engage readers' imaginations and paint vivid landscapes.
  • Optionally incorporate multimedia, anecdotes, analogies, and humor to reinforce your points and to entertain.

Learn to convey your voice, copy edit, and add color to your writing.

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How to practice writing

Key learnings from this guide

  • Your goal isn't to build a writing habit. Your goal is to fall so in love with interesting ideas that you can’t not write about them. Find your objective and your motivation.
  • Don't wait for an idea to be fully formed before writing. You write in order to think through the idea. The act of writing compels your brain to connect the dots.
  • Avoid guessing what readers want. Instead, be a proxy: Selfishly entertain and surprise yourself, and you'll entertain and surprise many of them too.
  • Your writing is clear once your thoughts are self-evident.
  • Your writing is succinct once everything unimportant is removed.
  • Your writing is intriguing once the average reader effortlessly makes it to the end. A hook, peak, and satisfying ending are your trifecta of intrigue.
  • Rewriting your thoughts to be clear, succinct, and intriguing is a lot of work. You won't love writing until you find a way to love rewriting. Make a game out of it.
  • There is no right way to write—just like there’s no right way to paint. In this handbook, I present frameworks that reliably work for me. Ultimately, you can break every single rule if your writing is still interesting.

All of these takeaways, and more, are recapped in a cheat sheet at the bottom of this page.

Building the writing habit

I became a writer when two things were true:

  1. I had strong opinions to express and nagging questions to answer.
  2. I could build the discipline to fully reason through my ideas.

And I'm ready to write a given post once I've reached two thresholds:

  • I can't shake the idea. It won't stop nagging me.
  • I've uncovered at least one novel insight about it. (I'll unravel more through the process of writing and rewriting.)

Even if you reach these thresholds, sometimes you'll encounter existential blockers. Let's tackle them.

1. Blocker: Lacking good ideas

Four shortcuts for sourcing topics to write about:

  • Trigger ideas that bug you — Your strongest opinions make for the best writing. To trigger opinions, consume other people's views (via Twitter, news, and conversations) and make a note whenever you strongly disagree. Then crack open a laptop and argue your counter-position on paper.
  • Capture real stories you tell — Readers love being privy to authentic stories from a writer's life. Write down a vulnerable story you'd tell a close friend. Intersperse cliffhangers throughout.
  • Be a diligent note-taker — Save every idea you come across that's interesting or surprising. After a few months, you'll have a backlog of intriguing ideas to mold into something worthwhile. This is how I write.
  • Explain concepts to others — Put yourself in a position to synthesize your life experience for others. Teach. Mentor colleagues or call friends to explain the ideas you're working through. While explaining, pay attention to how you explain key concepts: occasionally, you'll articulate the essence of a concept beautifully—and that articulation will make for a great piece of writing.

2. Blocker: Concerned no one will read

Write in order to make sense of your mind and the world around you. Accept that most of writing's value comes from helping you clarify your own logic. The resulting clarity makes you a wiser speaker and decision-maker.

When clarity is your goal, having an audience matters less. For a writer to have a long career, I find it's critical to approach writing this way.

Fortunately, getting to the bottom of the ideas you truly care about is also how you grow a loyal audience. Thanks to the algorithmic nature of Twitter, YouTube, and SEO, truly great and authentic content eventually surfaces over time.

If you're looking to learn about content distribution, here's my guide .

3. Blocker: Fear of being judged

Some writers fear their writing opens them up to attack: they worry that if a reader finds fault in their writing, they are finding personal fault in the writer.

If you're frozen by the fear of judgment, you can hedge against it:

  • Add a disclaimer to your writing: "I'm sharing early thoughts. I encourage readers to share their own experiences to help refine my thinking."
  • Instead of sharing original ideas, curate those of others'. Many newsletters, blogs, and Twitter accounts exclusively curate third-party content. Over time, you can weave your original thoughts alongside the curated ones. Continually increase the portion that's original until you're comfortable being a dominant voice at the forefront.
  • Write under a pseudonym. Widely-read blogs like Slate Star Codex and The Last Psychiatrist don't publicize their authors' names. This hasn't deterred millions of readers from finding and loving their work. Over time, as you acclimate to readers' reactions, you could transition to your real name.

Candidly, an unspoken ingredient to writing success is having a bit of shamelessness about getting things wrong in public. Too much shamelessness means you're a charlatan. But too little means you'll never publish.

No blogger is always right. Accept it.

4. Blocker: Procrastination

If you procrastinate occasionally, that’s normal—forgive yourself. However, if you procrastinate endlessly, that’s a problem.

Overcoming short-term procrastination

Procrastination is the result of two reflexes:

  1. Indulging in immediate rewards like browsing YouTube instead of writing.
  2. Avoiding work you perceive to be uncomfortable or tedious.

Let's tackle these two blockers.

1. Avoid distractions

Have you noticed how much writing we can get done on airplanes—despite having our knees and shoulders uncomfortably squeezed together for hours? Why is that?

It's because there's nothing else to do on an airplane.

This reveals a contrarian truth about writing: needing a comfy chair, room, or "the right ambience" is a myth. If you're waiting until your room is the right temperature to begin writing, you're lying to yourself.

Your blocker is not comfort, but rather distractions. Two strategies:

  • Listen to flow-inducing music — I listen to atmospheric music with a steady beat and without vocals. Here’s my Spotify playlist that works wonders. It reduces the occurence of errant thoughts popping into my head. Errant thoughts are what lead to time-wasting YouTube searches.
  • Remove the Internet — Disconnect from WiFi and leave your phone in another room. For most people, this isn't optional.

2. Speed past tedium

One trick for getting yourself to write is to only write sections that immediately interest you. Perhaps it's the middle of a post—that's okay. You don't have to write in order.

Sit down and write any three paragraphs you can. And do it fast. You'll find that by forcing yourself to start with speed, momentum carries you forward.

If this doesn't work for you—and you find yourself procrastinating for months—you may have one of three underlying problems:

  • You're not willing put in the effort to find interesting things to say.
  • You don't want to be a writer badly enough. You don't see the ROI in it.
  • You chose a topic you’re not sufficiently passionate about. Choose another.

Blockers recap

  • Focus on the ideas you can't get out of your head.
  • If you're concerned about being judged, use a pseudonym.
  • When struck by inspiration, sit down and speed through a few paragraphs.
  • Don't worry about whether people read your work. Writing is first and foremost a process for clarifying your own thinking. Readership is a bonus.

logic and clarity succinct and intriguing

.

Dissect good writing

To learn what a job well done looks like, dissect your favorite posts: highlight the best and worst parts of each and identify what makes them so.

Writers who post frequently (say, twice weekly) are rarely worth reading consistently. I read for insights. And no writer can generate profound insights on a fixed schedule. I aggregate writers who publish sporadically. When they post, they truly have something to say.

From the writer's perspective, frequent writing is good for building a writing habit and improving writing skills. But that's mutually exclusive from my point.

Writers I like

The past few years have shown that the Shakespeares, Twains, and Austens of the future won't emerge from the book publishing industry. They’ll come from YouTube, podcasts, and blogs.

Here are some of those contenders:

The difference between good writers and bad writers is good writers know when their writing is bad.
—Dan Brown

+

First, read the post below in its entirety. Then, re-read it while referencing my commentary underneath.

My dissection

1

  • Starts with an insight. Zero preamble. You know this article will be succinct.

2

  • He's signalling that his objective is to challenge a widely held belief. He states the status quo with a hint of sarcasm to imply he's about to demolish it.
  • He's writing in a conversational style to improve flow and help his voice shine through: 1. "How to explain" is awkward phrasing — it would normally be "How do we explain?" But he's choosing to write like he speaks. 2. "Well," is filler that would normally be cut, but he includes it to echo the call-and-response rapport you'd have in conversation. 3. "Kind of" is the conversational way of saying "somewhat."

3

  • Neither of these two sentences are necessary to make his point, but they build stakes and anticipation for the punchline — so that you better appreciate it once it comes. He's telling you a story, and no good story skips a good setup.

4

  • This is the punchline: the insight that our perspective on physics being the uniquely sensible choice had no good reason to be believed in Newton's time.
  • Lesson learned: We must assess past views and accomplishments in the lens of their time.

5

  • Ends with a poignant takeaway that prompts readers to reflect.
  • Uses staccato sentences to add emphasis and require readers to slow down.
  • "Risky" is both the last word in the body and the first word in the title. It's the point of the post: The biggest breakthroughs require taking the biggest risks.
  • He chooses not to explore the implications of risk. His post is focused: He succinctly makes a novel point then lets readers work through its implications.

Writing examples

Below are blog posts that exemplify the topic objectives:

  1. Open people’s eyes by proving the status quo wrong. Example .
  2. Share a solution to a tough problem. Example .
  3. Distill an overwhelming topic into something approachable. Example .
  4. Tell a suspenseful and emotional story that imparts a lesson. Example .
  5. Articulate something everyone’s thinking about but no one is saying. Cut through the noise.
  6. Identify key trends on a topic. Then use them to predict the future.
  7. Contribute original insights to a field through your research and experimentation.

The wonder of writing

What an astonishing thing a book is. It’s a flat object made from a tree with flexible parts on which are imprinted lots of funny dark squiggles. But one glance at it and you’re inside the mind of another person, maybe somebody dead for thousands of years. Across the millennia, an author is speaking clearly and silently inside your head, directly to you.
—Carl Sagan

Cheat sheet

Below is the cheat sheet for this entire handbook.

If you enter your email below, the cheat sheet is emailed to you so you can easily reference it in your inbox. You'll also be notified when my next guide is out.

If you liked the quality of this handbook and want to learn how to play piano or how to write fiction , get excited because I'm releasing those handbooks next. You can get them a couple months early via email:

Twitter .

Writing process

  1. Choose a topic
  2. Write your intro, and use it to brainstorm talking points
  3. Get feedback on your intro
  4. Create a starting outline
  5. Explore talking points within your outline
  6. Rewrite for clarity, succinctness, and intrigue
  7. Cycle between rewriting, resting, and receiving feedback
  8. Copy edit for grammar, word choice, and flow

Objectives

  • 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. 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.

Motivations

  • 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?

Introductions

First draft steps

  1. Choose an objective for your post.
  2. Write a messy braindump of your ideas.
  3. 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?
  4. 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.

Clarity

  • 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.

Succinctness

  1. Rewrite sections from memory. Focus on the key points and let the fluff fall away.
  2. Then remove unnecessary words from each paragraph.
  3. Then rephrase paragraphs to be as succinct as possible.

Intrigue

  • 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.

Feedback

  • 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.

Style

  • 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.

Copyediting

  • 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

  • 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.

Learn how to practice writing and rewriting. Aim for quality of input over of quantity of output. And find authors whose work you enjoy, then reverse engineer what makes them great.

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Writing Julian Shapiro
over 1 year ago
over 1 year ago

Everyone would do well to keep in mind that journalism is a speculative industry, so whether it’s a hit piece on a certain mostly reconstructed scene or a puff piece on a certain mostly reconstructed scene, the reality of what it’s trying to sell you is always highly unremarkable

Saved to
Writing Anna Khachiyan
over 1 year ago
over 1 year ago

Don't wait for an idea to be fully formed before writing. You write in order to think through the idea. The act of writing compels your brain to connect the dots.

Saved to
Writing Julian Shapiro
over 1 year ago
over 1 year ago

Be clear, succinct, and compelling. Your writing is clear once your ideas are self-evident. Your writing is succinct once everything unimportant is removed. Your writing is compelling once the reader effortlessly makes it to the end.

Saved to
Writing Julian Shapiro
over 1 year ago
over 1 year ago

Analogies help your ideas pop off the page. One way to write an analogy: • Make a comparison (red) • Explain the comparison (green) • Delight readers with the significance of it (blue) pic.twitter.com/FwqsPLTaMi

90% of writing is rewriting. It's a lot of work to rewrite. Meaning, being a consistent writer has less to do with finding the time and more to do with falling in love with the rewriting process. Make a game out of it: How can you make your ideas 20% clearer on each pass?

Saved to
Writing Julian Shapiro
over 1 year ago
over 1 year ago

Simplification such as this does not make your writing less sophisticated. The complexity of your writing should emerge from the strength of its ideas, not from how those ideas are worded.

Saved to
Writing Julian Shapiro
over 1 year ago
over 1 year ago

My upcoming thread is on how I write second drafts.

Saved to
Writing Julian Shapiro
over 1 year ago
over 1 year ago

Recap 1 of 2: • I write the worst draft I can as quickly as I can. Speedrun. • I use placeholders (<to fill>) any time I'm stuck. • The goal of my first draft is to generate and connect just a few good ideas.

Saved to
Writing Julian Shapiro
over 1 year ago
over 1 year ago

Recap 2 of 2: • When discovering my thoughts, I keep asking: How can I make this point more convincing? What are the interesting implications of what I just said? • Identify your writing objective. Pair it with a motivation. Have a north star.

Saved to
Writing Julian Shapiro
over 1 year ago
over 1 year ago

This brings us to the writing framework I use. It goes like this:

Saved to
Writing Julian Shapiro
over 1 year ago
over 1 year ago

Speaking of outlines. I outline depending on my writing intent: 1. Am I writing to share information I already know? If so, I outline. 2. Am I writing to think through ideas? If so, that means I'm writing to discover. I skip the outline and freely explore my thoughts.

Saved to
Writing Julian Shapiro
over 1 year ago
over 1 year ago

This is why the new novels die so quickly, and why the old fairy tales endure forever. The old fairy tale makes the hero a normal human boy; it is his adventures that are startling; they startle him because he is normal. But in the modern psychological novel the hero is abnormal.

Saved to
Writing GK Chesterton
over 1 year ago
over 1 year ago

We hear much today about modern books which "make you think." In my experience it is rather rare to find a modern book that even allows you to think. Modern books perpetually present, not the wrong answer, but the wrong question.

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Writing GK Chesterton
over 1 year ago
over 1 year ago
Video

Chesterton Books That C.S. Lewis Owned

over 1 year ago