How to Rewrite

This is page three of a guide to Writing Well. Start at page one.


Your favorite authors’ first drafts are bad — no better than yours.

However, they aggressively rewrite their first drafts.

They know that when an idea is first written down, it’s articulated in whatever disjointed way immediately comes to mind.

So they rewrite it in pursuit of four objectives:

  1. Clarity
  2. Succinctness
  3. Intrigue
  4. Logic

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

While rewriting, consider listening to atmospheric music. It helps reduce your susceptibility to distraction. A steady beat without vocals helps put you in a trance. You can follow my atmospheric 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


Readers don't assess the quality of your writing by its elegance nor sophistication. Instead, they assess based on a simple equation:

Quality = How strong your ideas are x how intuitively they understand them.

Overwritten sentences distract from that understanding.

Ideas and clarity are everything.

What is clarity?

Writing is clear when readers can understand it without effort.

It’s okay to make readers work through the implications of what you’re saying, but it’s not okay to make them piece together what you’re saying in the first place.

Clear writing starts with clear thinking:

  1. What am I really trying to say?
  2. What is the key point I need to make?
  3. How can I make that key point easy to understand?

We'll explore two tools for increasing clarity:

Simple sentences

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

If they can understand you, so can everyone else.

That isn't to say children should understand your references and jargon. Do not over-simplify your language and weaken your ideas. Rather, children must be able to follow the logic of every argument.

While talking to children, you instinctively simplify:

Use these techniques in your writing too.

Use plain phrasing where possible.

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 grammatical overhead, the underlying point stands out.

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.

Just don't drop key information while simplifying. This, for example, would be bad:

"News companies are not doing well today."

That loses the point of why news companies are not doing well.

Simplify your sentences without dumbing down your ideas.

Use fewer ideas per sentence.

There's another simplification technique you use when talking to children.

Consider this bad paragraph:

“There is 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 a lot of research on gut bacteria. We’re quickly learning what roles bacteria play and how they interact with each other. Researchers want to better understand how these bacteria 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 a complex point even harder.

Don't be mean to your readers. Make it effortless to read your words.

Beware rephrasings

When authors restate a point, they point it out:

“In other words…”
“That is to say…”
“Put another way…”

These are often red flags: the point that came before needed to be rephrased to be understood.

Instead, delete the rephrasing and reword the original statement to be self-evident: use plain wording and use fewer ideas per sentence.

If simplification can't achieve the necessary clarity, it's time to provide examples.

Anything that can be said can be said clearly.
– Ludwig Wittgenstein

Provide examples

Providing examples is another tool for improving clarity. Examples make abstract statements specific. Your brain best remembers things this way.

A few tips for providing examples:

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

Takeaways for clear writing


After you've rewritten your article for clarity, you’re left with a better understanding of what you’re trying to say.

That’s when you can rewrite it for succinctness: remove everything you now realize is not required to make your point. Further, remove everything that's redundant. And remove everything that's redundant.

Succinctness is a ratio. It’s the number of meaningful words per paragraph — regardless of how many paragraphs there are.

How to be succinct

The dumbest Amazon book review:

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

Actually, your $15 got you 100 pages plus 3 hours of your life back. Because a 100 page book is a book without 200 additional pages of needless filler.

The author did you a favor.

Words are free for the author, but costly for the reader. Treat words like gold coins — not as an unlimited supply.

Step 1: Rewrite entire sections

You cut filler from your writing with a three-step process.

For each section:

  1. Read all its paragraphs.
  2. Take an hour-long break.
  3. Rewrite the section from memory — focusing only on key points.

The version written from memory will take a more direct path toward your points. The fluff falls away while you focus on trying to effectively re-articulate your idea.

Step 2: Remove unnecessary words

Next, go through each sentence in your rewritten section.

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: these 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.

Stop. That was a terrible paragraph. Let’s rewrite it without its unnecessary words:

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 the unnecessary words removed, what we're trying to say is clearer.

This helps you accomplish your final step.

Step 3: Rephrase paragraphs from scratch

Your last step is to succinctly rephrase what remains. This means removing descriptions of things that aren't critical to your central point. Don't describe what doesn't need to be described.

Again, here’s what we have:

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.


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.

This protects against readers abandoning half your articles (Source).

When filler is removed, readers gain momentum: they make it to the end without pausing to wonder what's new on YouTube.

Step 4: Remove redundancy

Re-read your article. Delete and re-order ideas as needed to remove unnecessary repetition.

The Tweet test

After writing a post, I try compressing it into a single tweet. If I can pull that off, 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.

"How long does it take you to prepare a speech?" asked a friend of President Wilson. "That depends on its length," answered the President. "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.


The reason we endlessly seek life and career advice from books and Twitter is not because we‘re seeking new advice. By our mid-twenties, we’ve heard much of it.

We seek advice because we’re lazily waiting for someone to package it in such an intriguing and resonant way that it ignites us into taking action.

Intrigue is the quality most responsible for reader satisfaction. When you're highly intriguing, readers overlook your lack of clarity and succinctness.

Two qualities make your writing intriguing: insights and surprises.

The psychology of intrigue

Recall my psychological principle for introductions:

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

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 guarantee readers enjoy your 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.

That’s it. There’s your formula for intriguing writing. 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.

Applying the peak-end rule to cinema: Many boring indie films are held together by an intensely poetic scene and a cathartic ending. That’s all they need for people to love 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, and lean into what excites you.

To form your article’s peak, simply condense your most insightful and surprising talking points into one section. Craft a climax.

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

Sustaining intrigue in long pieces

A reader's goodwill eventually fades. The longer your article, the greater you work to sustain intrigue.

I do this with a technique I call dopamine counting:

If you've read this far, dopamine counting is the technique that got you here.

Place gold coins along the path.
– Roy Peter Clark


Where you are

Let's re-frame where you are:

  1. Choose a topic
  2. Write your intro, and use it to brainstorm talking points
  3. Get feedback on your intro
  4. Explore your talking points in your first draft
  5. Rewrite the body for clarity, succinctness, and intrigue
  6. Cycle between rewriting, resting, and receiving feedback ←  You’re here
  7. Copy edit for grammar, word choice, and flow
The next page has a cheat sheet that recaps all the advice in this handbook.


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

How do you know when your writing is bad?

You ask for feedback.

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

It's also the most efficient way to hone your eye for rewriting: giving deep, critical feedback on other people's writing internalizes the learnings on this page.

Asking for feedback

Ask for feedback from the audience you’re writing for: Have them score how satisfied they are between 1 and 10 after reading your article.

Keep rewriting your article until you average 7.5+ across a handful of respondents. That puts you in the "interesting article" category.

Do not waste time on perfection. It's impossible to get a 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.

Please share your feedback on this handbook using this form.


Here’s a template for requesting feedback:

Could you score this from 1-10 on how satisfied you were after reading it?

Don’t be afraid to give me a low score. The more people tell me this isn't good yet, the more I'm motivated to make it even better.

Also, feel free to point out any problems and to suggest ideal fixes:

— What didn’t you agree with?
Clarity — What was unclear?
Interest — What bored you?
Brevity — What unnecessary things should be removed?
Expansion — What unanswered questions were you left with?

Send this to a diverse group of people. You want businesspeople, poets, teenagers, wise elders, and everyone in between to provide their perspective.

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

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.

Take it from 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 found a week is often enough time to sufficiently defamiliarize myself.

I've also found that switching mediums tricks my brain into re-reaing my work with a new set of eyes: If I wrote the first draft in Dropbox Paper, for example, I'll write the second 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.

Incorporating feedback+

A few rules of thumb for incorporating feedback:

I consider my writing done when:

You can always make your article better, but you'll encounter diminishing returns quickly. Just get to a point where you're happy with it and your objective is fulfilled, then move on for now.

If you're like me, you'll get pleasure out of revisiting old pieces every few years and updating them to reflect your latest wisdom.

Addendum: Style+

Style has three components:

Pardon me while I open a wormhole into your brain and thrust style advice into it.

See, that’s an example of style. I could have just said: "And now let’s learn about style."

Style is voice

How would your friends describe talking to you? Perhaps they’ll mention your:

Convey those same traits in your writing, and readers will recognize your voice.

The more authentic your voice, the more they'll relate.


If you're comfortable doing so, practice being radically honest: Discard your reflex to self-censor. Reveal your vulnerabilities. Talk like you do with friends.

Even bad writing is enjoyable when the author writes like they’ve known their reader since childhood. It’s a breath of fresh air. It feels personal.

Authenticity is also half the recipe for memorability: the combination of vulnerability and profound insights makes for an unforgettable article. It makes readers pause and seek out your newsletter or Twitter account.


Inauthentic voice happens when you read a lot of someone else’s work and absorb their style.

Writers also absorb fake prestige: They use words like "plethora" and “myriad.” But if they don’t use those words in conversation, they shouldn’t use them in their writing. They’ll just look pretentious.

The antidote to inauthenticity is reminding yourself how you talk with friends. Record yourself talking, transcribe it, and work off that.

"The authenticity of who you really are, as opposed to who you wish everyone thought you were, is what your audience is looking for." — C. Robert Cargill

Style is presentation

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

Would analogies, anecdotes, humor, or multimedia better entertain your readers or help convey your points? If so, consider using them.

Style is creativity

Style is also creativity, which is the art of delighting readers with poetic thought and language.


The vividness of writing is analagous to cranking the saturation dial on an image.

Blogger Venkatesh Rao remarks on the vividness of writer 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."

As an example, let's look at a plain sentence:

I sat in the new office with a few other men. The furniture was hyper-modern and uninviting. Before me sat the Dean. He made his best effort to appear kind, and perhaps he was, but one thing was certain: he was firmly in control.

Now here's David Foster Wallace's vivid take:

“I am seated in an office, surrounded by heads and bodies. My posture is consciously congruent to the shape of my hard chair. This is a cold room in University Administration, wood-walled, Remington-hung, double-windowed against the November heat, insulated from Administrative sounds by the reception area outside... The Dean at left, a lean yellowish man whose fixed smile nevertheless has the impermanent quality of something stamped into uncooperative material, is a personality-type I've come lately to appreciate, the type who delays need of any response from me by relating my side of the story for me, to me."

— Infinite Jest by David Foster Wallace

Vividness is more than just detail. It's detail that resonates.


I like to define poetry as finding evocative and unconventional ways to make meaningful statements. For example, instead of saying "the day was hot," you could write that “even the bugs were looking for air conditioning.”

In that example, we're indirectly describing the effect caused by the object being focused on as opposed to directly describing the object and its status. In other words, it's a step removed from a straightforward telling of the events.

The more steps removed you can be while still successfully communicating your meaning, the more "poetic" your prose can feel. Further, the more profound your underlying point is, the more "deep" your prose feels.

Only the start

This isn't a complete breakdown of creative writing. The topic in its entirety is sadly outside the scope of this handbook.

Great examples of style


Addendum: Copyediting+

Copyediting is the process of combing through sentences word-by-word to:

This makes your writing only marginally better. Don't spend too much time on this.

Below, I'll cover:


If you write clearly and punctuate mostly correctly, you know all the grammar you need. If not, here’s my companion post on punctuation.

If you really want to dive into grammar, here’s the book to buy!

Visual density

Minimize adverbs and adjectives

Swap synonyms

Swapping words for their synonyms serves two purposes: enriching and reducing your language.


You enrich words by swapping them for new ones with greater specificity or emotional weight.

For example:

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


Reducing words is the opposite of enriching: it's reverting to more common language to make sentences easier to read.

For example:

“I obtained maximal status” could become “I reached the highest status.”
Or, “Her diction is brilliant” could become “Her word choice is brilliant.”

If the reduced word doesn't lack important details, use it. By default, keep sentences simple. After high school, no one pats you on the back for using big words.

There are three types of words: (1) words we know, (2) words we should know, and (3) words nobody knows. Forget those in the third category and use restraint with those in the second. — John Grisham

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 Together, they identify when someone has taken my work.

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