Rewriting

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

Rewriting

Your first draft is for messily generating novel ideas. Your second draft is for filtering the best ideas then making them resonate.

Even your favorite authors’ first drafts are bad—no better than yours. However, they have the discipline to aggressively rewrite their first drafts in pursuit of:

  1. Logic — Persuasive thinking
  2. Being clearly understood — Clear articulation with examples
  3. Sustaining curiosity — Novelty doled out succinctly
  4. Resonance — Story, analogy, and poetry (covered on the next page)

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, know that you do so in whatever disjointed way immediately comes to mind. Rewriting is the craft of finding the puzzle pieces within that mess—then putting them together in the right order.

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

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.

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

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

Overwritten, unclear sentences distract from that understanding.

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:

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 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.

One last example:

Bad — "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."
Good — "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. Ask if you don’t know what they are. Afterward, when someone proposes an idea that doesn’t make sense to you, think through the idea using their frameworks as a lens. Work backward from there to build empathy."

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.

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

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

In my experience with talented students of writing, the most important thing for them to remember is that someone who is not them and cannot read their mind is going to have to read this... The reader cannot read your mind.
—David Foster Wallace

2. Sustaining curiosity — Succinctness

After you've rewritten your article for clarity, you’re left with a better understanding of what you’re trying to say. The fewer words you use, the more those that remain stand out.

The next step is rewriting for succinctness: remove everything you now realize is not required to make your point.

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

How to be succinct

Novice writers mistake 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 think they’re supposed to hit.

That works in conversation, but that's not how good writing works. Writing is a process of deliberate thought curation—where each sentence must justify its existence in your final draft.

I once stumbled upon an Amazon book review that helps make my point. It was one of the dumbest reviews I've read:

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

Actually, your $15 got you 100 pages plus 3 hours of your time back. A 100 page book is a book without 200 pages of needless filler. The author did you a favor. They understood that while words are free for them, they're costly for the reader.

After a deliberate writer has written something, they ask:

Then, when they get stuck, they generate more ideas by asking:

1. Step 1: Rewrite entire sections

I cut filler from my writing using 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.

A related approach is to call a friend: Have them read your draft.  Ask them to 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 summary resonate.

I call these verbal summaries and they're the secret weapon to succinctness.

Example: Verbal summary+

Original

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.

Verbal summary

Incentives between employees and companies are misaligned by default.

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 opportunities and the opportunities that create an outsized impact at your company. Then argue for your right to exist at the intersection.

You need to carve your own journey instead of blindly climbing the corporate ladder.

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.

2. 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. We need to fix two things:

The art of rewriting is the art of becoming self-aware about the purpose of every word you've written.

Let’s rewrite the paragraph 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 saying becomes clearer. We've narrowed into what we're really trying to say.

3. Step 3: Rephrase paragraphs from scratch

When key points become clear, you're in a position to fully rephrase your paragraphs for additional clarity, succintness, and punchiness.

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.

We've defended against readers abandoning our writing. When filler is removed, readers sustain momentum: they make it to the end without pausing to wonder what's new on YouTube.

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

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

Intrigue is the quality most responsible for reader satisfaction. It's driven by hooks and punches:

If this pattern sustains throughout your post, readers remain engaged.

I have two techniques for doing this.

1. Dopamine counting

The first technique is what I call dopamine counting:

A dopamine hit is triggered by novelty. For an idea to be novel, it needs to be new information that:

If you've read this far, dopamine counting is the technique that 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)

Here's an interview where Ed talks about it.

2. Withholding information

The second technique for sustaining intrigue is selectively withholding information.

This is also how stage magic works: card tricks would be less interesting if you were shown upfront how they worked.

Stories function the same way: storytelling is the art of choosing what to withhold. When rewriting, decide which answers you want to reserve until the end.

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 help 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.

That’s it. There’s your 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 appreciate 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 craft your article’s peak, simply condense your most insightful and surprising talking points into one section. Build 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.

Place gold coins along the path.
—Roy Peter Clark

Takeaways

I share more rewriting advice on my Twitter.

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. 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
The final page has a cheat sheet that recaps all the advice in this handbook.

Feedback

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

You ask for feedback.

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

Conversely, when giving feedback, it's also the most efficient way to hone your eye for rewriting: giving deep, critical feedback on others' writing internalizes the learnings in this handbook.

Asking for feedback

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

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

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

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

3. Tell me what isn't clear.

When you're done reading, please score this from 1-10 on how satisfying of a read 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, which is important to me.

Keep rewriting until you average a score of 7.5+ across a handful of respondents. That puts you in the "this was a worthwhile 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 a many good ways to tell a story. Be happy when you’ve found one that’s very good.

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.

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

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 improved understanding of the topic.

When people tell you something's wrong or doesn't work for them, they are almost always right. When they tell you exactly what they think is wrong and how to fix it, they are almost always wrong.
—Neil Gaiman

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.

Next page

Page IV — Adding style and voice

Make your writing resonate. Make it personal.

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