This is page three of a guide to Writing Well.
Your favorite authors’ first drafts are typically bad too. However, great authors have the discipline to aggressively rewrite their first drafts in pursuit of:
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 the correct 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.
The process of writing your second draft is the process of making it look like you knew what you were doing all along.
When rewriting, one of our goals is to be understood.
Readers don't assess the quality of nonfiction by its elegance nor its complexity. Instead, the quality of nonfiction emerges from:
How strong its ideas are x how much those ideas resonate
You get in the way of resonating when your ideas are unclear.
Clear writing starts with clear thinking:
We'll explore two tools for accomplishing this:
I like to 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 and nuances. Rather, I think children should be able to follow the logic of all your arguments.
You already do this intuitively. When speaking to children, you simplify:
We're going to use these techniques in our writing too.
Here's a sentence with complex phrasing:
"The obstacle facing media organizations is charting an economically sustainable course through a landscape of commodity journalism.”
Let’s rewrite that plainly:
“News companies are struggling to stay in business because anyone with a Twitter account can report the news now. The news has never been more of a commodity than it is today."
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 represented a concept with 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."
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 an obstacle. You only fully understand the context of a sentence when you're 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.
I'm okay with letting difficulty emerge from uncovering the implications of what I write. But I'm not okay with making it difficult to understand what I'm trying to say in the first place.
When you keep your language simple, you can get away with making your ideas infinitely complex.
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:
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.
After you've rewritten your draft for clarity, you’re left with a better understanding of what you're trying to say. At this point it's easier to rewrite for succinctness: remove everything you now realize is not required to make your point.
Succinctness—a lack of bloat—helps readers finish your post. What I've learned from asking a lot of friends for feedback is that readers often quit not because they dislike your ideas, but because they're bored.
Succinctness is a ratio. It's the percentage of significant thoughts out of all the thoughts communicated. A post can be 50,000 words, but if it's dense with true insights and devoid of unnecessary words, it's succinct.
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.
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 can justify its inclusion in your final draft.
When a deliberate writer has written something down, they then ask:
Later, when they get stuck expanding on their ideas, they ask:
Here is my three step process for being succinct.
For each section of an article, I will:
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.
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. By starting with our succinct summary, it makes it easier to identify where adding story will be additive and not just redundant.
By this step, we've rewritten each section to succinctly convey our key points.
Now we rewrite sentence-by-sentence to remove unnecessary detail. The art of rewriting is the art of becoming self-aware about the purpose of every word.
After we remove unnecessary words, we'll rephrase what remains to be even more succinct.
First, 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:
Let’s rewrite that 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.
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 less long and boring.
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.
Off topic: This year, I got tired of overlong books and bad book summaries. So I made a newsletter that just shares the most interesting highlights from famous books. I distill each book's key lessons into short paragraphs. 50,000 people read it. Subscribe to see the first issue. I only email once per month.
"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."
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.
Clarity and succinctness help ideas resonate. They reduce mental overhead so your ideas pop.
But what gets people reading in the first place? Intrigue, which is the other quality we rewrite for.
I use two techniques for generating intrigue:
We're taking the elements that made our intro hooks so compelling and dispersing them throughout our entire article. This helps readers stay engaged.
I use a technique I call dopamine counting to weave novelty into my writing:
If you've read this far, dopamine counting is what got you here.
Below is my Creativity Faucet blog post. I shared this with friends and asked them to indicate which parts gave them dopamine hits.
One of the most valuable writing skills is the ability to generate novel ideas.
Last year, I stumbled into a mental model to achieve this at will.
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 get curious. (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, write out every bad idea that reflexively comes to mind. Instead of being self-critical and resisting these bad ideas, accept them.
Once the bad ideas are emptied, strong ideas begin to arrive.
Here's my guess as to why: Once you've generated enough bad output, your mind starts to reflexively identify which elements caused 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 treat the brain as a pipeline for entering a creative flowstate, and they never forget that the pipe needs clearing. In every creative session, they allot time for emptying the wastewater.
They're not worrying whether clear water will eventually arrive. It always does: (7)
Mozart had 600 musical compositions and Edison had 1093 patents. Only a few are remembered today, and that's the point.
The second technique for sustaining intrigue is withholding information.
Storytelling is essentially the art of choosing what information to withhold. When rewriting, decide which answers you want to reserve until the end.
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:
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.)
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.
To craft your article’s peak, simply condense your most insightful and surprising talking points into one section. Build that climax.
Let's resituate you within this handbook:
A reminder that the last page of this guide has a downloadable cheatsheet that handily recaps everything you're about to learn.
Getting feedback is the most efficient way to improve your writing. This is not optional. Giving feedback is as important: giving it to others forces you to internalize the learnings from this handbook.
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.
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 with my own writing.
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 text editors 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.
Here are problems with my writing that I can best identify with the benefit of a break:
I spend thousands of hours deconstructing topics. I compile insights into handbooks (like this one). Over a million people read them annually. I also write threads on Twitter, which are read by millions every year.
Readers enjoy my writing for its density of insights and its concision.
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.
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.
This year, I got tired of overlong books and bad book summaries. So I made a monthly newsletter that just shares the most interesting highlights from famous books. I distill each book's key lessons into short paragraphs. 50,000 people read it. Subscribe to see the first issue.
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