Julian Shapiro


How to rewrite bad writing 👇 After rewriting 400,000 words on my site... Advice for blog posts, tweets, emails:
Great authors’ first drafts are bad—no better than yours. However, they aggressively *rewrite* those drafts.
Your first draft is for messily generating ideas. Your second draft is for identifying the best ideas then making them resonate. The enemy of rewriting is being precious about what you originally said and how you originally said it. You need to be willing to destroy.
Part 1. Write to be understood Readers don't assess the quality of nonfiction by its elegance nor its complexity. Instead, they assess: [How strong your ideas are] x [how intuitively they understand them] Unclear sentences distract from that understanding.
Technique #1: Use 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 the details. Rather, children must be able to follow the logic of every argument.
When talking to children, notice how you instinctively simplify: • You use plain phrasing. • You use fewer ideas per sentence. Use these techniques in your writing too.
For example, here’s a sentence with overly-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."
I removed abstract words like "charted" and "landscape," and I reduced a conceptual idea into a specific example. By removing overhead, the underlying point stands out.‍ The complexity of your writing should emerge from the strength of its ideas—not the wording.
Part 2: Rewrite for succinctness ‍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. (Thanks to @paulg for this.) A post can be 50,000 words, but if it's dense with insights and devoid of rambling, it's succinct.
Here are three steps I use to achieve succinctness.
Step 1: Rephrase entire sections For each section of your post: • Read all its paragraphs. • Take an hour-long break. • 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 when 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 point resonate.
Succinctness Step 2: Rephrase paragraphs The art of rewriting is the art of becoming self-aware about the purpose of every word you've written. • Remove ideas that aren't critical to the central point. • Don't describe what doesn't need to be described.
Eg. Decent 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 exhaust readers, they quit reading."
Let's rephrase it for more succinctness: "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.
Part 3: Writing something great Clarity and succinctness are what help ideas resonate. They reduce the friction of reading. But it’s *intrigue* that gets people to read in the first place.
Intrigue is generated in two ways: 1. Novelty — A claim that's counter-intuitive, counter-narrative, surprising, or elegantly poetic. Novelty = New info that readers would not have easily intuited on their own.
2. You can also generate intrigue by withholding information: Tease readers with a question you don't answer until later. If you weave (1) novelty and (2) withhold information, readers are likely to remain engaged. @waitbutwhy is great at this.
Here's my technique for interweaving novelty. • Ask feedback-givers to highlight every sentence that gives them a dopamine hit. Those are the moments of novelty: "Ahh, that's interesting." • For each hit, increase a counter at the end of its sentence. Like this (3).
• Then, if there are long stretches without dopamine hits, make those sections more concise—or inject more novelty into them. • Rinse and repeat until your article has a steady cadence of dopamine hits.
For an example of a post with a lot of dopamine hits, see the pinned tweet on my Twitter profile: @julian
Now for the most interesting technique for generating intrigue. I want you to consider two psychological principles. 1. The hook principle — "A captivating intro buys goodwill with readers so they overlook an imperfect middle."
2. 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 provide a simple cheat code to great writing: 1. Have a captivating intro that buys goodwill. 2. Have at least one sustained peak of insight or surprise. 3. Have an ending that satisfyingly justifies why the piece was worth reading.
Takeaways: • Use simple wording and simple sentences. • Simple language doesn't weaken ideas. It strengthens them by helping what matters stand out. • Evenly distribute dopamine hits. Rely on feedback; it's hard to judge this yourself.
I post threads 2x/week like this. If you want more writing content, you can give me a follow and turn on notifications. See my past threads here: @julian
"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 (@neilhimself)
This thread is only a high-level intro. For specifics, see my handbook. It's free, and I have nothing to sell you: https://t.co/BJkEXDWUxr