This is the last page of a guide to WritingWell. Start at page one.
Key learnings from this guide
Your goal is not to foster the writing habit. Your goal is to fall so in love with ideas that you can’t not write about them. Find your objective and your motivation.
Don't fully think through your ideas before writing. It's inefficient. The best way to think is by writing. It compels your brain to connect the dots.
When rewriting, you alternate between being a loving nurturer of your writing and being a ruthless military general forcing it to be better.
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.
Treat feedback as a science. Measure your scores and iterate. Remember that the best feedback often comes from you with fresh eyes.
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.
Disclaimer: 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:
I had strong opinions to express and nagging questions to answer.
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.
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:
Indulging in immediate rewards like browsing YouTube instead of writing.
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.
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.
"If people cannot write well, they cannot think well. And if they cannot think well, others will do their thinking for them." —George Orwell
Don't practice writing by targeting a weekly output of words or posts. Output volume measures your busyness instead of your improvement.
Cadence is still useful for forcing yourself to overcome the friction of writing, but your primary goal should be making your writing increasingly persuasive or resonant. That's how you hone your eye for rewriting.
Persuasive writing requires logic and clarity. If you’re neither, readers cannot follow your arguments to become convinced of them. And if you fail to be succinct and intriguing, readers quit before digesting your full argument.
But what should you write about? Simply ask yourself, What's bothering you most right now? Write a post where you work through that—and get to a conclusion.
This is how I start every time. Writing is therapy that you publish for the world to learn from.
Note that I share a lot more advice on honing your writing on my Twitter feed.
Write short posts that persuade your friends to change their minds.
Ask them to score from 1-10 how much your writing sustained their interest.
Rinse and repeat until you're regularly churning out 7.5+ posts.
Make this is a game, not a chore
Great writers make a game out of rewriting:
How young of a reader can I successfully convey my argument to?
How many unnecessary words can I delete?
How much of a page-turner can I make this?
How much higher can I push my feedback score out of 10?
The more posts you run this process on, the better the writer you become. Personally, I believe I wrote 30 posts before rewriting finally clicked for me.
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
If you love a writer because their work elegantly captures how you feel about the world, you're reading for entertainment.
If instead you love a writer because they challenge your perspective and expand your thinking into new territory, then you're reading for education.
With that in mind, here are writers whose work entertains and educates me:
First, read the post below in its entirety. Then, re-read it while referencing my commentary underneath.
Starts with an insight. Zero preamble. You know this article will be succinct.
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."
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.
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.
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.
Below are blog posts that exemplify the topic objectives:
Articulate something everyone’s thinking about but no one is saying. Cut through the noise. Example post.
Identify key trends on a topic. Use them to predict the future. Example.
Contribute original insights through research and experimentation. Example.
Distill an overwhelming topic into something approachable. (This guide.)
Tell a suspenseful and emotional story that imparts a lesson. Example.
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
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Choose a topic
Write your intro, and use it to brainstorm talking points
Get feedback on your intro
Create a starting outline
Explore talking points within your outline
Rewrite for clarity, succinctness, and intrigue
Cycle between rewriting, resting, and receiving feedback
Copy edit for grammar, word choice, and flow
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.
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?
Start your brainstorming process by prematurely writing your intro. In discovering how to make your intro interesting to you, you'll also discover how to interest and hook readers.
Hooks are half-told stories. Tease something fascinating, but don’t fully reveal the details.
How to generate hooks: (1) Ask yourself, “If someone else wrote my intro, what are the most captivating questions they could pose to make me excited to read this?” (2) Write those questions down. Even if you lack the answers. (3) Rank your questions by how much they interest you. (4) The top questions become your hooks: Pose them in your intro and don't reveal their answers.
Ask others for feedback after you've written your intro. Sanity check your hooks.
If feedback-givers have skepticisms, proactively address them in your intro. And if they have other questions they care about, swap them in if they captivate you too.
Browse the list of skepticisms and their solutions here.
First draft steps
Choose an objective for your post.
Write a messy braindump of your ideas.
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?
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.
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.
Rewrite sections from memory. Focus on the key points and let the fluff fall away.
Then remove unnecessary words from each paragraph.
Then rephrase paragraphs to be as succinct as possible.
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.
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.
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.
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 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.
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