On Writing #1

This isn’t primarily about how I write. It’s about how other people write, and what advice they give on how to write, and how I react to and relate to that advice.

I’ve been collecting those notes for a while. I figured I would share.

At some point in the future, I’ll talk more about my own process - my guess is that what I do very much wouldn’t work for most people, but would be excellent for some.

Table of Contents

1. How Marc Andreessen Writes.

2. How Sarah Constantin Writes.

3. How Paul Graham Writes.

4. How Patrick McKenzie Writes.

5. How Tim Urban Writes.

6. How Visakan Veerasamy Writes.

7. How Matt Yglesias Writes.

8. How JRR Tolkien Wrote.

9. How Roon Wants Us to Write.

10. When To Write the Headline.

11. Do Not Write Self-Deprecating Descriptions of Your Posts.

12. Do Not Write a Book.

13. Write Like No One Else is Reading.

14. Letting the AI Write For You.

15. Being Matt Levine.

16. The Case for Italics.

17. Getting Paid.

18. Having Impact.

How Marc Andreessen Writes

Marc Andreessen starts with an outline, written as quickly as possible, often using bullet points.

David Perell: When Marc Andreessen is ready to write something, he makes an outline as fast as possible.

Bullet points are fine. His goal is to splatter the page with ideas while his mind is buzzing. Only later does he think about organizing what he’s written.

He says: “I’m trying to get all the points out and I don’t want to slow down the process by turning them all into prose. It’s not a detailed outline like something a novelist would have. It’s basically bullet points.”

Marc is saying that first you write out your points and conclusion, then you fill in the details. He wants to figure it all out while his mind is buzzing, then justify it later.

Whereas I learn what I think as I write out my ideas in detail. I would say that if you are only jotting down bullet points, you do not yet know what you think.

Where we both agree is that of course you should write notes to remember key new ideas, and also that the organizing what goes where can be done later.

I do not think it is a coincidence that this is the opposite of my procedure. Yes, I have some idea of what I’m setting out to write, but it takes form as I write it, and as I write I understand.

If you’re starting with a conclusion, then writing an outline, and writing them quickly, that says you are looking to communicate what you already know, rather than seeking to yourself learn via the process.

A classic rationalist warning is to not write the bottom line first.

How Sarah Constantin Writes

Sarah Constantin offers an FAQ on how she writes. Some overlap, also a lot of big differences. I especially endorse doing lots of micro-edits and moving things around and seeing how they develop as they go. I dismiss the whole ‘make an outline’ thing they teach you in school as training wheels at best and Obvious Nonsense at worst.

I also strongly agree with her arguments that you need to get the vibe right. I would extend this principle to needing to be aware of all four simulacra levels at once at all times. Say true and helpful things, keeping in mind what people might do with that information, what your statements say about which ‘teams’ you are on in various ways, and notice the vibes and associations being laid down and how you are sculpting and walking the paths through cognitive space for yourself and others to navigate. Mostly you want to play defensively on level two (make sure you don’t give people the wrong idea), and especially on level three (don’t accidentally make people associate you with the wrong faction, or ideally any faction), and have a ‘don’t be evil’ style rule for level four (vibe well on all levels, and avoid unforced errors, but vibe justly and don’t take cheap shots), with the core focus always at level one.

How Paul Graham Writes

I think this is directionally right, I definitely won’t leave a wrong idea in writing:

Paul Graham: Sometimes when writing an essay I'll leave a clumsy sentence to fix later. But I never leave an idea I notice is wrong. Partly because it could damage the essay, and partly because you don't need to: noticing an idea is wrong starts you toward fixing it.

However I also won’t leave a clumsy sentence that I wasn’t comfortable being in the final version. I will often go back and edit what I’ve written, hopefully improving it, but if I wasn’t willing to hit post with what I have now then I wouldn’t leave it there.

In the cases where this is not true, I’m going explicitly leave a note, in [brackets] and usually including a [tktk], saying very clearly that there is a showstopper bug here.

Here’s another interesting contrast in our styles.

Paul Graham: One surprising thing about office hours with startups is that they scramble your brain. It's the context switching. You dive deep into one problem, then deep into another completely different one, then another. At the end you can't remember what the first startup was even doing.

This is why I write in the mornings and do office hours in the afternoon. Writing essays is harder. I can't do it with a scrambled brain.

It's fun up to about 5 or 6 startups. 8 is possible. 12 you'd be a zombie.

I feel this way at conferences. You’re constantly context switching, a lot of it isn’t retained, but you go with the flow, try to retain the stuff that matters most and take a few notes, and hope others get a lot out of it.

The worst of that was at EA Global: Boston, where you are by default taking a constant stream of 25 minute 1-on-1s. By the end of the day it was mostly a blur.

When I write, however, mostly it’s the opposite experience to Graham’s writing - it’s constant context switching from one problem to the next. Even while doing that, I’m doing extra context switching for breaks.

A lot of that is presumably different types of writing. Graham is trying to write essays that are tighter, more abstract, more structured, trying to make a point. I’m trying to learn and explore and process and find out.

Which is why I basically can indeed do it with a scrambled brain, and indeed have optimized for that ability - to be able to process writing subtasks without having to load in lots of state.

How Patrick McKenzie Writes

Patrick McKenzie on writing fast and slow, formal and informal, and the invocation of deep magick. On one topic he brings up: My experience on ‘sounding natural’ in writing is that you can either sound natural by writing in quick natural form, or you can put in crazy amounts of work to make it happen, and anything in between won’t work. Also I try to be careful to intentionally not invoke the deep magick in most situations. One only wants to be a Dangerous Professional when the situation requires it, and you need to take on a faceless enemy in Easy Mode.

Patrick McKenzie also notes that skilled writers have a ton of control over exactly how controversial their statements will effectively be. I can confirm this. Also I can confirm that mistakes are often made, which is a Skill Issue.

How Tim Urban Writes

Tim Urban says writing remains very hard.

Tim Urban: No matter how much I write, writing remains hard. Those magical moments when I'm in a real flow, it seems easy, but most of the time, I spend half a day writing and rewriting the same three paragraphs trying to figure out the puzzle of making them not suck.

Being in a writing flow is like when I'm golfing and hit three good shots in a row and think "k finally figured this out and I'm good now." Unfortunately the writing muse and the golf fairy both like to vanish without a trace and leave me helpless in a pit of my own incompetence.

Dustin Burnham: Periods of brilliance would escape Douglas Adams for so long that he had to be locked in a hotel room by his editors to finish The Hitchhiker’s Guide to the Galaxy.

I definitely have a lot of moments when I don’t feel productive, usually because my brain isn’t focused or on. I try to have a stack of other productive things I can do despite being unproductive while that passes.

But over time, yes, I’ve found the writing itself does get easy for me? Often figuring out what I think, or what I want to write about, is hard, but the writing itself comes relatively easily.

Yes, you can then go over it ten times and edit to an inch of its life if you want, but the whole ‘rewriting the same three paragraphs’ thing is very rare. I think the only times I did it this year I was pitching to The New York Times.

How Visakan Veerasamy Writes

What’s the best target when writing?

Visakan Veerasamy: Charts out for ribbonfarm.

I do endorse the core thing this is trying to suggest: To explore more and worry about presentation and details less, on most margins. And to know that in a real sense, if you have truly compelling fuckery, you have wiggled your big toe. Hard part is over.

I do not think the core claim itself is correct. Or perhaps we mean different things by resonant and coherent? By coherent, in my lexicon, he means more like ‘well-executed’ or ‘polished’ or something. By resonant, in my lexicon, he means more like ‘on to something central, true and important.’ Whereas to me resonant is a vibe, fully compatible with bullshit, ornate or otherwise.

How Matt Yglesias Writes

Matt Yglesias reflects on four years of Slow Boring. He notes that it pays to be weird, to focus where you have comparative advantage rather than following the news of the week and fighting for a small piece of the biggest pies. He also notes the danger of repeating yourself, which I worry about as well.

How JRR Tolkien Wrote

Thread from 2020 on Tolkien’s path to writing Lord of the Rings. I’ve never done anything remotely like this, which might be some of why I haven’t done fiction.

How Roon Wants Us to Write

Roon calls for the end of all this boring plain language, and I am here for it.

Roon: I love the guy, but I want the post-Goldwater era of utilitarian philosophical writing to be over. Bring back big words and epic prose, and sentences that make sense only at an angle.

Eliezer Yudkowsky: I expect Claude to do a good job of faking your favorite continental styles if you ask, since it requires little logical thinking, only vibes. You can produce and consume it privately in peace, avoiding its negative externalities, and leave the rest of us to our utility.

Roon: Eliezer, you are a good writer who often speaks in parables and communicates through fiction and isn’t afraid of interesting uses of language. You’ve certainly never shied away from verbosity, and that’s exactly what I’m talking about.

Perhaps some day I will learn how to write fiction. My experiences with AI reinforce to me that I really, really don’t know how to do that.

When To Write the Headline

I usually write the headline last. Others disagree.

Luke Kawa: Joe Weisenthal always used to say don’t write a post until you know the headline first. More and more on short posts I find myself thinking “don’t write the post until you know the meme you can post with it first.”

As I said on Twitter, everyone as LessOnline instead gave the advice to not let things be barriers to writing. If you want to be a writer, write more, then edit or toss it out later, but you have to write.

Also, as others pointed out, if you start with the headline every time you are building habits of going for engagement if not clickbait, rather than following curiosity.

Other times, yes, you know exactly what the headline is before you start, because if you know you know.

Do Not Write Self-Deprecating Descriptions of Your Posts

I confirm this is sometimes true (but not always):

Patrick McKenzie: Memo to self and CCing other writers on an FYI basis:

If when announcing a piece you make a self-deprecating comment about it, many people who cite you will give a qualified recommendation of the piece, trying to excuse the flaw that you were joking about.

You think I would understand that ~20 years of writing publicly, but sometimes I cannot help myself from making the self-deprecating comment, and now half of the citations of my best work this year feel they need to disclaim that it is 24k words.

You can safely make the self-deprecating comments within the post itself. That’s fine.

Do Not Write a Book

Don’t write a book. If you do, chances are you’d sell dozens of copies, and earn at most similar quantities of dollars. The odds are very much doubleplusungood. Do you want to go on podcasts this much?

If you must write one anyway, how to sell it? The advice here is that books mostly get sold through recommendations. To get those, Eric Jorgenson’s model is you need three things:

1. Finishable. If they don’t finish it, they won’t recommend it. So tighten it up.

2. Unique OR Excellent. Be the best like no one ever was, or be like no one ever was.

3. Memorable. Have hooks, for when people ask for a book about or for some X.

If you are thinking about writing a book, remember that no one would buy it.

Write Like No One Else is Reading

Michael Dempsey and Ava endorse the principle of writing things down on the internet even if you do not expect anyone to read them.

Michael Dempsey: I loved this thread from Ava.

My entire career is owed to my willingness to write on the Internet.

And that willingness pushed me to write more in my personal life to loved ones.

As long as you recognize that most people will not care, your posts probably will not go viral, but at some point, one person might read something you write and reach out (or will value you including a blue link to your thoughts from many days, weeks, months, or years ago), it's close to zero downside and all upside.

Ava: I’m starting to believe that “write on the Internet, even if no one reads it” is underrated life advice. It does not benefit other people necessarily; it benefits you because the people who do find or like your writing and then reach out are so much more likely to be compatible with you.

It’s also a muscle. I used to have so much anxiety posting anything online, and now I’m just like “lol, if you don’t like it, just click away.” People underestimate the sheer amount of content on the Internet; the chance of someone being angry at you for something is infinitely lower than no one caring.

I think it’s because everyone always sees outrage going viral, and you think “oh, that could be me,” and forget that most people causing outrage are trying very hard to be outrageous. By default, no one cares, or maybe five people care, and maybe some nice strangers like your stuff, and that’s a win.

Also, this really teaches you how to look for content you actually like on the Internet instead of passively receiving what is funneled to you. Some of my favorite Internet experiences have been reading a personal blog linked to someone’s website, never marketed, probably only their friends and family know about it, and it’s just the coolest peek into their mind.

I think the thing I’m trying to say here is “most people could benefit from writing online, whether you should market your writing aggressively is a completely different issue.” I wrote on Tumblr and Facebook and email for many years before Substack, and 20 people read it, and that was great.

I would not broadly recommend “trying to make a living off your writing online,” but that’s very different from “share some writing online.”

What is the number of readers that justifies writing something down? Often the correct answer is zero, even a definite zero. Even if it’s only about those who read it, twenty readers is actually a lot of value to put out there, and a lot of potential connection.

Letting the AI Write For You

Paul Graham predicts that AI will cause the world to divide even more into writes and write-nots. Writing well and learning to write well are both hard, especially because it requires you to think well (and is how you think well), so once AI can do it for us without the need to hire someone or plagiarize, most people won’t learn (and one might add, thanks to AI doing the homework they won’t have to), and increasingly rely on AI to do it for them. Which in turn means those people won’t be thinking well, either, since you need to write to think well.

I think Graham is overstating the extent AI will free people from the pressure to write. Getting AI to write well in turn, and write what you actually want it to write, requires good writing and thinking, and involving AI in your writing OODA loop is often not cheap to do. Yes, more people will choose not to invest in the skill, but I don’t think this takes the pressure off as much as he expects, at least until AI gets a lot better.

There’s also the question of how much we should force people to write anyway, in order to make them think, or be able to think.

As Graham notes, getting rid of the middle ground could be quite bad:

Robin Hanson: But most jobs need real thinking. So either the LLMs will actually do that thinking for them, or workers will continue to write, in order to continue to think. I'd bet on the latter, for decades at least.

Perry Metzger: Why do we still teach kids mathematics, even though at this point, most of the grunt work is done better by computers, even for symbolic manipulation? Because if they’re going to be able to think, they need to practice thinking.

Most jobs don’t require real thinking. Proof: Most people can’t write.

One could argue that many jobs require ‘mid-level’ real thinking, the kind that might be lost, but I think mostly this is not the case. Most tasks and jobs don’t require real thinking at all, as we are talking about it here. Being able to do it? Still highly useful.

On the rare occasions the person can indeed do real thinking, it’s often highly valuable, but the jobs are designed knowing most people can’t and won’t do that.

Being Matt Levine

Gwern asks, why are there so few Matt Levines? His conclusion is that Being Matt Levine requires both that a subject be amenable to a Matt Levine, which most aren’t, and also that there be a Matt Levine covering them, and Matt Levines are both born rather than made and highly rare.

In particular, a Matt Levine has to shout things into the void, over and over, repeating simple explanations time and again, and the subject has to involve many rapidly-resolved example problems to work through, with clear resolutions.

The place where I most epicly fail to be a Matt Levine in this model is my failure to properly address the beginner mindset and keep things simple. My choice to cater to a narrower, more advanced crowd, one that embraces more complexity, means I can’t go wide the way he can. That does seem right.

I could try to change this, but I mostly choose not to. I write too many words as it is.

The Case for Italics

The case for italics. I used to use italics a lot.

Char: “never italicise words to show emphasis! if you’re writing well your reader will know. you don’t need them!” me: oh 𝘳𝘦𝘢𝘭𝘭𝘺? listen up buddy, you will have to pry my emotional support italics from my 𝘤𝘰𝘭𝘥, 𝘥𝘦𝘢𝘥, 𝘧𝘪𝘯𝘨𝘦𝘳𝘴, they are going 𝘯𝘰𝘸𝘩𝘦𝘳𝘦.

Richard White: I'm coming to the conclusion that about 99.9% of all writing "rules" can safely be ignored. As long as your consistent with your application of whatever you're doing, it'll be fine.

Kira: Italics are important for subtlety and I will fight anyone who says otherwise

It’s a great tool to have in your box. What I ultimately found was it is also a crutch that comes with a price. You almost never need italics, and the correct version without italics is easier on the reader.

When I look back on my old writing and see all the italics, I often cringe. Why did I feel the need to do that? Mostly I blame Eliezer Yudkowsky giving me felt permission to do it. About 75% of the time I notice that I can take out the italics and nothing would go wrong. It would be a little less obvious what I’m trying to emphasize, in some senses, but it’s fine. The other 25% of the time, I realize that the italics is load bearing, and if I remove it I will have to reword, so mostly I reword.

Getting Paid

Scott Alexander does his third annual Subscribe Drive. His revenue has leveled off. He had 5,993 paid subscribers in 2023, 5,523 in 2024, and has 5,329 now in 2025. However his unpaid numbers keep going up, from to 78k to 99k to 126k.

I’ve been growing over time, but the ratios do get worse. I doubled my unpaid subscriber count in 2023, and then doubled it again in 2024. But my subscription revenue was only up about 50% in 2023, and only up another 25% in 2024. I of course very much appreciate paid subscriptions, but I am 100% fine, and it is not shocking that my offer of absolutely nothing extra doesn’t get that many takers.

Paywalls are terrible, but how else do you get paid?

Email sent to Rob Henderson: The hypocrisy of the new upper class he proclaims as he sends a paid only email chain…

Cartoons Hate Her: Sort of a different scenario but most people say they think it should be possible to make a living as a writer or artist and still shout “LAME!! PAYWALL!” whenever I attempt to *checks notes* make a living as a writer.

Rob Henderson: Agree with this. Regrettably I’ll be adding more paywalls going forward. But will continue to regularly offer steep discounts and free premium subscriptions.

I am continuously grateful that I can afford to not have a paywall, but others are not so fortunate. You have to pay the bills, even though it is sad that this greatly reduces reach and ability to discuss the resulting posts.

It’s great to be able to write purely to get the message out and not care about clicks. Unfortunately, you do still have to care a little about how people see the message, because it determines how often they and others see future messages. But I am very grateful that, while I face more pressure than Jeff, I face vastly less than most, and don’t have to care at all about traffic for traffic’s sake.

Ideally, we would have more writers who are supported by a patron system, in exchange for having at most a minimal paywall (e.g. I think many would still want a paywall on ability to comment to ensure higher quality or civility, or do what Scott Alexander does and paywall a weird 5% of posts, or do subscriber-questions-only AMAs or what not).

Having Impact

Scott Sumner cites claims that blogging is effective. I sure hope so!

Patrick McKenzie suggests responding to future AIs reading your writing by, among other things, ‘creating more spells’ and techniques that can thereby be associated with you, and then invoked by reference to your name. And to think about how your writing being used as training data causes things to be connected inside LLMs. He also suggests that having your writing outside paywalls can help.

In my case, I’m thinking about structure - the moves between different topics are designed to in various ways ‘make sense to humans’ but I worry about how they might confuse AIs and this could cause confusion in how they understand me and my concepts in particular, including as part of training runs. I already know this is an issue within context windows, AIs are typically very bad at handling these posts as context. One thing this is motivating is more clear breaks and shorter sections than I would otherwise use, and also shorter more thematically tied together posts.

Ben Hoffman does not see a place or method in today’s world for sharing what he sees as high-quality literate discourse, at least given his current methods, although he identifies a few people he could try to usefully engage with more. I consistently find his posts some of the most densely interesting things on the internet and often think a lot about them, even though I very often strongly disagree with what he is saying and also often struggle to even grok his positions, so I’m sad he doesn’t offer us more.

My solution to the problem of ‘no place to do discourse’ is that you can simply do it on Substack on your own, respond to whoever you want to respond to, speak to who you want to speak to and ignore who you want to ignore. I do also crosspost to LessWrong, but I don’t feel any obligation to engage if someone comments in a way that misconstrues what I said.