Some of Scott Alexander's Writing Tricks

The success of Scott Alexander (AKA Scott Siskind) seems unlikely. He’s done everything we’re told you shouldn’t do when writing on the internet. His essays are frighteningly long. His language is not simple. And he doesn’t have a personal brand, exactly. He does cluster around a few subjects repeatedly—psychiatry and political philosophy, for example—but he also does whatever the fuck he wants to. When his whim dictates, he’ll pen surreal stories about psychedelic cacti, dole out advice to Republicans, or tackle tricky philosophical questions with comic dialogues.

And yet.

He’s probably one of the most respected bloggers out there. He pulls a generous Substack salary in his new incarnation, Astral Codex Ten. He’s read by influential people from tech, business, and the media. And there's basically a whole subculture united around enjoying his work, filled with people who occasionally call him, I’m told, “our rightful caliph.”

The fact that he is all these things, while being verbose, complex, and scattered, pretty much definitionally means he’s an effective writer, whether you like him or not. Also, about 1/4 of my clients say he’s a writer who inspires them, so I’m professionally obligated to think about what makes him so popular.

Part of it is a lot of little prose tics that his readers find endearing. For example, he frequently engages in DFW-ish mixed diction, using phrases like ‘immamentize the eschaton’ and ‘okay whatever’ quite close together. Such tics are easy to notice and easy to pick up, if you feel like emulating him. Generally I’d recommend trying to emulate prose you like, even just as an exercise—over time, you absorb little tools and tics into your own voice, and, suddenly, one day, your voice is really interesting.

But prose tics alone won’t get a huge audience to read your 5,000 word essay. What will pull your readers in, and keep them there, is storytelling, pacing, and structure—and this is where Scott’s real gifts lie. Here are a few of his most replicable tactics in that area.

Evocative Analogies

Most brainy essays are trying to suck. That’s because most people aren’t terribly moved by abstract concepts and niche information. It’s just not that emotionally satisfying to hear intellectual trivia, even if it sparks a short-term oh-that’s-a-cool-fact reaction.

For example. Let’s say I wrote an essay about Russian pharmaceuticals that opened, “so, in Russia, they’ve got different drugs that we don’t have here,” and then proceeded to a list of examples. That would be pretty unmemorable for readers who don’t care about pharmaceuticals.

Scott knows this. So, when he writes an essay about weird Russian drugs, he doesn’t do what I did. Here’s how it opens.

Imagine if a chemist told you offhandedly that the Russians had different chemical elements than we did.

Here in America, we use elements like lithium and silicon and bismuth. We have figured out lots of neat compounds we can make with these elements. We’ve also figured out useful technological applications. Lithium makes batteries. Silicon makes computer chips. Bismuth makes pretty gifs you can post on Tumblr.

The Russians don’t use any of these. They have their own Russian elements on their own Russian periodic table, with long Russian names you can’t pronounce. Apparently some of these also have useful technological applications. One of them is a room temperature superconductor. Another improves the efficiency of dirigibles by 500% for some reason.

If a chemist told you this, you would think they were crazy. Science, you would say, is science everywhere. You can’t have one set of elements in Russia and another in the US, everyone would work together and compare notes. At the very least one side would have the common decency to at least steal from the other. No way anything like this could possibly go on.

But as far as I can tell this is exactly the state of modern psychopharmacology.

This physics analogy does what good poetry does—it makes reality strange. By leading us to see the situation in a different light, he forces us to consider it more thoroughly. He transmits his imagination to the reader. (Also, the dirigibles bit is a clever non-sequitur that keeps the mood light and casual, signaling to the reader that they’re not at a boring lecture.)

Scott does this kind of thing All. The. Time. Like when he explains intellectual fashion with a fable about toga fashions. Or when he compares social justice infighting to whale cancer. Oh, and there’s this gigantic post where he identifies a mechanism that could destroy society and calls it Moloch, after a monster in a Ginsberg poem.

This is something you can absolutely do. The danger, of course, is coming up with a fanciful analogy that doesn’t lend any poetry to the situation—occasionally you see this on LessWrong from Scott imitators. There is an art here that can be screwed up. But it’s an art worth practicing.

Real-Time Dialectics

Intellectual positions, on their own, are kind of inert. Maybe Heidegger tells us that we should ground our examinations of reality in the experience of the sentient being. Sure. Sounds nice. Mildly provocative. Time to wander off and watch YouTube.

On the other hand, philosophical ideas get more exciting when they cause friction—when one idea smashes headlong into another. This is why debates are usually more fun than philosophy books, even though they’re often less informative. (And why philosophy books are most fun when they’re written in a scrappy, argumentative matter, à la David Bentley Hart.)

Scott understands this. So, sometimes, he’ll structure part of an essay as a war between different, related sentiments. Only, instead of engaging in this war with someone else, he plays out the battle against himself, within the essay. This is a super, super cool move, and I’ve never seen anyone else do it so well.

He does this in one of his most-loved posts, I Can Tolerate Anything Except the Outgroup

For awhile, the essay masquerades as a self-deprecating takedown of liberal sensibilities. Scott identifies two tribes in America, the Red Tribe and the Blue Tribe. (Basically, lower-class Republicans and Democrat intelligentsia, respectively.) He identifies himself as the latter, and then makes fun of his own tribe. He points out that they constantly talk about how tolerant they are, but they’re actually totally intolerant of one group of people—their immediate outgroup, the Red Tribe. They criticize the Red Tribe while disguising it as self-criticism, by saying they’re criticizing “white people” or “Americans.”

Spending your entire life insulting the other tribe and talking about how terrible they are makes you look, well, tribalistic. It is definitely not high class. So when members of the Blue Tribe decide to dedicate their entire life to yelling about how terrible the Red Tribe is, they make sure that instead of saying “the Red Tribe”, they say “America”, or “white people”, or “straight white men”. That way it’s humble self-criticism. They are so interested in justice that they are willing to critique their own beloved side, much as it pains them to do so. 

This is reasonable enough, if a little smug and oversimplified. But then he pulls back the curtain, in the next part, which starts like this, after a section break: 

This essay is bad and I should feel bad.

I should feel bad because I made exactly the mistake I am trying to warn everyone else about, and it wasn’t until I was almost done that I noticed.

How virtuous, how noble I must be! Never stooping to engage in petty tribal conflict like that silly Red Tribe, but always nobly criticizing my own tribe and striving to make it better.

Yeah. Once I’ve written a ten thousand word essay savagely attacking the Blue Tribe, either I’m a very special person or they’re my outgroup. And I’m not that special.

Just as you can pull a fast one and look humbly self-critical if you make your audience assume there’s just one American culture, so maybe you can trick people by assuming there’s only one Blue Tribe.

He goes on to say that, basically, not a member of the Blue Tribe, exactly— he’s a libertarianish weirdo, a member of what he calls the Grey Tribe. So, in reality, he’s an elite mocking the outgroup, just like the outgroup he’s lampooning. So, over the course of the essay, he’s gone from:

  1. Liberals are uniquely fond of cloaking their condescension towards other tribes. Their tolerance is fake—they only tolerate when it doesn't actually matter.


  1. Everyone, including me, is capable of being extremely self-righteous and tribalistic, while masking it intellectually. Tolerance of outgroups is extremely hard to do in a non-fake way, no matter who you are.

When Scott makes moves like this, it gives his ideas life by making them characters in a story. Instead of the essay merely being an explanation, which is what most essays end up being, it’s a documentation of transformation, which is what most good stories are.

Evocative Anecdotes

Most people, and thus most readers, are primed to absorb socially anchored information. This is a fancy way of saying that stories about people are more exciting than abstract principles—or, at least, that abstract principles can be nicely bolstered by anecdotes. So, if you’re trying to explain a principle, it would behoove you, dear writer, to come up with an illustrative real example.

This can be an evil technique. For example, Malcolm Gladwell is basically the dark priest of dubious anecdotal illustration. He’ll skillfully recount some fun story about a firefighter, tack on a misrepresented study, and then use this salad to advance a specious grand narrative about life in general. 

Scott uses stories in a less dishonest way. Typically, his stories illustrate a disposition, or illuminate a point of view, but he doesn’t generalize them unreasonably. One shining example comes in a a rather heady pro-transgender post from 2014. The post is a rebuttal to the idea that you shouldn’t treat gender dysphoria because it’s a ‘mental disorder’ or a ‘delusion.’ His response is that what psychiatrists should do is make people happy—it truly doesn’t matter whether you think that transgender people Really Are one gender or another in some essential way.

He bolsters this opinion with a wonderful story:

…I think of the Hair Dryer Incident.

The Hair Dryer Incident was probably the biggest dispute I’ve seen in the mental hospital where I work. Most of the time all the psychiatrists get along and have pretty much the same opinion about important things, but people were at each other’s throats about the Hair Dryer Incident.

Basically, this one obsessive compulsive woman would drive to work every morning and worry she had left the hair dryer on and it was going to burn down her house. So she’d drive back home to check that the hair dryer was off, then drive back to work, then worry that maybe she hadn’t really checked well enough, then drive back, and so on ten or twenty times a day.

It’s a pretty typical case of obsessive-compulsive disorder, but it was really interfering with her life. She worked some high-powered job – I think a lawyer – and she was constantly late to everything because of this driving back and forth, to the point where her career was in a downspin and she thought she would have to quit and go on disability.

So she came to my hospital and was seen by a colleague of mine, who told her “Hey, have you thought about just bringing the hair dryer with you?”

And it worked.

She would be driving to work in the morning, and she’d start worrying she’d left the hair dryer on and it was going to burn down her house, and so she’d look at the seat next to her, and there would be the hair dryer, right there. And she only had the one hair dryer, which was now accounted for. So she would let out a sigh of relief and keep driving to work.

And approximately half the psychiatrists at my hospital thought this was absolutely scandalous, and This Is Not How One Treats Obsessive Compulsive Disorder, and what if it got out to the broader psychiatric community that instead of giving all of these high-tech medications and sophisticated therapies we were just telling people to put their hair dryers on the front seat of their car?

But I think the guy deserved a medal. Here’s someone who was totally untreatable by the normal methods, with a debilitating condition, and a drop-dead simple intervention that nobody else had thought of gave her her life back.

The primary thing in psychiatry is to help the patient, whatever the means. Someone can concern-troll that the hair dryer technique leaves something to be desired in that it might have prevented the patient from seeking a more thorough cure that would prevent her from having to bring the hair dryer with her. But compared to the alternative of “nothing else works” it seems clearly superior.

And that’s the position from which I think a psychiatrist should approach gender dysphoria, too.

Fun, right?

Much of the time, people who write about ideas are inspired to do so by some anecdote they encounter in real life. Sometimes, in an effort to write ‘cleanly’ and ‘clearly’, they leave those anecdotes out, and just focus on the idea. But often, they’re hamstringing themselves. Being evocative is being clear, in that it aids absorption. Try leaving the human side in.

The General Principle

There’s a general principle here: Scott uses tools of storytelling and evocation while talking about incredibly nerdy, abstract stuff. He adds depth and texture to the theoretical by grounding it in reality, depicts ideas as living creatures by showing their lifecycles, and finds analogies and parallels that make his ideas more palpable and interesting.

I mentioned earlier that lots of clients come to me who say that they love Scott’s writing, and that he’s a person who they want to emulate. Funnily enough, these clients often talk, also, about how they’ve heard that you should write translucently, avoiding theatre and elaborate metaphor, while keeping the word count as low as possible. Somehow they’ve absorbed the meme that writing well is primarily about clarity, clarity, clarity, and concision, concision, concision. Do the job and go home. Fancy is bad.

To this I usually say something like, “uh, but, you love Scott’s writing, he’s, like, your favorite—have you read Scott’s writing?”