How To Write an Essay

I think Paul Graham’s style is exactly right for communicating with a broad internet audience, so I’d like to read from him as much to copy his style as to absorb the content.  He thinks really clearly and that clear thinking comes through in his writing.

“Just as inviting people over forces you to clean up your apartment, writing something that other people will read forces you to think well. So it does matter to have an audience. The things I’ve written just for myself are no good. They tend to peter out. When I run into difficulties, I find I conclude with a few vague questions and then drift off to get a cup of tea.” PG

Below are excerpts from Paul Graham’s essays on writing. I need to internalize them. Halp? my commends are in [ brackets ]. Things I think I need to learn are marked with ***


Writing Briefly
I think it’s far more important to write well than most people realize. Writing doesn’t just communicate ideas; it generates them. If you’re bad at writing and don’t like to do it, you’ll miss out on most of the ideas writing would have generated.

As for how to write well, here’s the short version: Write a bad version 1 as fast as you can [workflowy allows me to constantly do this, incrementally, organized]; rewrite it over and over*** [think of re-writing as an attempt to explain it to someone, without simply referencing the post]; cut out everything unnecessary [concision aspirations]; write in a conversational tone*** [illusion of transparency]; develop a nose for bad writing, so you can see and fix it in yours [I spend a lot of time reading the best books I can find]; imitate writers you like [Paul Graham. Steven Pinker. Paul Harding. Daniel Kahneman. Peter Thiel. David Brooks. Nick Cooney. Slate Star Codex. Brain Pickings]; if you can’t get started, tell someone what you plan to write about, then write down what you said [I need people to talk to who have at least my expected knowledge assumptions both before and after I write something]; expect 80% of the ideas in an essay to happen after you start writing it, and 50% of those you start with to be wrong; be confident enough to cut; have friends you trust read your stuff and tell you which bits are confusing or drag; don’t (always) make detailed outlines; mull ideas over for a few days before writing; carry a small notebook or scrap paper with you; start writing when you think of the first sentence; if a deadline forces you to start before that, just say the most important sentence first [i don’t like deadlines]; write about stuff you like; don’t try to sound impressive [good sales is invisible]; don’t hesitate to change the topic on the fly***[I narrow frame]; use footnotes to contain digressions; use anaphora to knit sentences together; read your essays out loud to see (a) where you stumble over awkward phrases and (b) which bits are boring (the paragraphs you dread reading) [I’m okay having boring bits. Not all my writing are essays. some are about things I want to learn, and sometimes learning is boring]; try to tell the reader something new and useful; work in fairly big quanta of time; when you restart, begin by rereading what you have so far; when you finish, leave yourself something easy to start with; accumulate notes for topics you plan to cover at the bottom of the file; don’t feel obliged to cover any of them; write for a reader who won’t read the essay as carefully as you do, just as pop songs are designed to sound ok on crappy car radios***; if you say anything mistaken, fix it immediately [I prefer having “edit” notes in my workflowy. I procrastinate the edit until I have sufficient motivation. do easy.”]; ask friends which sentence you’ll regret most***; go back and tone down harsh remarks; publish stuff online, because an audience makes you write more, and thus generate more ideas; print out drafts instead of just looking at them on the screen***; use simple, germanic words; learn to distinguish surprises from digressions***; learn to recognize the approach of an ending, and when one appears, grab it.


Age of The Essay
Defending a position may be a necessary evil in a legal dispute, but it’s not the best way to get at the truth, as I think lawyers would be the first to admit. It’s not just that you miss subtleties this way. The real problem is that you can’t change the question.

Good writing should be convincing because you got the right answers, not because you did a good job of arguing.

An essay doesn’t begin with a statement, but with a question. In a real essay, you don’t take a position and defend it. You notice a door that’s ajar, and you open it and walk in to see what’s inside.

Expressing ideas helps to form them. Indeed, helps is far too weak a word. Most of what ends up in my essays I only thought of when I sat down to write them. That’s why I write them.

In the things you write in school you are, in theory, merely explaining yourself to the reader. In a real essay you’re writing for yourself. You’re thinking out loud.

Just as inviting people over forces you to clean up your apartment, writing something that other people will read forces you to think well [goal: think clearly]. So it does matter to have an audience. The things I’ve written just for myself are no good. They tend to peter out. When I run into difficulties, I find I conclude with a few vague questions and then drift off to get a cup of tea. Many published essays peter out in the same way. Particularly the sort written by the staff writers of newsmagazines.

Questions aren’t enough. An essay has to come up with answers [spend more time thinking of the answers to interesting questions ***]. They don’t always, of course. Sometimes you start with a promising question and get nowhere. But those you don’t publish [aka they sit in the workflowy]. Those are like experiments that get inconclusive results [writing essays is a form of science]. An essay you publish ought to tell the reader something he didn’t already know.

But what you tell him doesn’t matter, so long as it’s interesting. I’m sometimes accused of meandering. In defend-a-position writing that would be a flaw. There you’re not concerned with truth. You already know where you’re going, and you want to go straight there, blustering through obstacles, and hand-waving your way across swampy ground [rationalization]. But that’s not what you’re trying to do in an essay. An essay is supposed to be a search for truth. It would be suspicious if it didn’t meander. [I think about half my posts are essays, and the other half more “traditional”, i.e. explicitly goal oriented].

The Meander (aka Menderes) is a river in Turkey. As you might expect, it winds all over the place. But it doesn’t do this out of frivolity. The path it has discovered is the most economical route to the sea.

The river’s algorithm is simple. At each step, flow down [one must first generate all possible options before flowing down***]. For the essayist this translates to: flow interesting. Of all the places to go next, choose the most interesting. One can’t have quite as little foresight as a river. I always know generally what I want to write about. But not the specific conclusions I want to reach [write down, and then let go of, conclusions when i have them***]; from paragraph to paragraph I let the ideas take their course.

This doesn’t always work. Sometimes, like a river, one runs up against a wall. Then I do the same thing the river does: backtrack. At one point in this essay I found that after following a certain thread I ran out of ideas. I had to go back seven paragraphs and start over in another direction. [getting over sunk costs is very difficult***]

Fundamentally an essay is a train of thought– but a cleaned-up train of thought, as dialogue is cleaned-up conversation. Real thought, like real conversation, is full of false starts. It would be exhausting to read. You need to cut and fill to emphasize the central thread, like an illustrator inking over a pencil drawing. But don’t change so much that you lose the spontaneity of the original.*** [this is what I have only begun doing with the “Key Points” doc]

So what’s interesting? For me, interesting means surprise. Interfaces, as Geoffrey James has said, should follow the principle of least astonishment. A button that looks like it will make a machine stop should make it stop, not speed up. Essays should do the opposite. Essays should aim for maximum surprise.*** [maximize surprise. I like that.]

Surprises are things that you not only didn’t know, but that contradict things you thought you knew. And so they’re the most valuable sort of fact you can get. They’re like a food that’s not merely healthy, but counteracts the unhealthy effects of things you’ve already eaten.

How do you find surprises? Well, therein lies half the work of essay writing. (The other half is expressing yourself well.) The trick is to use yourself as a proxy for the reader. You should only write about things you’ve thought about a lot. And anything you come across that surprises you, who’ve thought about the topic a lot, will probably surprise most readers.

So if you want to write essays, you need two ingredients: a few topics you’ve thought about a lot, and some ability to ferret out the unexpected.

Collecting surprises is a similar process. The more anomalies you’ve seen, the more easily you’ll notice new ones. Which means, oddly enough, that as you grow older, life should become more and more surprising. When I was a kid, I used to think adults had it all figured out. I had it backwards. Kids are the ones who have it all figured out. They’re just mistaken.

When it comes to surprises, the rich get richer. But (as with wealth) there may be habits of mind that will help the process along. It’s good to have a habit of asking questions, especially questions beginning with Why. But not in the random way that three year olds ask why. There are an infinite number of questions. How do you find the fruitful ones?

I find it especially useful to ask why about things that seem wrong. For example, why should there be a connection between humor and misfortune? Why do we find it funny when a character, even one we like, slips on a banana peel? There’s a whole essay’s worth of surprises there for sure.

If you want to notice things that seem wrong, you’ll find a degree of skepticism helpful. I take it as an axiom that we’re only achieving 1% of what we could. This helps counteract the rule that gets beaten into our heads as children: that things are the way they are because that is how things have to be. For example, everyone I’ve talked to while writing this essay felt the same about English classes– that the whole process seemed pointless. But none of us had the balls at the time to hypothesize that it was, in fact, all a mistake. We all thought there was just something we weren’t getting.

I have a hunch you want to pay attention not just to things that seem wrong, but things that seem wrong in a humorous way. I’m always pleased when I see someone laugh as they read a draft of an essay. But why should I be? I’m aiming for good ideas. Why should good ideas be funny? The connection may be surprise. Surprises make us laugh, and surprises are what one wants to deliver.

People trying to be cool will find themselves at a disadvantage when collecting surprises. To be surprised is to be mistaken.

One of the keys to coolness is to avoid situations where inexperience may make you look foolish. If you want to find surprises you should do the opposite. Study lots of different things, because some of the most interesting surprises are unexpected connections between different fields. For example, jam, bacon, pickles, and cheese, which are among the most pleasing of foods, were all originally intended as methods of preservation. And so were books and paintings.

Above all, make a habit of paying attention to things you’re not supposed to, either because they’re “inappropriate,” or not important, or not what you’re supposed to be working on. If you’re curious about something, trust your instincts. Follow the threads that attract your attention. If there’s something you’re really interested in, you’ll find they have an uncanny way of leading back to it anyway, just as the conversation of people who are especially proud of something always tends to lead back to it.

For example, I’ve always been fascinated by comb-overs, especially the extreme sort that make a man look as if he’s wearing a beret made of his own hair. Surely this is a lowly sort of thing to be interested in– the sort of superficial quizzing best left to teenage girls. And yet there is something underneath. The key question, I realized, is how does the comber-over not see how odd he looks? And the answer is that he got to look that way incrementally. What began as combing his hair a little carefully over a thin patch has gradually, over 20 years, grown into a monstrosity. Gradualness is very powerful. And that power can be used for constructive purposes too: just as you can trick yourself into looking like a freak, you can trick yourself into creating something so grand that you would never have dared to plan such a thing. Indeed, this is just how most good software gets created. You start by writing a stripped-down kernel (how hard can it be?) and gradually it grows into a complete operating system. Hence the next leap: could you do the same thing in painting, or in a novel?

See what you can extract from a frivolous question? If there’s one piece of advice I would give about writing essays, it would be: don’t do as you’re told. Don’t believe what you’re supposed to. Don’t write the essay readers expect; one learns nothing from what one expects. And don’t write the way they taught you to in school.

there are a lot of things insiders can’t say precisely because they’re insiders.

The Internet is changing that. Anyone can publish an essay on the Web, and it gets judged, as any writing should, by what it says, not who wrote it. Who are you to write about x? You are whatever you wrote.

Popular magazines made the period between the spread of literacy and the arrival of TV the golden age of the short story. The Web may well make this the golden age of the essay. And that’s certainly not something I realized when I started writing this.


How To Do Philosophy

The goal Aristotle announces in the Metaphysics seems one worth pursuing: to discover the most general truths. That sounds good. But instead of trying to discover them because they’re useless, let’s try to discover them because they’re useful.

Instead of trying to answer the question: What are the most general truths? let’s try to answer the question: Of all the useful things we can say, which are the most general? [this knowledge distribution (wisdom vs intelligence) is impact oriented because it tries to answer this question]

The test of utility is whether we cause people who read what we’ve written to do anything differently afterward. Knowing we have to give definite (if implicit) advice will keep us from straying beyond the resolution of the words we’re using.

the usefulness test will tend to produce results that annoy people: there’s no use in telling people things they already believe, and people are often upset to be told things they don’t.

These seem to me what philosophy should look like: quite general observations that would cause someone who understood them to do something differently.

It gives people with good intentions a new roadmap into abstraction. And they may thereby produce things that make the writing of the people with bad intentions look bad by comparison.

One drawback of this approach is that it won’t produce the sort of writing that gets you tenure. And not just because it’s not currently the fashion. In order to get tenure in any field you must not arrive at conclusions that members of tenure committees can disagree with.

Words: The real lesson here is that the concepts we use in everyday life are fuzzy, and break down if pushed too hard. Even a concept as dear to us as I. It took me a while to grasp this, but when I did it was fairly sudden, like someone in the nineteenth century grasping evolution and realizing the story of creation they’d been told as a child was all wrong. [2] Outside of math there’s a limit to how far you can push words; in fact, it would not be a bad definition of math to call it the study of terms that have precise meanings. Everyday words are inherently imprecise. They work well enough in everyday life that you don’t notice. Words seem to work, just as Newtonian physics seems to. But you can always make them break if you push them far enough.

I would say that this has been, unfortunately for philosophy, the central fact of philosophy. Most philosophical debates are not merely afflicted by but driven by confusions over words. Do we have free will? Depends what you mean by “free.” Do abstract ideas exist? Depends what you mean by “exist.”

Historyancient philosophers were in effect arguing about artifacts (i.e. abstractions) induced by sampling at too low a resolution. Surely I’m not claiming that ideas have to have practical applications to be interesting? No, they may not have to. Hardy’s boast that number theory had no use whatsoever wouldn’t disqualify it. But he turned out to be mistaken. In fact, it’s suspiciously hard to find a field of math that truly has no practical use. And Aristotle’s explanation of the ultimate goal of philosophy in Book A of the Metaphysics implies that philosophy should be useful too.

Theoretical Knowledgean ordinary worker builds things a certain way out of habit; a master craftsman can do more because he grasps the underlying principles. The trend is clear: the more general the knowledge, the more admirable it is. But then he makes a mistake—possibly the most important mistake in the history of philosophy. He [Aristotle] has noticed that theoretical knowledge is often acquired for its own sake, out of curiosity, rather than for any practical need. So he proposes there are two kinds of theoretical knowledge: some that’s useful in practical matters and some that isn’t. Since people interested in the latter are interested in it for its own sake, it must be more noble. So he sets as his goal in the Metaphysics the exploration of knowledge that has no practical use. Which means no alarms go off when he takes on grand but vaguely understood questions and ends up getting lost in a sea of words.

His mistake was to confuse motive and result. Certainly, people who want a deep understanding of something are often driven by curiosity rather than any practical need. But that doesn’t mean what they end up learning is useless. It’s very valuable in practice to have a deep understanding of what you’re doing; even if you’re never called on to solve advanced problems, you can see shortcuts in the solution of simple ones, and your knowledge won’t break down in edge cases, as it would if you were relying on formulas you didn’t understand. Knowledge is power. That’s what makes theoretical knowledge prestigious. It’s also what causes smart people to be curious about certain things and not others; our DNA is not so disinterested as we might think.

So while ideas don’t have to have immediate practical applications to be interesting, the kinds of things we find interesting will surprisingly often turn out to have practical applications.

why philosophy is attractive: If you write in an unclear way about big ideas, you produce something that seems tantalizingly attractive to inexperienced but intellectually ambitious students. Till one knows better, it’s hard to distinguish something that’s hard to understand because the writer was unclear in his own mind from something like a mathematical proof that’s hard to understand because the ideas it represents are hard to understand. To someone who hasn’t learned the difference, traditional philosophy seems extremely attractive: as hard (and therefore impressive) as math, yet broader in scope. That was what lured me in as a high school student.

Abstract-sounding nonsense seems to be most attractive when it’s aligned with some axe the audience already has to grind. If this is so we should find it’s most popular with groups that are (or feel) weak. The powerful don’t need its reassurance.

Hitherto the people attracted to philosophy have been mostly those who loved the big generalizations, which were all wrong, so that few people with exact minds have taken up the subject.

There’s a market for writing that sounds impressive and can’t be disproven.

Civilization always seems old, because it’s always the oldest it’s ever been. The only way to say whether something is really old or not is by looking at structural evidence, and structurally philosophy is young; it’s still reeling from the unexpected breakdown of words.


The illusion of transparency: why no one understands you

“In hindsight bias, people who know the outcome of a situation believe the outcome should have been easy to predict in advance.  Knowing the outcome, we reinterpret the situation in light of that outcome.  Even when warned, we can’t de-interpret to empathize with someone who doesn’t know what we know.”

“illusion of transparency:  We always know what we mean by our words, and so we expect others to know it too.  Reading our own writing, the intended interpretation falls easily into place, guided by our knowledge of what we really meant.  It’s hard to empathize with someone who must interpret blindly, guided only by the words.”

“Be not too quick to blame those who misunderstand your perfectly clear sentences, spoken or written.  Chances are, your words are more ambiguous than you think.”

Double illusion of transparency
“First, I assumed that my words meant what I intended them to mean – that my listeners heard my intentions as though they were transparent.  Second, when someone repeated back my sentences using slightly different word orderings, I assumed that what I heard was what they had intended to say.  As if all words were transparent windows into thought, in both directions.”

“words, like all other useful forms of thought, are secretly a disguised form of Bayesian inference”


Explainers tend to shoot high, when they should aim low

General readers expect short inference distances. That is, explanations that only require one or two additional pieces of information to convey the new idea.

“A clear argument has to lay out an inferential pathway, starting from what the audience already knows or accepts.  If you don’t recurse far enough, you’re just talking to yourself … we tend to enormously underestimate the effort required to properly explain things … This is not because your audience is more stupid than you think, but because your words are far less helpful than you think.  You’re way way overshooting the target.  Aim several major gradations lower, and you may hit your mark.”

A vague formula for an inferential pathway (John Maxwell):

  • Find an idea that you think your reader already understands and is an important prerequisite of what you are trying to say.
  • Write a simple one-sentence summary of the idea, identifying it by whatever term is commonly used for it.  Include a link somewhere in the sentence for readers who *aren’t* already familiar with the idea.
  • In the next sentence, make some kind of straightforward extension of the idea.  For example, connect it to some other idea, identify a situation where it’s flawed, etc.  Make it so these sentences are totally comprehensible and stand on their own.
  • Keep doing that until you’ve gotten where you need to go.
  • Repeat from the first step if you need to introduce a new idea.
  • Connect all these threads.  Figure out how the ideas add up, contrast, etc.
  • Read your essay aloud repeatedly until it comes across as smooth, conversational, and fluid.


Be Specific!
This is one of the most common bits of nonfiction writing advice I dispense:  “Open with the concrete example, not the abstract explanation!” (concrete-abstract writing pattern. i.e. move down the lattice of abstraction before moving up). The skill of Being Specific is the skill of understanding how to navigate the lattice of abstraction.

Something is sufficiently concrete you can potentially see something and say “Oh, I guess the hypothesis was wrong”; you must be able to have an experience which the concretized – rendered near-to-experience –  statement constrains, and which falsifies the theory if the experience is out-of-bounds.

criterion for specific enoughMy hypothesis about what it means to be “specific enough” or “concrete enough” is that the picture painted is detailed enough to use in model-checking whatever points are being debated.

model checking vs deductionCorrespondingly, in logical inference, there’s a distinction between model-checking and deduction.  Suppose you want to know whether it’s true that all positive integers less than 5, when multiplied by 7, are less than 50.  If you prove the general truth that all integers less than 5, times 7, are less than 35, by manipulating the axioms of multiplication and inequality, that’s deduction.  If you notice that the only positive integers less than 5 are just {1, 2, 3, 4} and enumerate their products {7, 14, 21, 28}, which are all less than 50, that’s model-checking.

Therefor, something is specific enough if a use case’s resolution allows one to model check against answers to necessary questions. For example, consider Paul Graham has some questions to ask a start-up:

  • How much would I pay for this product?
  • Is this startup exciting enough that I would tweet about using it?
  • How much resources will it take to develop these features further?

PG doesn’t want you to say, “$50, yes, and twenty engineer-months”.  He wants a sufficiently specific picture of (a customer using) your product that he can arrive at his own answers by model-checking.

Five-second-level skill:

  • Trigger:  Recognizing when your words or thoughts are too abstract.
  • Action:  Moving downward in the abstraction lattice, or moving nearer to sense input or motor output; being able to render your thoughts more specific or more concrete.

abstract words can avoid emotion: George Orwell:  “Defenceless villages are bombarded from the air, the inhabitants driven out into the countryside, the cattle machine-gunned, the huts set on fire with incendiary bullets: this is called pacification.”  Or contrast “Humanity is awful, it’d be better for the planet if we all died” to “Everyone including my little sister is awful, we’d be better off if everyone died including her.”  To feel sympathy, we need enough concrete detail that our emotions can model-check the picture and be activated.

Being specific helps notice and call bluffs, should you be mischievously inclined.

Visualizing specific examples often improves quality of thought in general – we’re often smarter when we’re using both model-checking and deduction, visualizing a picture of what we’re supposed to be reasoning about, constantly checking our deductive steps against some specific model those deductions are supposed to be true about


Miscellaneous Notes:

  • Syllogisms
    • It might be useful to adopt a kind of formal logic approach: explicitly state a set of premises, derivations, and conclusions.  For example, try to structure your thinking using syllogisms:  
    • Syllogisms aren’t for proving things so much as giving the reader a map of the argument–a scaffold for its internal structure.  And the premises of a syllogism can, in turn, be other arguments with their own internal structure.
  • lean hard on related concepts your reader may already be familiar with
  • ask myself: how many other possible interpretations fit my words?
  • is-ought distinction
    • description > explanation
    • “there seems to be a significant difference between descriptive statements (about what is) and prescriptive or normative statements (about what ought to be), and that it is not obvious how one can coherently move from descriptive statements to prescriptive ones” Wikipedia
  • Where fuzzy thinking is motivated, overly abstract thinking is motivated
  • search for the historical causes of your thoughts, rather than their justifications.
  • What are allowable implicit assumptions if writing for the 10th percentile of EAs?
  • “Make things as simple as possible, but not simpler.”

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