February 2020

What should an essay be? Many people would say persuasive. That’s
what a lot of us were taught essays should be. But I think we can
aim for something more ambitious: that an essay should be useful.

To start with, that means it should be correct. But it’s not enough
merely to be correct. It’s easy to make a statement correct by
making it vague. That’s a common flaw in academic writing, for
example. If you know nothing at all about an issue, you can’t go
wrong by saying that the issue is a complex one, that there are
many factors to be considered, that it’s a mistake to take too
simplistic a view of it, and so on.

Though no doubt correct, such statements tell the reader nothing.
Useful writing makes claims that are as strong as they can be made
without becoming false.

For example, it’s more useful to say that Pike’s Peak is near the
middle of Colorado than merely somewhere in Colorado. But if I say
it’s in the exact middle of Colorado, I’ve now gone too far, because
it’s a bit east of the middle.

Precision and correctness are like opposing forces. It’s easy to
satisfy one if you ignore the other. The converse of vaporous
academic writing is the bold, but false, rhetoric of demagogues.
Useful writing is bold, but true.

It’s also two other things: it tells people something important,
and that at least some of them didn’t already know.

Telling people something they didn’t know doesn’t always mean
surprising them. Sometimes it means telling them something they
knew unconsciously but had never put into words. In fact those may
be the more valuable insights, because they tend to be more
fundamental.

Let’s put them all together. Useful writing tells people something
true and important that they didn’t already know, and tells them
as unequivocally as possible.

Notice these are all a matter of degree. For example, you can’t
expect an idea to be novel to everyone. Any insight that you have
will probably have already been had by at least one of the world’s
7 billion people. But it’s sufficient if an idea is novel to a lot
of readers.

Ditto for correctness, importance, and strength. In effect the four
components are like numbers you can multiply together to get a score
for usefulness. Which I realize is almost awkwardly reductive, but
nonetheless true.

_____

How can you ensure that the things you say are true and novel and
important? Believe it or not, there is a trick for doing this. I
learned it from my friend Robert Morris, who has a horror of saying
anything dumb. His trick is not to say anything unless he’s sure
it’s worth hearing. This makes it hard to get opinions out of him,
but when you do, they’re usually right.

Translated into essay writing, what this means is that if you write
a bad sentence, you don’t publish it. You delete it and try again.
Often you abandon whole branches of four or five paragraphs. Sometimes
a whole essay.

You can’t ensure that every idea you have is good, but you can
ensure that every one you publish is, by simply not publishing the
ones that aren’t.

In the sciences, this is called publication bias, and is considered
bad. When some hypothesis you’re exploring gets inconclusive results,
you’re supposed to tell people about that too. But with essay
writing, publication bias is the way to go.

My strategy is loose, then tight. I write the first draft of an
essay fast, trying out all kinds of ideas. Then I spend days rewriting
it very carefully.

I’ve never tried to count how many times I proofread essays, but
I’m sure there are sentences I’ve read 100 times before publishing
them. When I proofread an essay, there are usually passages that
stick out in an annoying way, sometimes because they’re clumsily
written, and sometimes because I’m not sure they’re true. The
annoyance starts out unconscious, but after the tenth reading or
so I’m saying “Ugh, that part” each time I hit it. They become like
briars that catch your sleeve as you walk past. Usually I won’t
publish an essay till they’re all gone — till I can read through
the whole thing without the feeling of anything catching.

I’ll sometimes let through a sentence that seems clumsy, if I can’t
think of a way to rephrase it, but I will never knowingly let through
one that doesn’t seem correct. You never have to. If a sentence
doesn’t seem right, all you have to do is ask why it doesn’t, and
you’ve usually got the replacement right there in your head.

This is where essayists have an advantage over journalists. You
don’t have a deadline. You can work for as long on an essay as you
need to get it right. You don’t have to publish the essay at all,
if you can’t get it right. Mistakes seem to lose courage in the
face of an enemy with unlimited resources. Or that’s what it feels
like. What’s really going on is that you have different expectations
for yourself. You’re like a parent saying to a child “we can sit
here all night till you eat your vegetables.” Except you’re the
child too.

I’m not saying no mistake gets through. For example, I added condition
(c) in “A Way to Detect Bias”
after readers pointed out that I’d
omitted it. But in practice you can catch nearly all of them.

There’s a trick for getting importance too. It’s like the trick I
suggest to young founders for getting startup ideas: to make something
you yourself want. You can use yourself as a proxy for the reader.
The reader is not completely unlike you, so if you write about
topics that seem important to you, they’ll probably seem important
to a significant number of readers as well.

Importance has two factors. It’s the number of people something
matters to, times how much it matters to them. Which means of course
that it’s not a rectangle, but a sort of ragged comb, like a Riemann
sum.

The way to get novelty is to write about topics you’ve thought about
a lot. Then you can use yourself as a proxy for the reader in this
department too. Anything you notice that surprises you, who’ve
thought about the topic a lot, will probably also surprise a
significant number of readers. And here, as with correctness and
importance, you can use the Morris technique to ensure that you
will. If you don’t learn anything from writing an essay, don’t
publish it.

You need humility to measure novelty, because acknowledging the
novelty of an idea means acknowledging your previous ignorance of
it. Confidence and humility are often seen as opposites, but in
this case, as in many others, confidence helps you to be humble.
If you know you’re an expert on some topic, you can freely admit
when you learn something you didn’t know, because you can be confident
that most other people wouldn’t know it either.

The fourth component of useful writing, strength, comes from two
things: thinking well, and the skillful use of qualification. These
two counterbalance each other, like the accelerator and clutch in
a car with a manual transmission. As you try to refine the expression
of an idea, you adjust the qualification accordingly. Something
you’re sure of, you can state baldly with no qualification at all,
as I did the four components of useful writing. Whereas points that
seem dubious have to be held at arm’s length with perhapses.

As you refine an idea, you’re pushing in the direction of less
qualification. But you can rarely get it down to zero. Sometimes
you don’t even want to, if it’s a side point and a fully refined
version would be too long.

Some say that qualifications weaken writing. For example, that you
should never begin a sentence in an essay with “I think,” because
if you’re saying it, then of course you think it. And it’s true
that “I think x” is a weaker statement than simply “x.” Which is
exactly why you need “I think.” You need it to express your degree
of certainty.

But qualifications are not scalars. They’re not just experimental
error. There must be 50 things they can express: how broadly something
applies, how you know it, how happy you are it’s so, even how it
could be falsified. I’m not going to try to explore the structure
of qualification here. It’s probably more complex than the whole
topic of writing usefully. Instead I’ll just give you a practical
tip: Don’t underestimate qualification. It’s an important skill in
its own right, not just a sort of tax you have to pay in order to
avoid saying things that are false. So learn and use its full range.
It may not be fully half of having good ideas, but it’s part of
having them.

There’s one other quality I aim for in essays: to say things as
simply as possible. But I don’t think this is a component of
usefulness. It’s more a matter of consideration for the reader. And
it’s a practical aid in getting things right; a mistake is more
obvious when expressed in simple language. But I’ll admit that the
main reason I write simply is not for the reader’s sake or because
it helps get things right, but because it bothers me to use more
or fancier words than I need to. It seems inelegant, like a program
that’s too long.

I realize florid writing works for some people. But unless you’re
sure you’re one of them, the best advice is to write as simply as
you can.

_____

I believe the formula I’ve given you, importance + novelty +
correctness + strength, is the recipe for a good essay. But I should
warn you that it’s also a recipe for making people mad.

The root of the problem is novelty. When you tell people something
they didn’t know, they don’t always thank you for it. Sometimes the
reason people don’t know something is because they don’t want to
know it. Usually because it contradicts some cherished belief. And
indeed, if you’re looking for novel ideas, popular but mistaken
beliefs are a good place to find them. Every popular mistaken belief
creates a dead zone of ideas around
it that are relatively unexplored because they contradict it.

The strength component just makes things worse. If there’s anything
that annoys people more than having their cherished assumptions
contradicted, it’s having them flatly contradicted.

Plus if you’ve used the Morris technique, your writing will seem
quite confident. Perhaps offensively confident, to people who
disagree with you. The reason you’ll seem confident is that you are
confident: you’ve cheated, by only publishing the things you’re
sure of. It will seem to people who try to disagree with you that
you never admit you’re wrong. In fact you constantly admit you’re
wrong. You just do it before publishing instead of after.

And if your writing is as simple as possible, that just makes things
worse. Brevity is the diction of command. If you watch someone
delivering unwelcome news from a position of inferiority, you’ll
notice they tend to use lots of words, to soften the blow. Whereas
to be short with someone is more or less to be rude to them.

It can sometimes work to deliberately phrase statements more weakly
than you mean. To put “perhaps” in front of something you’re actually
quite sure of. But you’ll notice that when writers do this, they
usually do it with a wink.

I don’t like to do this too much. It’s cheesy to adopt an ironic
tone for a whole essay. I think we just have to face the fact that
elegance and curtness are two names for the same thing.

You might think that if you work sufficiently hard to ensure that
an essay is correct, it will be invulnerable to attack. That’s sort
of true. It will be invulnerable to valid attacks. But in practice
that’s little consolation.

In fact, the strength component of useful writing will make you
particularly vulnerable to misrepresentation. If you’ve stated an
idea as strongly as you could without making it false, all anyone
has to do is to exaggerate slightly what you said, and now it is
false.

Much of the time they’re not even doing it deliberately. One of the
most surprising things you’ll discover, if you start writing essays,
is that people who disagree with you rarely disagree with what
you’ve actually written. Instead they make up something you said
and disagree with that.

For what it’s worth, the countermove is to ask someone who does
this to quote a specific sentence or passage you wrote that they
believe is false, and explain why. I say “for what it’s worth”
because they never do. So although it might seem that this could
get a broken discussion back on track, the truth is that it was
never on track in the first place.

Should you explicitly forestall likely misinterpretations? Yes, if
they’re misinterpretations a reasonably smart and well-intentioned
person might make. In fact it’s sometimes better to say something
slightly misleading and then add the correction than to try to get
an idea right in one shot. That can be more efficient, and can also
model the way such an idea would be discovered.

But I don’t think you should explicitly forestall intentional
misinterpretations in the body of an essay. An essay is a place to
meet honest readers. You don’t want to spoil your house by putting
bars on the windows to protect against dishonest ones. The place
to protect against intentional misinterpretations is in end-notes.
But don’t think you can predict them all. People are as ingenious
at misrepresenting you when you say something they don’t want to
hear as they are at coming up with rationalizations for things they
want to do but know they shouldn’t. I suspect it’s the same skill.

_____

As with most other things, the way to get better at writing essays
is to practice. But how do you start? Now that we’ve examined the
structure of useful writing, we can rephrase that question more
precisely. Which constraint do you relax initially? The answer is,
the first component of importance: the number of people who care
about what you write.

If you narrow the topic sufficiently, you can probably find something
you’re an expert on. Write about that to start with. If you only
have ten readers who care, that’s fine. You’re helping them, and
you’re writing. Later you can expand the breadth of topics you write
about.

The other constraint you can relax is a little surprising: publication.
Writing essays doesn’t have to mean publishing them. That may seem
strange now that the trend is to publish every random thought, but
it worked for me. I wrote what amounted to essays in notebooks for
about 15 years. I never published any of them and never expected
to. I wrote them as a way of figuring things out. But when the web
came along I’d had a lot of practice.

Incidentally,
Steve
Wozniak did the same thing. In high school he
designed computers on paper for fun. He couldn’t build them because
he couldn’t afford the components. But when Intel launched 4K DRAMs
in 1975, he was ready.

_____

How many essays are there left to write though? The answer to that
question is probably the most exciting thing I’ve learned about
essay writing. Nearly all of them are left to write.

Although the essay
is an old form, it hasn’t been assiduously
cultivated. In the print era, publication was expensive, and there
wasn’t enough demand for essays to publish that many. You could
publish essays if you were already well known for writing something
else, like novels. Or you could write book reviews that you took
over to express your own ideas. But there was not really a direct
path to becoming an essayist. Which meant few essays got written,
and those that did tended to be about a narrow range of subjects.

Now, thanks to the internet, there’s a path. Anyone can publish
essays online. You start in obscurity, perhaps, but at least you
can start. You don’t need anyone’s permission.

It sometimes happens that an area of knowledge sits quietly for
years, till some change makes it explode. Cryptography did this to
number theory. The internet is doing it to the essay.

The exciting thing is not that there’s a lot left to write, but
that there’s a lot left to discover. There’s a certain kind of idea
that’s best discovered by writing essays. If most essays are still
unwritten, most such ideas are still undiscovered.

Notes

[1] Put railings on the balconies, but don’t put bars on the windows.

[2] Even now I sometimes write essays that are not meant for
publication. I wrote several to figure out what Y Combinator should
do, and they were really helpful.

Thanks to Trevor Blackwell, Daniel Gackle, Jessica Livingston, and
Robert Morris for reading drafts of this.