How to Write Something Compelling

Dear Everybody,

The most compelling writers express the biggest ideas in the fewest words, and they make ideas simple and universal. Here’s how they do it.

This is a piece of writing (there’s a beginning and an end).

To write something, you have to move from left to right (draft new sentences; create fresh text).

But to write something well, you have to move from right to left (locate your favorite sentences and delete them).

I call this process discovery by deletion. Figuring out what you want to say by deleting what you don’t.

Justin Mikolay @jmikolay

Secretary Mattis and I once worked on a message to all DoD personnel. First draft ~900 words. Second draft ~600 words. Tenth and final draft 172 words. That draft said more than the first. #discoverybydeletion

Let’s take this a step further. When Jack Dorsey founded Twitter, he set an arbitrary character limit.

The limit forced everyone to make choices. It mandated discovery by deletion and in many cases improved writing quality.

ᴅᴀᴠɪᴅ ᴘᴇʀᴇʟʟ ✌ @david_perell

Twitter makes you a much better writer at the level of words and sentences. But if you want to master paragraphs and overall structure, you need to write essays.

But deleting — moving from right to left — isn’t enough.

If you want to write something compelling, you have to add an axis to your creative process. You have to make the ideas bigger and the word count smaller at the same time.

For five years I was a speechwriter for U.S. government officials (David Petraeus, Jim Mattis, and Leon Panetta). My job wasn’t to write for them, it was to help them write. We exchanged hundreds of written products and every time they edited, they moved up and to the left: at the same time they were making the draft shorter, they were making the ideas bigger.

In every creative process, there's a moment when you have to grab the subject by the scruff of the neck and lift it up, like an animal carrying its young.

Ever wonder why Naval Ravikant never seems to bump up against the character limit? It’s because for him the character limit is irrelevant. His self-appointed task is to write as many characters as necessary, and none more.

The essence of editing is to revisit original ideas … to expand them when necessary … and to ask yourself if you can put them any shorter. Masterful communicators make the creative process a vector, not a scalar.

The opposite is how Lincoln described a fellow lawyer:

He can compress the most words into the smallest ideas of any man I ever met.

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Once the writing is “light” enough (few words, big ideas … like a helium balloon), there’s one more thing to consider.

To write something simple, you have to move from right to left:

But simple isn’t enough. People appreciate Apple products because they’re simple. Simple is great. But the most under-appreciated thing about Apple products is that they’re also universal. Two-year-olds around the world can use an iPad.

If you want to design something attractive, you have to add an axis to your creative process. You have to make the ideas simple and universal at the same time.

Here’s how Andrew Fleming West, the first Dean of the Graduate School at Princeton, described people who don’t put things in universal terms:

They have an intensive knowl­edge of one thing, which is very well indeed, with extensive ignorance of most other things, which is not well at all. Their narrow intensity of vision along some little lane of knowledge seems to blind them to all the scenery outside. They are thus isolated from the general world of knowledge, and often from their fellows in the same department. … Such isolation cuts men off from a community of sympathy.

From this evil flows another, namely, the loss of simplicity and universality in the scholar's powers of expression.

The writer is caged and mastered by his restricted theme. His language, or rather his dialect, becomes technical, arid and lifeless. This makes it hard to maintain a reciprocal reading interest.

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Helping others write this way taught me how to help myself write. The challenge is to inhabit my own brain and channel myself, to look at the ceiling and ask, “What am I trying to say?”

I remind myself that reading, thinking, and writing aren’t separate acts. They’re three parts of one act (the act of creation) and three processes within a larger creative process:

• Reading is filling myself with ideas. It’s a process of “knowing again” what someone else has already learned and passed along.

• Thinking is clarifying and ordering ideas. It’s a process of expressing ideas in deliberate sequence.

• Writing is reflecting ideas back to myself in written form. It’s a process of knowing … so others may know again (including my future self!).

Let any one of these processes be in haste and it will stifle the others. Keep each in rhythm and they’ll fuel each other. One idea will collide with the next. The ship will sail under its own power.

As Woodrow Wilson put it in the context of political progress, creative progress:

Draws its springs gently out of the old fountains of strength, builds upon old tissue, covets the old airs that have blown upon it time of mind in the past.

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Sincerely, 

Justin