Writing is its own reward. – Henry Miller

The Writing Habit

Writing forces you to think. It’s nature’s way of telling you how sloppy your thinking is.

The ultimate test of how well you understand something is how clearly you can explain it in writing — clear writers are clear thinkers. As a wise man once said: “Everything is vague to a degree you do not realize until you have tried to make it precise.”

When you sit down to write, your mind will rebel. Expect this to happen. That way, it won’t bother you when it does. Keep going. Fight through the resistance. Once you get in the groove, don’t try to sound smart or impressive. Pursue truth and let that speak for itself.

Aim to produce a deliverable or finish once you’ve hit a definite milestone. If you stop at a logical stopping point, you’ll have something to think about between work sessions. Other people can give you feedback while you’re not working since it’s easier to edit a draft or a paragraph than a jumbled work-in-progress.

Focus on the process, not the outcome. It’s impossible to play the long game when you’re checking the score every five minutes. If you want to sustain your writing practice over a long time, don’t write for more than three hours per day. It’s best to stop when you still have some juice and know what you’re going to write next. That way, you’ll be excited to write again the next day.

Make writing a daily habit. A day where you don’t write anything is the enemy of productivity. Days when you don’t write anything are the enemy of productivity. The most important thing: write something every day — no matter what.

Why Write?

Never underestimate the power of words.

Writing regularly will change you. When you become a regular writer, you change how you live. Writing forces you to pay attention. More of the world will pop alive. It motivates you to become more curious about the world. It takes you to a higher level of perception and a deeper level of analysis.

Writing has infinite leverage. It creates luck and serendipity, which makes it the most efficient way to network. Conferences and networking events are good for the short term, but writing is the best long-term strategy. Write at a regular cadence and don’t give up. When you have free time, have a bias towards writing.

For knowledge to become wisdom, it must be carefully, tenderly analyzed from many angles, through many means. Many people don’t write because they’d rather consume more information. Consumption is fun, but it can get out of hand.

The problem with consumption is that it feels so good. It gives you a thin, superficial perspective on the world. Even if you get an accurate picture, it’ll only be two-dimensions. But if you don’t write about an idea, you’ll never have a three-dimensional perspective on it. This is why you should expect 80% of the ideas in the essay to happen after you start writing it and 50% of the ideas you start with to be wrong.

If you’re not careful, consuming all day can become another form of procrastination. This is a dangerous trap. When you consume all the time without producing anything, it’s easy to fool yourself into thinking you’re more productive than you really are.

Growth is maximized when production and consumption are well balanced. Summarize what you’ve learned and use that knowledge to solidify your own ideas.

The Most Important Thing: Nobody Wants to Read Your Shit

Streamline your message. Focus it. Pare is down to its simplest, clearest, and easiest-to-understand form. Make it fun.

Make it so compelling that a person would have to be crazy not to read it.

The 10-Step Writing Process:

  • Step 1: Create a Mega Outline
  • Step 2: Build an Archipelago of Ideas
  • Step 3: Outline
  • Step 4: Write a 2nd Rough Draft
  • Step 5: Re-Write Every Sentence
  • Step 6: 10–15 Sentence Article Summary
  • Step 7: Send to Friends and Ask for Feedback
  • Step 8: Write a 3rd Rough Draft
  • Step 9: Turn outline into a full post
  • Step 10: Publish

The Writing Process: Explained

Mega-Brainstorm

Before you begin, piece together ideas, facts, and stories into a single document. Don’t bother organizing it. Put information in there whenever you read, hear, or experience something that’s relevant to the general idea of the essay. Doing this is trivial because your smartphone is always with you.

Keep adding ideas to your mega-brainstorm until it becomes painful not to write the essay. Goodbye writer’s block!

Archipelago of Ideas

Organize ideas from the mega-brainstorm and build the archipelago of ideas. Think of the ideas in the mega-brainstorm as islands in the ocean. The archipelago of ideas is about building bridges between all the ideas. These bridges give the piece unity and cohesion.

Here’s the template I use.

Outline

Make the outline as simple as possible. That way, you can focus more on ideas and less on the structure. The outline is the most challenging part of writing an essay, and it’s not optional. The first draft is always terrible, but good writing has to start somewhere.

The outline of an essay is like the skeleton of a body. It provides its fundamental form and structure. If it helps, write a stock intro and a stock conclusion to stay focused.

Stock Intro: what is the purpose of this essay? How is it going to proceed?
Stock Conclusion: How did this essay proceed? What was its purpose?

Keep the post in outline form for as long as possible. Outlines force simplicity. They make it easier to see the ideas and move them around. The vast majority of people should write with shorter sentences; outlines trivialize this pursuit.

The outline should be longer than the final version. Organize your outline with subdivisions, sections, and paragraphs. Each paragraph is a stepping stone to your final destination and every one should focus on a single idea. Write ten to fifteen sentences per outline heading to complete your paragraphs.

While creating the outline, keep moving, keep writing, and don’t get bogged down by the details.

The mega-brainstorm, archipelago of ideas, and the outline are elements of production. The purpose of production is to produce. The editing phase comes later. The function of editing is to reduce and rearrange. Produce, then edit. Don’t combine them. Never let production and editing interfere with each other.

Editing

Great writers are great editors. Most great writing starts out as bad writing. Rewriting is the only kind of writing that counts.

The secret to editing your work is simple: you need to become its reader instead of its writer. If you’re struggling to do this, step away from the piece for a few days. Edit as if you have no sunk costs. Reject bad ideas, so good ones are all you have left. Delete the parts that readers will skip. Eliminate the extra detail, and concentrate on communicating what’s important.

Poor communicators ramble. Good communicators leave out unnecessary details. Great communicators treat words as the scarcest commodity.¹

Aim to pass the “Thanksgiving Test.” Ask yourself: Could you talk about this at the Thanksgiving table and your family would get what you’re talking about? Keep in mind that you want to write in the same voice you’d use if you and I were in a bar having a chat.

Rewriting Sentences and Organizing Paragraphs

If you aren’t rewriting, you aren’t developing as a writer. The most important part of learning and remembering is the re-creation of what you have written in your own words.

Read each sentence aloud, and listen to how it sounds. Put brackets around unnecessary words. Read the sentence without the bracketed material and see if it works. Write another version of each sentence, under the previous sentence. Each sentence should flow logically from the one before it and refer to the topic sentence of the paragraph.

Here’s an example:

Original Sentence: Liberal and conservative thinkers stress efficiency of production, as well as quality, and consider profit the motive for efficiency.

Edited Sentence: Liberal and conservative thinkers alike stress the importance of quality and efficiency, and see them as properly rewarded by profit.

Try not to use transitions. If you do, don’t use the same transition too many times.

Seek flow and precision. Shorter is better. Don’t try to impress people with vocabulary; it will backfire. Eliminate words that aren’t used in normal conversation.

Once you’ve rewritten the sentences, re-order the paragraphs so they are ordered appropriately.

Create a New Outline

Re-read the essay out loud. This works because the cadence of breathing and speaking tends to mimic the frequency of the brain’s ability to process words and sentences.

Put brackets around unnecessary words. Read the sentence without the bracketed material and see if it works.

Write a new, 10–15 sentence outline. Don’t look back at your essay while you are doing this. The works because you’ll force yourself to reconstruct your argument from memory. This will distill the piece to its essence. By doing so, you will likely improve it. Most of the time, when you summarize something, you end up simplifying it, while retaining most of what is important. By summarizing your ideas, your memory becomes a filter. It helps you remove what is useless and preserve what is vital.

Once the new outline is complete, cut and paste material from the previous essay. Many things from the first draft won’t be necessary. Keep only what is necessary. Delete everything else.

Repeat this last step as necessary.

Note: An essay is not finished until you cannot edit so that your essay improves. You can tell if this has happened when you try to rewrite a sentence (or a paragraph) and you are not sure that the new version is an improvement over the original. Delete banned words and phrases whenever possible.

To take an essay to the next level, repeat the process of sentence re-writing and re-ordering, as well as paragraph re-ordering and re-outlining. Wait a few days to do this so you can look at the piece with fresh eyes. That way, you can see what you have written, instead of seeing what you think you wrote.

Style and Substance

Effort isn’t something readers want. Substance is. The shorter the article, the less bullsh*t.

Treat every word like it costs you something. Good communication is the ability to say the most stuff in the fewest words. The ability to simplify means to eliminate the unnecessary so that the necessary may speak.

Create People and Avatars, not Descriptions

Humans love characters. It’s why we love cartoons, novels, and movies. Humans have an incredible ability to empathize with characters and put themselves in their shoes.

Invent characters that are fun to follow and easy to remember. Characters are more memorable than abstract generalizations about a demographic.

Use Short Paragraphs

Most people read on their smartphones. They’re busy and on-the-go. Don’t write 8–10 sentence paragraphs unless you’re making an important point.

Long paragraphs should be the exception, not the norm. Keep your paragraphs to five sentences, or less. Short paragraphs will make your article less intimidating and easier to read. Now, when you write a long paragraph, it’ll stand out and be seen as more important. Use long paragraphs sparingly. Save the length for when you need it.

Style

Aim to produce something of worth, beauty, and elegance. Steal stylistically from other writers, as all great readers do.

Write as smooth and naturally as you can and use the same voice you’d use if you and I were in a bar having a chat. Write for a reader who won’t read the essay as carefully as you do. If it helps, lead with something counterintuitive or provocative. Use footnotes to contain digressions. Vary sentence length.² Occasionally, the reader needs a breather.

A pause.

Note: The paragraphs (Rules and Writing Hacks) below are courtesy of Nat Eliason.

Rules

Avoid Adverbs: This one is simple: delete your adverbs. If you’re not sure what an adverb is, the easiest way to identify them is that they frequently end in “-ly.” This is, again, more about pruning than outright abstinence: you can still use adverbs, but save them for when they mean something.

Avoid Repetition: If you use a less common word too often, your writing starts to sound odd. When writing, and especially when editing, make sure you aren’t using the same word too frequently. Don’t repeat an uncommon word in the same sentence, ideally not in the same paragraph, and possibly not for the rest of the section.

Vary Sentence Length: Most of us speak in longer or shorter sentences, and that will tend to come through in our writing. But if you monitor the length of your sentences, and force yourself to make some of them shorter or longer (depending on which you default to), you’ll make your writing sound more interesting. I like long sentences. But a short one every now and then helps make my paragraphs more readable.

Writing Hacks

Use TK: As you’re writing, put “TK” anywhere you aren’t sure of a detail, or where you need to add more context later. One of the main reasons I stop writing or fall out of flow is getting stuck on some detail giving me trouble, and by dropping in a TK to come back to it later, I can maintain the flow. Why TK? Think of it as “To Come.” That letter combination doesn’t appear in any English word, so when you CMD+F for it after you’re done writing, you’ll only find the instances where you used it as a place marker.

When in Doubt, Delete It: The easiest way to deal with almost anything giving you trouble is to delete it. If a sentence is bugging you, delete it. Awkward paragraph, delete it. Confusing section, delete it. You’ll find you never needed it in the first place.

Context Switch: If you can, try editing in a few different contexts, the more varied, the better. Do one round of edits standing at the desk you work from, then do another at a bar after a glass of wine or two. Looking at a piece in different places in different mental states will help you see it differently and develop a more varied voice throughout the piece. You may find, too, that when you look at it in a different context, you think of other material to include you hadn’t thought of before.

A Fresh Perspective

Writing is a fruitful habit. Expressing ideas will help you form new ones and by sharing them with others, your thinking will gain precision.

Make this process your own and improve it whenever possible.

Read to inspire you to write more, and write to inspire you to read more. Through this delicate balance of production and consumption, I encourage you to cultivate your own writing habit.

Read more about David Perell and his work at perell.com.


¹ A Morgan Housel quote

² Inspired by Eugene Wei


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