Humans are born communicators. Just think about how much you’ve communicated with each other this week. You walk up to someone and you just know what to say. So why do we have difficulty writing? And what can we do about it?

My theory is that the challenge with technical writing is not with communication itself, but rather the constraints we impose on ourselves. We are suffocating the writer inside us, and as a result, our writing.

Like programmers, let’s hack our way out of this mess with a few tricks that get our fingers and brain working together to write fluently.

Write in plain text

Free your mind by writing in the closest format to thought, plain text. If you’re writing in AsciiDoc, you’re already employing the primary brain hack I use to write fluently. Way to go! If not, your journey with AsciiDoc starts now. All the hacks that follow become possible once you start writing in AsciiDoc.

Using a plain text format like AsciiDoc, you efficiently encode information, transcribing it into its purest form. And there’s little to no ceremony to get going. More important, it offers a clean separation of content and presentation. You can focus on content and get a beautiful result. We like to say with AsciiDoc, you write once and you can publish everywhere.

When we moved from paper and pencil to the computer to write, we gained a lot of things, but we also lost some. One of the things we lost was the ability to just whip out a sheet of paper and start scribbling on it. Or at least, this capability was lost for a few decades.

All of a sudden you needed to think about a file name and where that file lived on the system. You needed to worry about losing your work because you didn’t save (and saving forced you to deal with the file name and location issue). You had an interface that forced you to think about structure and formatting of your document, and features like auto-correct to prod you to fix irrelevant issues. In effect, you had to make the tool happy in order to write comfortably.

Some then tried to write inside angled brackets like HTML or DocBook. We put so much damn clutter between you and your content that your words get lost.

AsciiDoc, on the other hand, is very approachable. It just makes sense to writers and for writers. Plain text is easy to pass around and share. Since it works just like other source code, you can use the same tools and workflows. No formal publishing workflow is needed (or you already have one with git).

Writing fluently is channeling your thoughts through your fingers and onto the screen. You want to have as little distraction—​as little friction—​in that channel as possible. That’s why I love plain text. It gets me back to feeling like I’m writing on paper, but with all the benefits that computers bring. I can just plow away the distractions. I can revise. I can automate. Above all, I’m writing!

Answer a question

Most of us are OK with writing e-mails. We don’t consider this writing. Someone asks you a question, you hit reply and type away.

The same thing is true for Twitter (and other social networks). Think about how easy it is to tweet. The Twitter bird asks “What’s happening?”, you just fill in the blank. You’re a communication machine!

Notice these forms of communication are responses to questions.

When it comes to documentation and other long-form writing, such as writing a README or tutorial, we clam up. All of a sudden we have to think about structure. What’s the beginning, middle and end? The prerequisites? The audience? It’s no longer just question and response. So why not make it more that way?

Write like you are answering a question. Start with an outline of questions, answer those questions, then go back and change those questions to statements in the final version. Make it more like writing an e-mail response. Fill in the answer.

In fact, start writing documentation directly in your e-mail if you have to to get yourself writing. With a question just sitting out there, you’ll be compelled to answer it. Gradually shape that content into a README, tutorial or some other form of documentation.

The key is to get the information out of your head and onto the page. In doing so, you’ve unloaded all that information from your brain and now it has free cycles to organize, shape and rewrite it.


We tend to write by cramming sentences together on one long line. Worse is if you use arbitrary wrapping. This leads to reflows. You need to scissor sentences to move them around.

Think about how you write code. You put each statement on its own line. Anders Nawroth of Neo4j introduced me to the power of writing using the sentence-per-line technique which follows the same style. This technique transformed my writing process.

In sentence per line, you write a paragraph like you would a bulleted list, except you waive the bullets. Like HTML, endlines in paragraph content are insignificant in AsciiDoc, so this mode of writing is supported by default.

  • feels natural (matches how we write code)

  • keeps changes localized (because it does not cause reflow)

  • easier to diff

  • can easily rearrange sentences or disable sentences

  • can add commentary at the sentence level (more on this in a minute)

  • encourages shorter sentences; edit with a knife!

  • warms up your writing

  • helps you think about what you’re writing

Highly recommended. It also makes comments more effective.

Write in comments

Just like code, AsciiDoc supports line and block-level comments. This allows you to take content out of the flow either temporarily or permanently.

There’s no way I can write anymore without comments. My document has as many comments as it has (visible) content.

Comments give you some place to put ideas, notes, reminders and drafts directly adjacent to the source. They work really well when combined with sentence-per-line. Once you write using sentence per line, you can use line or block comments quite effectively to try out content, swapping it in and out of place. This let’s you soft delete content, making revision less scary.

Comments also let you talk back and forth to each other in a document. It’s a lightweight revision mechanism and notation system. Use //INITIALS: to leave a comment. Use //! to indicate you are rewriting a line.

Power thesaurus

Ever since grade school, I’ve sat with a thesaurus at my side when writing. Nowadays, I use an online tool, specifically This is the biggest secret to what makes my writing intriguing.

I want to start by defending the thesaurus. When I first starting using it, people would tell me, “using a thesaurus will cause you to use big words you don’t know and what you write will sound unnatural and lack your own voice.” First of all, this is bullshit. Don’t listen to these people. I didn’t, and it paid off for me.

A thesaurus is not at all about trying to find big words that you don’t know. Sure, you are going to learn words as a side-effect of them being in proximity to the words you are looking for. This is a good thing. But that doesn’t mean you’ll pick them, at least not until you become comfortable with them. A thesaurus is like a treasure map for the words in your mind.

When you write, you are transcribing your thoughts into the written word. In other words, you are listening to yourself think and writing down what you hear. Sometimes, you hear the words clearly. Sometimes, you don’t. You might get the sense of the meaning you want, but your brain isn’t matching that meaning to the word. But you’d know the word if you saw it. Enter the thesaurus.

When this happens, just type %%%% in your document and finish the sentence or thought. Then, open up and start shopping. Dig through the closet of your mind to find the word that has that meaning. What you’re doing is getting your brain to recognize the word it wants. This is partly conscious and partly unconscious. Keep saying the sentence in your head and see if the next word in the thesaurus feels right. Is it something you might say? Make sure you hear it in your own voice.

I even browse the thesaurus to get ideas about what to write, to provide a spark to get started. What’s best is a very broad thesaurus that provides a wide net of ideas.

The thesaurus is a mediator between your unconscious and conscious. Your unconscious knows what it wants, but your conscious isn’t getting this information. The thesaurus is the secret to getting that information across the divide and onto the page. You aren’t going to select words that aren’t your own, but you will select better words that you would have without it. I use it all the time.

If your brain still isn’t making the connection with the help of the thesaurus, get up and take a walk, a shower or just doing something else for a few minutes. While away from the screen and the pose of writing, your brain will start working on the idea in a background thread. This usually helps unlock the thought or memory you need to continue writing. Perhaps it’s your brains way of rewarding you for the break :)

Visualize progress

The hardest part about writing is getting started. The preview can be very motivating tool to help you get your feet wet, as well as help you keep the big picture throughout the writing process. I constantly keep the preview open and toggle from my editor to the preview as I write.

There are lots of ways to get a preview. My personal favorite are the browser extensions, in particular the Chrome extension. I can visit any local or remote AsciiDoc document and view the rendered HTML instead of the source. It even updates automatically (aka Live Reload) when the underlying source document changes. A truly amazing tool.

And all along the way, I see the document in a semi-published state, so it motivates me to keep going.

You don’t know how valuable it is to see what changed until you have it, then take it away. Imagine for a second that you are working on a development team and someone changes a bunch of code, the code isn’t in source control and there’s no other copy. I’m sure you’re feeling a little bit of panic right now. That’s how we often write, only worse because we have multiple copies of the same document in binary format that we can’t diff.

Source control and diffs are just as important for writing as for code. In fact, in a lot of ways, writing is coding, except the language is a human language instead of a computer language.

Source control and diffs give you all the same confidence for writing as it does for code. You commit the first version, then you can change the content to your heart’s content and know that you can always go back to the first version. Commit to make a new checkpoint and continue. It lets you edit with confidence and without fear. You can venture further away from the wall and try stuff because you can always revert back or compare it to where you started.

While revision control is usefully locally, it’s even more powerful for teams. You’ll find yourself reviewing docs changes just like you do code changes. And it’s absolutely essential for writing where there are little to no guards against an incorrect change (with code, we at least have tests to validate the change).

GitHub, in particular, makes "code review" for docs very effective. Package up your change as a pull request. From there, it offers the typical source diff. This allows you to see the lines, and the characters within those lines, that changed. If you use sentence-per-line, this drastically improves the effectiveness of this view because you don’t get noise caused by reflows.

But the truly powerful feature is the rich diff. In this view, you see the differences in the rendered out. Both the old and new version are rendered and you get a diff of the rendered output. It also folds parts of the document that haven’t changed so you can really focus from the reader’s perspective on the change that was made.

With these two views, you will never again experience that panic when different people start editing a document (or at least a lot less and you’ll have a way to manage or revert the changes).

Couch read

The best way I’ve found to get a big picture view and also catch all the little errors while editing is to do what I call a couch read.

When you do a couch read, find a comfortable couch to stretch out on, bring up the document on your phone or other portable device and start reading through it from the top. No typo is too small to escape a couch read. This works because it shifts your locus of attention to reading (and only reading).

Humans only have one locus of attention. Every desktop application and web page wants this locus of attention. When you are at your desktop, your attention is constantly being tugged on. Even when you are looking directly at the document, there’s still a very good chance something will pop up to distract you. And your brain knows this. So it sucks at focusing on the details in the document. On top of all that, the font is too small (the font is always too small).

When you’re horizontal on the couch, you are relaxed and you are hyper focused (at least, that’s my experience). Now I can really dig into the text and think about what is being said. I’m also focusing on one paragraph at a time. This gets me totally in the moment, in the words.

You’ve also hacked your brain to be in the readers shoes, making a clear switch from producing to consuming. Because you are far away from the keyboard and the temptation to switch over to your editor and wordsmith, you are forced to read the words that are there. This makes you painfully aware of what you wrote and whether it flows.

I strongly encourage you to “couch read” all your documents.


If you use the techniques I presented to you today, and combine them with your own brain hacks, you’ll find that writing does not have to be difficult. And it can be very satisfying. Write with pleasure. Thank you.