Dylan Tweney

How to write - and how to avoid writer's block

5 tips for getting started writing when it’s not easy
Dylan Tweney 6 min read
How to write - and how to avoid writer's block
Set a timer, like this cute Pomodoro, for 25 minutes. Photo credit: David Svensson

If you’ve been following the team-writing process I outlined a couple of weeks ago, you’ll reach a point where you have an assignment brief (however brief it may be) and an outline. Now, you’re ready to write.

In some ways, this part should be the easiest. You’re well-prepared, and you’re not staring down a blank page. Quite the contrary: My team-writing process gives you a roadmap that spells out exactly where the writing needs to go and what needs to happen at each point.

What you need to do now is fairly straightforward:

  • Write through the outline until you have a complete first draft
  • Take a break (get a cup of tea, or let the draft sit overnight)
  • Go through your draft line by line to revise it and clean it up as necessary
  • Share the draft with the rest of your team

No problem, right?

In fact, a lot of the writing advice you’ll find in books and online won’t apply at this point. With a well-structured team-writing process, the challenge at this point isn’t so much about discovering your voice or getting the creative juices flowing: It’s more about filling in the outline and creating the first draft of what the client wants.

In the simplest case, you start at the top of the outline and go through it section by section, writing paragraphs that correspond to each bulleted (or numbered) item. When you reach the end, you’re done with the first rough draft.

If the team has prepared a good outline, you should have everything you need to create this draft right there: Examples, sources, references, links, a writing style guide, and so forth. Ideally, the team has already spelled out the specifications for what you’re creating in the assignment brief, so you know what length you’re aiming for, along with any other essential characteristics, such as style, guidance on headlines and subheads, and so forth.

Still, problems do crop up. So here are some tips for writing through your outline with minimal hassle.

Write the way you speak. Business writing tends to get too stiff and formal, with many complex sentences, dependent clauses, and excessive passive voice. I think this is because people get it into their heads that they need to de-personalize the copy or write in a more “official” style because they're writing for an organization. This never works out well.

Instead, start your writing by putting down on the page, as directly as you can, what you would tell a friend about the topic. If it helps, imagine telling your mother, your significant other, or a curious and intelligent niece or nephew about it. Leave out the casual chitchat phrases you’d put into a normal conversation, but otherwise, put what you’d say straight onto the page.

If it’s too weird to imagine talking to someone or too difficult to translate that into typing, imagine writing an email to a friend or coworker you like and trust.

Some people I know find it helpful to speak aloud as they write — to test sentences out by walking around and saying them out loud. When they sound right, they sit back at the computer and start typing.

Other people (including myself) have found it’s sometimes easier to dictate a section of text. Turn on your computer’s speech-to-text dictation and just start talking to it.

Don’t start at the beginning. The first paragraph is often the hardest. I often find it difficult to write a proper introduction until I know the shape of the entire article. As a result, it can be much easier to write that first paragraph after you’ve written everything else.

If that’s the case for you, start your draft with the outline’s first major section, not the introduction. After you’ve written that first section, move on to the second, the third, and so on until you complete all the major sections of the outline. (Or bounce around: The sequence in which you write these sections is irrelevant.)

After you’ve written through the entire body of the piece, write the introduction. Finally, write the conclusion.

Writing the body of the piece first lets me discover how I want to frame the overall piece. Writing the introduction is a lot easier after that because I can create an introduction that sets up each of the major points I want to hit, using a tone that corresponds to what I already wrote.

I write the conclusion last because I want the final paragraphs of the piece to echo the introduction, restating those main points but in a different way. If I have already written the introduction, the conclusion is easy.

On the other hand, for some assignments, I can’t even start until I know how the first paragraph or two goes, so use what works for you.

Give yourself blocks of focus time. The Pomodoro technique can work extremely well at this stage: Set a timer and focus on nothing but writing out the draft for 25 minutes. Don’t do any supplementary research, don’t tab over to check your email, and don’t answer any Slack messages: Just write until the timer goes off. Then, take a five-minute break: walk around, check your email, or get a cup of tea. Repeat as many times as you need to.

In practice, I find it hard to type continuously for the full 25 minutes. That’s okay. My writing often goes in little bursts: Five minutes of silent thinking followed by two or three minutes of furious, rapid banging on the keyboard. I find that it’s helpful to give myself permission to stare out the window or to stand up and stretch in those gaps.

The trick is not to do anything else with the computer, like checking email or Reddit — and not to get more than a foot away from the keyboard. Mute your notifications so new emails or Slack messages don’t disturb your flow or tempt you away from the writing screen. Definitely don’t check the phone while you’re in focus mode. With my phone, I enabled a setting so that when I flip it face-down, the phone goes into “do not disturb” mode. I use that feature a lot.

In short, find a way to focus, but not with so much rigidity that you feel trapped. Stretching and staring out the window might be part of your process (it is for me). But pay attention: If you spend 25 minutes staring out the window and find that you haven’t typed anything by the time your timer goes off, you might need to give yourself a slightly more restrictive set of rules.

Also, my breaks between each Pomodoro are usually 10 or 15 minutes, not the five prescribed in the “official” method. It seems to work well for me: I wrote about 20,000 words between mid-January and mid-February using this method.

Focus on one section at a time. Whether you’re using Pomodoros or not, try setting goals for each writing session. A good target is to write through one section of your outline—just one. Sit down and write out that one section. Then, take a break and do something else. (Reward yourself with five minutes on Reddit, get a cup of tea, or go for a walk around the block.) Come back and write another section. Repeat as needed.

Give yourself a word count target. If you can easily write 100 or 200 words, set that as a target for your work session. Plant yourself in front of your keyboard, and don’t move until you’ve hit your word count.

Plan your next work burst before the previous one ends. Whether you’re aiming to write for a set number of minutes, to complete one section of the outline, or to hit a target number of words, it’s useful to have some idea of what you’re going to write before you start the session.

So, at the end of each session, spending a minute or two thinking about what you’ll be writing for the next session can be helpful.

Maybe start forming the first sentence you’ll write in your mind. Or plan the arc of the sentences you will be writing. You might even want to write down a few words to get started — but don’t try to write a full sentence. Just note down a partial phrase — something deliberately incomplete. Then get up and take a break. When you return, that idea (or those words) will await you. You will have primed the pump and be ready to go.

The collaborative writing series

This post is part of a 12-part series. Click here to see the rest: A short course on collaborative writing


It’s official: It’s okay to end a sentence with a preposition. In fact, it’s always been okay to do this, as NYT columnist John McWhorter wrote last week. The rule against it (along with the rule against splitting infinitives) originates in the 17th century, when aristocrats with expensive classical educations decided to make “proper” English sound more like Latin by adding rules that English never observed in the first place. McWhorter writes that these grammatical injunctions were part of an effort to make English more elegant, formal, and befitting the language of empire. I’ll add: These rules are also classist, serving to further distinguish the aristocracy from the common folk by the way they talk and write. Such bogus grammatical laws are best dispensed with. Good riddance!

A photo illustration of a round token with “English” written on it failing to fit in a square space with “Latin” written on it.

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