My Writing Workflow

Writers tend to obsess about their writing tools and routines. I do, at least. I probably spend way too much time futzing around with pens and pencils and notebooks and text editors and document styles. Although I don’t really have a routine. But I enjoy the tools of writing as much as I love actually putting words on the page. Besides, I need something to do when the words aren’t coming.

Despite my constant tinkering, my writing workflow has been fairly consistent for the last few years. Here are the tools I use and what I do with them.

Capturing Ideas and Organizing Files

Nearly everything I write starts as a simple text file. All of the formatting that rich-text editors like Word and Pages add to documents is distracting and undesirable, so I generally stick to plain text. And while there are some excellent cloud-based editors (like Draft), I prefer to use actual files that I keep on my system and can edit whether or not I am connected to the Internet.

I keep all my files in a Writing folder in my Dropbox account, and I try to keep my folder heirarchy as flat as possible. In that folder are two more folders, _Abandoned Writing and _Writing Archive. (Those underscores are part of the folder label, so they sort to the top of the folder’s contents. I could just name the archive folder _Archive, but I have lots of archive folders on my system, and it is hard to tell them apart in search results if I don’t add a descriptor.)

Whenever I have an idea for something to write about, I create a new text file in my Writing folder. Most of my ideas come when I only have my iPhone, since it is always in my pocket. I usually just start a new file using Byword, but the quickest way is using Drafts (not to be confused with the cloud-based editor, Draft) to capture those ideas because I have an action set up to upload new ideas to my Writing folder as a text file with the first line as the filename. The Drafts workflow is faster and easier, but for some reason I have a hard time making it a habit.

If my idea is going to be a bigger project, like an article that requires research or an eBook I need to write in Word, I will create a folder for it so that I can keep notes, outlines, images, research, and versions all in one place.

Occasionally I sift through my Writing folder and dump the things I’ve given up on into the _Abandoned Writing folder. And sometimes I pull things back out of the _Abandoned Writing folder and write them after all.

When I have finished writing something, I move it to wherever it goes next (a blog, usually) and move the file to the _Writing Archive folder. Every year or so, I move a bunch of the archived files to my long-term archive.

Writing Hardware

I do most of my writing on a 13″ Retina MacBook Pro or a Mac mini connected to a 24″ Dell UltraSharp display. Mostly the laptop, though. I like to get out and write at coffee shops or CoCo Uptown a few times a week. The Mac mini gets more use in the summer, when my basement office is the coolest place in the house. In the winter, that space is uninhabitable.

I have an iPhone and an iPad Mini that I can use to edit my files, but I don’t very often. I used to do most of my writing on my iPad 2 with an Apple Wireless Keyboard, but then I decided a small, thin-and-light laptop with great battery life is a much better writing tool than a tablet. The 11″ MacBook Air may actually be the ideal writer’s laptop, but I like the extra power and gorgeous Retina display that comes with the 13″ Retina MacBook Pro.

Writing Software

I have tried a ton of writing software, and I have pretty much settled on two: Byword and, reluctantly, Microsoft Word.

Byword + Markdown

I do most of my writing in Byword on my Macs, iPad, and iPhone.1 Byword is a clean, simple text editor for writers, and it is my favorite of the many text editors I have tried.

Most of the time I write in full-screen mode, so there is nothing on my screen but my writing. Theoretically, this helps me focus on writing and prevents me from getting distracted by everything else on my computer. I think it works, sometimes.

Writing in text is nice and simple, but I still need to format text and insert links. To keep it simple, I use Markdown syntax instead of trying to write directly in HTML.

Markdown is pretty minimal compared to HTML, but the markup still distracts from your writing. Byword dims the markup elements to make them less distracting, and adds some basic formatting to help you see what you have done. (This is all just in the way Byword displays your files; the actual contents remain unchanged).

When it comes time to transfer your writing from Byword to WordPress, you can just use File > Export > Copy HTML to copy the HTML. Byword will take care of adding HTML tags for headings, italics, boldface, bulleted lists, and so on. Or, if you are using the Jetpack plugin in WordPress, you can just activate the Markdown module and copy and paste your writing as-is.

By default the Byword mobile apps want to use /Apps/Byword as the Dropbox folder to sync. You can change this to /Writing in the settings, though.


I don’t really like writing in Word, but the simple fact is that while Markdown works great for writing that will end up as HTML, it has some flaws when converting to other formats. Currently, as far as I can tell, there is no converter that will preserve heading styles when converting from Markdown to RTF or Word format.2 And you will have to convert if you want to publish an eBook or submit your manuscript to a publisher. If you start in Markdown, you will be doing a lot of tedious reformatting in Word. Starting in Word in the first place save you a lot of time and tediousness.

Word also has a helpful sidebar index that allows you to navigate long documents by using the headings. Just go to View > Sidebar > Document Map Pane to turn this on. The Document Map Pane is essential for navigating any document longer than a few pages.

Of course, there are some serious downsides to writing in Word. For one, it is an incredibly bloated editor for something as simple as an eBook or legal brief. The UI is cluttered and unintuitive. And the Mac version of Word generally kind of sucks.

But when it comes to documents not destined for HTML, Word still gets the job done better than anything else, so that is what I use. (Update 2014-12-28: Google Docs may actually be a bit better than Word for drafting, just because its table of contents includes links to headings by default. That’s convenient for writing, and you’ll need to do that when finalizing your eBook anyway. I haven’t found an easy way to do create a linked table of contents in Word.)


Ultimately, it does not matter what tools you use as long as they help you put words on the page. But if you do enjoy your tools, you might do more with them. In theory.

I do not have the discipline to establish a writing routine like many great writers. Instead, I carry around my writing tools all the time, feel guilty whenever I am not actively writing with them, and write in furious bursts of productivity that last anywhere from a few minutes to a few days.

The rest of the time, I try to do related things like reading the news, researching topics I want to write about, or jotting down ideas. And I spend a lot of time attempting to summon inspiration. To an outside observer ignorant of the delicate nuances of my writing style, this might look suspiciously like I am just sitting on the couch watching a terrible barbarian movie. Or manually eliminating all the extra spaces from Lawyerist’s CSS file. Or browsing Twitter. Or playing video games. Or writing a blog post about writing.

But that is not what I am doing. I am hard at work, and eventually it pays off and I am able to summon inspiration and some focus long enough to sit down at my computer and churn out a few thousand words.

  1. For occasional editing in a browser when I don’t have access to my desktop or laptop, I use Writebox

  2. If I could convert headings properly from text files to Word files, I would probably write longer works in Ulysses

Published by Sam Glover

Sam Glover is a lawyer and the founder and Editor in Chief of He also works with lawyers on motion practice and appeals, and is President of the board of directors of HOME Line, a nonprofit Minnesota tenant advocacy organization.

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    1. You might be right, but even if it does work properly, a command line converter isn’t actually all that useful to me. Maybe there is a way to create a script that you can access from the right-click menu (OS X), but I’m not motivated to figure it out.

      I’d much rather pay for Marked, except that it doesn’t do headings properly either. Brett Terpstra’s comment on my support thread gives me some hope that it will soon, though. When it does, he’ll make at least one sale (me).

    1. I have, but Evernote kind of sucks for writing. It doesn’t support header or blockquote styles in rich text, and it doesn’t support Markdown for plain text. I need one or the other.

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