In the classic era of word processing, text was born between MS Word and a printer. Today, it is written and edited on multiple devices and apps, then mailed, printed, copied, pasted, annotated, published, RSSed, shared and re-shared, using all kinds of tools and platforms. Stubborn proprietary file formats fail in this frantic new environment. Plain text does better, but lacks Rich Text’s formatting. Markdown could be our golden gun. If only it looked a little shinier!

So what are the strengths and shortcomings of Rich Text, Plain Text and Markdown1 in this diverse writing landscape?

1. Rich Text

Rich text like MS Word or .rtf is famous for its promise of WYSIWYG (What You See Is What You Get). We can use bold, italics, different fonts and formatting, and we see them right there on our screen! When introduced this was a revolution compared to clunky “Reveal codes”-based formatting, or no formatting at all. But there are downsides.


In Plain Text the text is the source. With Rich Text we see a simulation. What we see may please us, but below the surface our word processor secretly builds a more complex text in code. You can see this hidden world by creating a Pages or Word document, typing “Hello World” and saving, then changing the extension to .zip and unzipping the file. Welcome to 1979! 2


If you are courageous enough to look inside the resulting folder, you may start wondering whether you typed “Hello World” or “Hello Hell”:


Custom formats are heavier than plain text formats. The main issue of custom formats is that the relation between the source code and text—between what we see and what we don’t see—is capricious. Here is what you really get when you work with these formats in 2016:

Bugs and UX Trouble

How do you get out of a list or remove indentation? How do you unlink a word? What about getting rid of that bold formatting, line height, or title size? And how the heck do you place two pictures next to each other? Sometimes it’s not even clear if we are dealing with a bug or bad UX.

Copy Pastasciutta

The predominant challenge of custom formats in a multichannel publishing environment is that they break Copy-Paste. We copy a simple paragraph from a PDF, then on pasting it into our email the English text morphs into an Italian spaghetti Western, with lots of dramatic spaces and line breaks. And it’s not just PDF. With formatted text we never know what we’re going to get when we paste.


While .rtf is fairly established and most Word Processors read .docx, different apps interpret these formats differently. You can’t reliably add RTF or Docx text into your CMS. And just forget about going back and forth between a CMS and a Word document.


Exporting may be “just a click”, but forking your text into multiple versions complicates your workflow. Feedback or alternate edits can’t be easily incorporated back into a master file. Managing these versions quickly becomes a nightmare.


Rich Text will not allow you to touch the source of your document. Maybe the text is in a folder that pretends to be a file, or hidden somewhere “safe from the user”, buried deep in nested folders of spaghetti code, or encrypted in the Fort Knox of a secret database.

Of course, as a bizdev person you love the golden manacles of custom formats. As a regular person writing text in 2016, using different apps, devices, platforms and formats, you do not. And who knows how we’ll feel about .docx in 10 years’ time. Or 30.

Although modern word processing programs can do some amazing things—adding charts, tables, and images, applying sophisticated formatting—there’s one thing they can’t do: Guarantee that the words I write today will be readable ten years from now. That’s just one of the reasons I prefer to work in Plain Text: It’s timeless. My grandchildren will be able to read a text file I create today, long after anybody can remember what the heck a .dotx file is. 3

In today’s multichannel text environment a Rich Text file format creates even more barriers than in simpler times. The notion that you need to install a certain version of an app on a certain version of an operating system to open a file sounds like a joke. In order to be shareable between different apps and platforms, the text itself needs to be free of the shackles of app, platform or device.

2. Plain Text

The only file format that works as expected anywhere is no file format, in other words: Plain Text. And it’s all we need to write our first drafts.

Plain Text means words separated by spaces; sentences separated by periods; paragraphs usually separated by single blank lines. If you are in the writing business, even the publishing or screenwriting business, it’s often all you need.4

Plain Text is straight forward. It helps you focus on what you want to say.

Plain Text is free. TextPad, TextEdit, Vim, your cellphone, your uncle’s 1997 AOL mail app… no jacket required.

Plain Text is light.

Plain Text flows like water. But unlike water, it does not quench every thirst. Be it print, a blog post, a PDF, an email, or even a fax, sooner or later that text will have to take on a medium-appropriate shape to be read. As our words take shape inside a medium, they require visual structure. Business materials need headers, footers, and cover pages. Some texts only come to life when illustrated and enriched with pictures, videos or tables. We want links when we write online. We need footnotes in a white paper.

The transition from Plain Text to formatted text has generally been abrupt and irreversible. You write in TextEdit or Notepad, but once you move to RTF, Docx or HTML there is no turning back. However, text naturally wants to slowly transform from just words to formatted prose. This is where Markdown enters the scene.

3. Markdown

Markup languages, like Markdown, MediaWiki or LaTeX, allow you to structure your words without building an invisible Kingdom beneath the plain text. Unfortunately…

3.1 Markdown Sucks!

You might have tried writing Markdown or editing a Wikipedia entry and hated it, because “Why would I want to learn some new ‘syntax’ for formatting text when I have a tool that does it at the push of a button, and shows me exactly what I’ll get?”5 And right you are:

  • Writing in markup may get you around some copy-paste problems, but plain Markdown always looks messy
  • While Markdown is simpler than HTML, you still need to remember the syntax, and looking up how to add a link every time throws you out of the flow
  • Markup, Markdown, MultiWhatever… these formats have their own compatibility problems

Markdown is not the perfect solution for every type of writer, or every form and stage of writing. But if you do everything from note taking to publishing yourself, it is the most efficient solution to date. If you have a publisher that dictates your writing tools, Markdown is less of an option. But then again, the ability to be more easily shareable than traditional file formats may make that collaboration considerably smoother…

3.2 A Plea for Markdown

Aesthetic opinions aside, Markdown is unbeatable if all you do is bold and italics. Typing # or ## or ### for different headers might look clunky. But, once learned, typing hash signs is faster and easier than taking your hands off the keyboard, finding the mouse pointer, selecting some text, clicking on the Headline WYSIWYG pulldown, and choosing the right Headline level. And unlike those grumpy Style Formats, hash signs always behave like they should.

If you know these three things, *, ** and #, you know enough about Markdown to get started. And the better you get at Markdown, the less friction in your overall writing process. Let’s look at some tougher challenges:


Markdown links can completely ruin the look of your text. It is helpful to see the links right there in the text and not have to fiddle with right-clicks and pop-ups, but if you use too many links in the text it is awful. One workaround is using reference-style links. Another would be to collapse links in the editor, but this comes with those Rich Text Downsides.


Having more freedom with pictures in text is cool. If you want a program that deals with laying out pictures well, use InDesign, or do it in your CMS. Don’t go for Word and, hell, don’t expect your Markdown editor to do everything as well as it helps you get words out. Yes, you can use Markdown in Indesign.6


Tables in plain text have a bad rep. If they are complex they look terrible indeed. But for a handful of rows and columns they can work well: Unlike in Word, you see exactly what is going on. (If you do advanced tables, Word is your enemy anyways—use Excel or Numbers.) They are annoying to create, too; but with some magic…


With MultiMarkdown7 (a souped-up version of Markdown) you can automate tables of content, and with metadata variables you can even build correspondence templates. Okay, that sounds hardcore. And it is hardcore. But you should try it. You don’t need to be a ninja rockstar hacker to understand the basics. And once you do understand the basics, it gets easier to generate a Table of Contents in MultiMarkdown than in MS Word.


MultiMarkdown also has footnotes. The syntax is a little obtuse like links, but they’re squirrelly in Rich Text editors as well. But with a Markdown editor that offers preview you can learn the syntax while clicking.

The better you master Markdown, the faster and easier you move between plain and formatted text. That is where Markdown kills: in bridging Plain and Rich Text, it allows you to continuously form text—from the first random note up to multichannel publishing.

Live Rendering

There are ways to improve Markdown rendering, such as folding it, but if you just render Markdown in place, WYSIWYG, you reintroduce all the issues that make Rich Text editors obsolete, plus add a few new ones. If you try to do everything with Markdown that Word does without it, eventually you start building Word on a language that is not built for WYSIWYG. This is why iA Writer doesn’t hide any Markdown characters.

4. A Contemporary Workflow

We may fantasize the different steps in a writing process as being separate phases that can be controlled and put in a chronological order. In reality, we take notes ahead of writing, yet continue to collect material up until publication. Editing starts with the first draft, and—not only in digital media—it goes beyond publication.8

Separating steps in a creative process is necessary, but flexible workflows are not waterfalls: they overlap, interact, cross-influence, and our writing and publishing tools should allow us to go back and forth as we wish.9 Writing is naughty by nature.


Focused writing is not writing with blinders, it means your main attention is directed to one aspect of the whole process. It is even helpful to consciously move back and forth between two neighboring steps. Markdown allows you not to worry about the thresholds.

4.1 Write And Preview

Moving back and forth between steps in a process is necessary and refreshing. If you love to work in a WYSIWYG editor, or print your text from time to time, or regularly preview it on your blog before publishing, you already know: Definite formatting helps us to take the reader’s perspective on the text. Seeing our text printed out changes our perception of it. You get a similar effect when you swipe away from Markdown and look at your rendered text in HTML-preview.


The effect may not be as striking as the jump from screen to print, but it gives a glimpse of the shape of the text to come. With the feeling of how a reader will see your text, you can go back to your text with fresh eyes. This is quicker as it saves the boring, time-consuming exercise of retyping handwritten corrections.

The conscious switch between Plain Text and formatted text will let you imagine how the text reads from outside.

The deliberate switch between Plain Text and formatted text shows you how the text reads from outside.

4.2 Edit and Publish

The same change of perspective happens when you switch between the front-end and back-end view of your text—once you move the content to your CMS.

If you already write your texts in Markdown, make sure your publishing tool allows you to edit the Plain Text without losing all the formatting. You don’t need to go all in with a Markdown file-based CMS. If you use WordPress you can install a Markdown plugin for the editor. It helps if the writing apps you use support posting to different platforms from the get-go. This is why iA Writer allows you to publish directly to WordPress and Medium:

Publishing directly from your writing app is cool. The key though is that you can Copy-Paste your text back and forth without losing work. Copy-Paste is often faster than pushing lots of buttons. Unless you are a workflow genius, you won’t get around adding some final touches in Indesign, WordPress or .Pages. What good is a publishing tool if it doesn’t let you do things a word processor can’t?


We use different devices to take notes, different apps to draft and edit, we send text to other people, and we use different platforms to shape and publish our words. The production process, and the final shape of our text, has become less calculable. We need more than traditional text formats that lock us into a defined format/app/platform/device framework to cope with today’s complex formatting and publishing reality.

Because of its universality and simplicity, Plain Text gets us further than any file format. Yet, Plain Text editors are not made to visually structure text, optimize complex layouts, fiddle with detailed typography, or interlink text bodies. They are great for finding the right words, but fall short the longer the text gets. A contemporary writing process needs to allow us to freely move back and forth between plain words and formatted text, via automated workflows or copy-paste.

So far, light markup languages like Markdown are the only things that allow this. Markdown may look a bit messy and, yes, all sorts of improvements are possible and necessary. In spite of its shortcomings, it solves complex methodical problems where the traditional separation of plain words and formatted text fails. It allows us to use our text and the file it is embedded in everywhere, independent of device, platform or app. The moment where you move between text and style, package and content, body text and layout shouldn’t be a single point of no return, it must be a phase where you can freely move back and forth. Markdown makes this possible.

If you want more complex formatting options like links, pictures, footnotes and a TOC, use the UI or shortcuts. To improve your Markdown skills with more advanced syntax, get help from a text editor that offers live preview. This also gives you a glimpse of how the formatting will appear early on, allowing you to use more complex markup as you can quickly find any mistakes.

Automation between your cloud service, note app, text editor, and publishing environment is cool, but not essential. What is fundamental is the ability to copy-paste your text back and forth without losing formatting or information. Only a plain text format guarantees this. Configure your publishing platforms to interpret Markdown, so you can move freely between Writing, Editing and Publishing. There are many different ways and apps to do this. And that’s precisely the point. Plain text is light and free and should stay that way. Avoid apps that want to put it in shackles.


  1. Pure Plain Text is text in a plain text file format without any markup language. Plain Text comprehends every file format that saves text directly to file (.txt, .md, .markdown, etc). By Rich Text we refer to all text formats that save formatting information in an invisible layer of inaccessible source code (.rtf, .docx, .pages, etc). Rich Text refers to the mere visual appearance of typographically enhanced text—independent of the file format. Markdown is discussed as Markdown in Plain Text format. Combining Markdown with a closed file format is against the whole idea. Markdown creator John Gruber defines Markdown as “a plain text formatting syntax”. However, in practice Markdown could be written in .docx, or packed and rendered through any other file format. This will cause all sorts of issues, but let’s not get ahead of the argument. 
  2. Why 1979? “On November 29, 1979, the term ‘Microsoft’ was first used by Bill Gates” (From Wikipedia, History of Microsoft). It gets better: “this is a clearly spoofed creation date—it should be a surprise to no incident response specialists that miscreants can alter the MAC times of files on the file system after they’ve been created with freely available tools built for this task. The interesting thing here is that this date is 1 day before the oldest date you can do a search on in the Windows search GUI. Try hitting ‘F3′ right now or going to Start–>Search—you can’t specify a date earlier than 1/1/1980 when performing searches… again, you’d have to do your search from a command shell to find files created on this date.” (From Miscreant hiding techniques: Would the real explorer.exe please stand up? And the relevance of 1979 when doing searches…
  3. Why Plain Text is the Best, by David Sparks 
  4. Words, words, words, by Richard Dooling 
  5. Gradually falling in love with Markdown, by Stu Maschwitz 
  6. Here is one of the many: MarkdownID. Crazy people even found a way to work from Word to Indesign. From Word to Markdown to InDesign: Fully automated typesetting 
  7. “MultiMarkdown is a superset of the Markdown syntax, originally created by John Gruber. It adds multiple syntax features (tables, footnotes, and citations, to name a few), in addition to the various output formats listed above (Markdown only creates HTML). Additionally, it builds in ‘smart’ typography for various languages (proper left- and right-sided quotes, for example).” MultiMarkdown by Fletcher Penney
  8. While collecting notes we get flashes of the future headline, before even thinking about what we want to say. We inevitably rethink what we want to say while writing it down. We usually have to do additional research when editing, and sometimes even when laying out our text. The layout can reveal unseen deficiencies in the text. The limitations of the medium will require us to cut, rewrite or add text to fit the form: this has a healthy effect on the writing style, since it forces us to reflect on what we really wanted to say. 
  9. One of the many mistakes we made along the way of building our own Markdown editor was to become smitten with the idea that a writing workflow can or should be separated into distinct steps, and that these steps should be coded into the file extension. The method works for some highly disciplined authors, but the feedback we got on this setup was clear. iA Writer 3 is still compatible with the previous workflow, but we and most of our writers are happy we have moved on.