Following My Own Advice: Writing Tools (Premium)

I have used Microsoft Word for decades for all the obvious reasons, but I have also experienced a series of escalating issues that make this app less than ideal. And as I do with all of the other apps and services I rely on, I’ve experimented with using other writing apps many times, and at one point I even took the radical step of replacing Word with the technical Markdown text editor I was using at the time to write my self-published books.

But nothing is perfect: The editor I had been using, MarkdownPad 2, was no longer supported or being updated, and it required me to install an out-of-date version of a third-party developer SDK as well. I dealt with this for a while, the idea being that using a single app for all of my writing, rather than two separate apps, one for the web articles (Word) and one for the books (MarkdownPad 2), made sense. But I eventually just started using Word again for my non-book writing. The path of least resistance.

I have a love-hate relationship with Microsoft Word, and I always have. For so many reasons. So let me just describe a few of them.

Decades ago, I realized that even as a professional writer, I was using only a small percentage of its features. I long hoped that Microsoft would fix this problem by offering a stripped-down UI that would expose only those features I regularly used by default. And there were several pushes in this direction, like the adaptive menus in Office 2000, the ability to hide the Office ribbon that debuted in Office 2007, the simplified ribbon that debuted in 2018 but only came to Word for the web, and then the personalized toolbar that Microsoft quietly added in 2022, supposedly as part of the Office visual refresh, but I think only in the Insider program. Whatever the details of that last, it’s obvious I’m not the only person who has found Word and the rest of Office a bit too complex.

More to the point, none of these UI changes solved my problem: I don’t see that personalized toolbar in Word today, for example, but even when I did, it would only appear after using Word for some unspecified amount of time, and it was never truly personalized anyway. Nor did it sync to my Microsoft account/Microsoft 365 account (which is another issue I’ll get to below), and because I use so many different computers, I am always reconfiguring Word, which means that I wouldn’t have that toolbar until I had used Word on whatever computer for whatever amount of time.

The lack of full and complete settings sync has long bothered me as well because I configure Word very specifically for my needs. Microsoft Office, like Windows, syncs some settings so that when you sign in to the suite and use the apps, some of the customizations I make auto-apply. But Office, like Windows, doesn’t make it clear which settings it syncs, and whatever the percentage it does sync is small. And so I go through a very specific process of customizing Word every single time I set it up on a new PC. Which, as noted, I do all the time. Meaning several times each month.

I don’t want to bore you with my exact configuration, but I could walk through it in my sleep all these years later: I disable the Word start screen, configure AutoFormat As You Type in a specific manner, make several changes so that Word saves documents to the desktop by default, hide Backstage when opening files, and change how pasting from other programs works. These changes are specific, and they are all over the Word Options window in various tabs and sub-groups, and if I miss even one checkbox, things don’t work correctly. It’s a pain in the ass, and if Word would just, I don’t know, sync my f#$king settings, my life would be a lot less stressful.

Another long-time issue I’ve had with Word is that it doesn’t intelligently take the title of a document I’m writing—i.e. the first line of text—and use that as the file name when I type CTRL + S to save it. What I mean by “intelligently” is that it can’t handle special characters like colons or even apostrophes: Instead, it just cuts off the document name at that character. So when I write a headline like Hands-On with the Office Visual Refresh and then type CTRL + S to save it, Word will save that file as Hands. Seriously. To get around this, I have to remember to copy the first line of the document to the Clipboard, type CTRL + S, paste in the real name, and then remember to edit out characters that can’t be used in filenames, like a colon. Other apps do all this automatically, but Word, the world’s premiere word processor, does not. All these years later.

In more recent years, Word (and, I assume, the rest of Office) has adopted the same enshittification techniques that we also see in Windows 11 and OneDrive, leading to daily frustrations. Because I save to the desktop and not to a OneDrive-protected folder, it constantly nags me to save to OneDrive despite the fact that I specifically go through the complex series of configurations I vaguely documented above. That is, Word completely ignores my wishes and annoys me with a stupid inline notification to “backup” the file I’m working on.

This annoyance can’t be turned off: Word annoys me with this every single time I save a new document and there is no option in the app to disable it. I find that offensive and disrespectful given that I pay for Word through Microsoft 365 and that I am smart enough to use this app how I see fit. But look more closely at that message because there are two identical grammar errors in it. You don’t “backup” a document, you back up a document. Backup is not the correct word in that context, and I find it doubly offensive that Word, an app designed specifically so you can create professional documents full of words, displays this mistake to me every single day. In so many ways, it’s the perfect cherry on top of this enshittification sundae.

It’s also related to the final problem with Word that I will document today: Word’s spelling and grammar capabilities have gotten dramatically worse in recent years, and it’s to the point where I literally no longer trust it. This is ironic for a few reasons. Word is, again, the world’s premiere word processor, and it should offer best-in-class spelling and grammar checking. Microsoft is inarguably a leader in AI, and these technologies should make the spelling and grammar checking in Word (and elsewhere) better, not worse. And, get this, Microsoft is so proud of its spelling and grammar checking capabilities that it offers them to customers outside of Office in the form of the Microsoft Editor as a web browser extension. I cannot stress this enough: Do not install or use the Microsoft Editor no matter which browser you use: There are much better spelling and grammar-checking extensions available (more on this below) and there always have been. And I can tell when the authors of Microsoft posts use this terrible product from the mistakes I see in them. The Windows Insider Program posts are particularly bad.

I have been ignoring or working around these issues for years. For spelling and grammar checking specifically, I long ago turned to Grammarly as a second line of defense: I deal with the spelling and grammar checking issues in Word, paste the document I wrote into WordPress in my web browser so that I can publish it to the web, and then use the Grammarly extension to find all the mistakes that Word missed. And there are always several of them. Every single time: That’s how terrible the Microsoft Editor is.

Well, I’ve had enough. Again. And while I’ve worked to eliminate Word and its multiple annoyances from my life in the past with only mixed success, I am going to do what I did with OneDrive when its enshittification finally pushed me over the edge and follow my own advice and use a tool, or a set of tools, that gives me what I’ve always wanted. That is, I’m going to use a simple app for writing that remembers my configuration changes, works everywhere, doesn’t annoy me every single day by pushing its own needs over mine, generates documents that will always be human- and machine-readable, and works seamlessly with the publishing system I use here on Thurrott.com (WordPress).

All of that is important to me, obviously. But that last bit is critical, and a key reason I stuck with Word for so long despite my issues with it. Whatever I write, wherever I write it, it has to spit out clean HTML with no spurious tags into WordPress. Ideally, I copy the article text with whatever formatting to the Clipboard and then paste it into WordPress, and it’s formatted correctly with clean HTML. And that’s what Word does. It’s the one thing that it gets 100 percent right. (Granted, this is probably a function of WordPress, not Word. But it doesn’t matter. It just has to work.)

I alluded to this shift in My Favorite New Apps of 2023 (Premium) when I noted that some of my in-progress experiments were too new to add to the list of changes I made this past year. Among them was a recent experiment using Typora, a Markdown editor for Windows (and Mac and Linux, there’s even a native version for Windows on Arm) that I’ve been using on and off for years. Typora isn’t perfect, but it comes very close to meeting my needs. Very close.

Typora is a simple app, and I love its minimalist and uncluttered user interface, which can be customized with themes and a wide range of options. Including things like auto-save, which Word lacks. (Word only “auto-saves” with OneDrive, not elsewhere in the file system.)

Typora works with the Markdown markup language that I know well from using it to create many books, but the app also uses simple and obvious keyboard shortcuts for formatting and thus works like a simple word processor. I can type CTRL + B to bold text and CTRL + K to add a hyperlink, just like I do in Microsoft Word. But even the shortcuts that are different—CTRL + 1 to apply the Heading 1 style, for example—or obvious and easily learned. From a writing perspective, Typora is not quite as easy as Word, but given my knowledge of Markdown and experience with this app, I have no issues. And because Markdown is plain text, nothing I write will ever be lost.

This isn’t a big deal right now, but because Typora has Mac and Linux versions, I can use it anywhere, including potentially on Chromebooks, where you can optionally enable Linux and install apps. I have not tested that yet, in part because it kind of doesn’t matter: There are plenty of Android- and web-based Markdown editors that will work fine on Chromebooks if it comes to that. But I will.

Getting the text I write in Typora into WordPress was initially problematic because when I copy the article body to the Clipboard (CTRL + C) and then paste that into WordPress (CTRL +V) and examine the underlying HTML code in its so-called “Text” view (the default WYSIWYG mode is called “Visual”), I can see that its a mess: Typora adds all kinds of spurious hard-coded tags in attempting to transform its clean Markdown into HTML. That’s unacceptable: If and when we change the theme we use on Thurrott.com, those articles could be misformatted in horrible ways.

If there was no workaround to this problem, I couldn’t use Typora. It’s that simple. But there is a workaround: Typora supports an alternative to Copy called “Copy without Theme Styling.” And if I use that instead of Copy, the text I paste into WordPress is as clean as can be. It’s just clean, basic HTML that will work correctly all the time, anywhere.

The issue is that “Copy without Theme Styling” is a menu option with no keyboard shortcut, and as a writer, I prefer to keep my hands on the keyboard. Given Typora’s many customization capabilities, I figured there might be a way to add or change a keyboard shortcut in the app, and so I looked around in the app preferences and Googled it. And sure enough, there is a “advanced settings” button that opens a folder in File Explorer that contains two Typora configuration files in JSON format, another standard, plain-text document format that’s easy to read, even for humans. And you can edit these files to make configuration changes that aren’t exposed in the Typora preferences interface. Including keyboard shortcuts (or, as it calls them, keyboard bindings).

Given my needs, I figured the easiest thing to do was to simply remap CTRL + C to “Copy without Theme Styling.” But I couldn’t get that to work, probably because it’s intercepted by the system, so I set out to find a keyboard shortcut that Windows would ignore, one that would be easy to remember. And I settled on CTRL + M because “m” means “Markdown.”

This works flawlessly. But that assumes two things, that I remember to use this non-standard keyboard shortcut and that I can easily replicate this configuration on other PCs. These are both important: I’ve already screwed up and pasted an article normally (with CTRL + C), and it triggered a weird typo in a URL that a reader noted. And as I pointed out above, I used a lot of different PCs: I have to install this app everywhere and with that configuration I customized.

Installing it is easy enough, though I have to keep track of the license key I got when I purchased Typora (it costs $15). But that configuration is tricky because it involves saving a copy of that JSON file and a copy of the downloadable theme I chose for the app, and both need to be copied to the right (hidden) folder on each PC after I’ve installed the app. I can figure that out, obviously: I can write a simple script to copy them from whatever location to the right folder. But it’s not seamless. It’d be nice if I could just sign into my Microsoft or Google account and have those settings synced automatically.

There was one more issue to overcome.

For all of the spelling and grammar checking issues in Microsoft Word, there was one thing I liked about using that app for writing: Because I use Grammarly in my web browser, I was getting two levels of checking, two passes, one in Word and one from Grammarly. This is important to me because I want my finished writing, what you read, to be as error-free as possible. And so I would need to figure out if this system could somehow be replicated with Typora.

As it turns out, Typora does have spelling checking but not grammar checking. Normally, I’d be OK with that typos are the big issue, and I understand good grammar. But the built-in Typora spelling-checking functionality is a bit too basic. And I really do want that two levels of checking. The answer came from an unsuspected place: Unrelated to this, I recently tested a series of Grammarly alternatives and came across a more minimalist service called LanguageTool that also offers a browser extension. And it was good enough that I had recommended it to my wife, who is also a writer and a Grammarly user. (In, she pays for Grammarly Premium.) Perhaps I could use one of these services in Windows, and thus with Typora, and one in my web browser.

I can: Grammarly has a Windows app that integrates with just about any app that uses text, including Typora, and I can use LanguageTool in my web browser. So I get two levels of spelling and grammar checking from different sources. This seems to work well.

And so the question before me was simple. Do the advantages of Typora, which are many, outweigh the disadvantages, which are few and relatively minor? For me, the answer is clearly yes. And having tested this out on several PCs this past month, I feel comfortable in making this change. I am now using Typora to write, not Microsoft Word. And while it’s not a perfect solution, it’s a great solution. One that has reduced my daily stress levels by eliminating yet another source of enshittification from my life.

What I haven’t described here is why I don’t use other tools. That is, I tested all kinds of other apps and services before landing on Typora, many of which are familiar (Google Docs) and some of which are not. I wanted to document that process, but I feel like this has already gotten too long and I don’t want to bore anyone. Long story short, this kind of switch is like any other switch, in that there are always blockers, and if there are enough blockers, you just move on. In each case, there was some blocker that prevented me from continuing.

And in this case, it was almost always the clean paste into WordPress bit, a problem that is exacerbated by our specific WordPress configuration. Google Docs, for example, has long had issues pasting clean text and HTML code into WordPress, though that problem was solved in part by a WordPress editor update that we can’t use. So I experimented with various Google Docs plug-ins and workarounds to see whether I could cleanly paste from that web app into WordPress. And I can. It’s just too many steps, and I write too much, and publish too many articles, to deal with that. So I moved on.

So here am I. And if this success with Typora continues, I’ll have a new favorite app to write about in 2024. I feel pretty good about that, which is why I wrote this post. But I also know that I will switch again if something better comes along. In many ways, that’s the real point: Use the best tool for the job. And while it’s sad to me that that tool is not Word, that’s on Microsoft. I just can’t ignore that enshittification anymore.