💻 Switching from macOS to Windows 10

This is a curious tale. Mostly because I started with switching over to an Alienware laptop for Virtual Reality purposes. Unfortunately, the HDD within the Alienware makes it horrendously slow for anything but gaming. 'Luckily', my Macbook Air decided to throw a fit and permanently disabled the Wi-Fi radio, leaving me with a non-portable work laptop. (In case you are wondering: Wi-Fi dongles are pretty much a no-no on any Mac. They simply lack the necessary drivers to make them work as it's normally built in. Nobody creating these dongles gives one iota about keeping them updated for newer versions of macOS.)

So now I'm kind of stuck on a Toshiba Satellite. It's SSD based, which means it's workable (seriously, just skip HDD laptops, they're basically obsolete). Actually, I was rather happy with it. Was. As now its Bluetooth radio gave up the ghost. Luckily, that is easy enough to repair with a random Bluetooth dongle. Still, it was an ominous sign that I'm also back in the Windows mud. It feels weird to be back.

Anyway, on to the main meat of this article. How does one switch from macOS to Windows in terms of productivity? I wish I could say it was easy, but it simply is not as clear cut as you'd want it to be. The main issue is that after iOS and 'apps', macOS became synonymous with 'used by people who pay money for software'. The result is that over the years, proper Windows software applications have all but evaporated. If you do find a paid app, it's usually very old, not updated and you are left in limbo over whether or not Windows 10 decides that it is compatible with it.

While Microsoft kept bumbling by pulling their operating system into the modern era, software development on macOS flourished. Regardless of the Mac App Store, you can get an application for just about anything you can think of on macOS. And while Windows 10 has improved considerably (especially since its Anniversary Update), the feeling is that developers have simply left the operating system for greener pastures at Apple. The result is an application ecosystem that feels very… ehr… Linux-like. There are applications, but the useful ones feel outdated and more often than not they are not applicable to the Windows 10 UI.

It's a reversal of fortunes. I still remember switching to macOS (then still OS X) in 2009 and being very anxious about leaving certain applications behind. Now it's the exact opposite, and it's not because I need to get used to Windows software again; most of it really is just outdated.

Taking that into account, here we go!

Email, Calendar & Contacts

Let's get this one out of the way first as it's still the backbone for many people in their daily routine. Google knows this, so if you're using Gmail, you can simply open a browser and get on with it. If you're looking at multiple email-accounts, things can get tricky though. Especially when you mix in a few none Gmail-accounts.

On macOS, Apple's own Mail application is pretty functional and gets the job done for multiple accounts. However, it's a bit gnarly and can get its knickers in a twist if you want to access your email in anything but a classic folder hierarchy. And while it does allow for signatures, they are limited and juggling multiple identities could be better.

My application of choice on macOS is Airmail. It has a clean interface, unified inbox, respects Gmail labels and manages indentities and signatures incredibly well. OK, it goes a bit overboard in the settings department, but its recent updates have made those a bit more managable.

So what can you get on Windows? First of all, Windows 10 has a built in Mail application as well. It plays nice with Gmail and other mail-accounts but sadly is a bit under-powered on the identity and signature department. One thing I absolutely hate, is that it tries to emulate Outlook and adds cross-application buttons to Windows Calendar and Contacts. It looks like this is one application, but instead these buttons just launch the other applications. It's rather confusing and, worse, Contacts uses a slightly different interface, breaking the illusion completely.

Looking through the email options on Windows I quickly despaired: here it was very obvious time had stood still on Windows. I almost consigned myself to the Elder God that is Outlook, were it not for Mailbird. This application is essentially Airmail for Windows. It has less (functional) customisation options than Airmail, but its core functionality matches that of Airmail very well - including identities and signatures. If you're a Game of Thrones fan, you'll also be happy with their House-themes and it has built-in support for a few web-services, which includes Google Calendar (you still have to switch a la Google, for different accounts though).

Mailbird can be tried for free, but I've gone with the lifetime pro-version. Seriously, it's worth the money for a good modern mail application on Windows 10.

For a Calendar, I'd stick to Windows' built in option, even though it's woefully under-powered. I simply haven't found anything remotely better as a stand-alone application. The Contacts application is actually good, in that it syncs without trouble to existing Contact-accounts you might have at Google or Apple.

Markdown editing

Part of me wants to scream at this point. Of course, with Markdown being a Gruber-thing, support on Windows seems a bit odd. But where macOS facilitated a renaissance of pure text with iA Writer, Ulysses and many, many others, Windows is a barren wasteland.

So yes, I'm very happy with iA Writer on macOS, though I'd advise Ulysses if you also need to store and order a large amount of these Markdown files (in which case Ulysses can easily replace something like Evernote or rather, Simplenote).

On Windows you've got Markdownpad. And it makes me want to weep. Sure, Markdown is something you can use in Notepad or any bog standard text editor. That doesn't mean a Markdown application should look like Notepad. Besides, Notepad was much cleaner than this… thing. The site mentioned a version 2, so at that point I kind of relaxed, only to realise the initial screenshot on the website was version 2. Oh dear. Now sure that could work, but Markdown has become synonymous with distraction free writing to me. Anything with multiple toolbars and the like is only something I need when I'm actually styling documents, not writing them. Also, it has some not-properly-working issues with Windows 10, meaning even after I kind of got over its looks, I was disappointed.

Luckily, I remembered two options that help here: Q10 and (my favourite) WriteMonkey. The former focuses on distraction free writing and not Markdown per se. It's pretty good for that purpose though. WriteMonkey is more somewhere in-between Markdownpad and iA Writer. You can get it to look kind of like iA Writer, but its Markdown support isn't as comprehensive as you'd like. Still, you can edit it to suit your needs. I've actually written this article in WriteMonkey. It's also feels to be in-between macOS and Windows, if that makes sense. Its interface is weirdly approachable, but not. Oddball, but I'll take it.

WriteMonkey is free, but you can donate to it as well for a 'personalised' version.

Photo editing

GIMP. Yes, I know. I've used it for so long that I am beyond hating it. But at the end of the day, it. Still. Is. GIMP. Even after all these years, its unified window mode is still buggy and it's very clear that its aim is to proide Linux users with photo editing software. Not play catch-up with Adobe Photoshop.

On macOS there are two very nice options in this field: Pixelmator and Affinity Photo. On macOS I prefer Pixelmator simply because I've used it ever since it became available. To me it was one of the reasons to stick with Apple: finally a lightweight Photoshop alternative that allowed me to do everything I needed to do.

On Windows though… No Pixelmator. BUT! Affinity have been stellar at actually creating a Windows version of Affinity Photo. As of now it's still in beta, but already it's so much better than GIMP that you'll want to install this immediately. Performance can be spotty, but I guess that's more to do with the fact that they are just starting out on Windows than anything else. Can't wait to see this develop further.

You can sign up for the (free) beta here. After the beta period it'll become a paid application, which will be under 100 euros and probably worth the investment. If you are willing to increase that investment, than by all means, get Adobe Creative Cloud instead. Affinity Photo will help you with the day-to-day stuff though.

Vector editing

This is very similar to the situation with photo editing. Yes, you can get Inkscape. But like how Illustrator is the sibling of Photoshop, so Inkscape is the sibling of GIMP. No thanks. Again, on macOS there are two options here: Sketch (which to be honest is now more geared towards interface development) and Affinity Designer.

So yes, this is basically the same advice all over again. I'm used to Sketch on macOS, but Affinity also ported Designer over to Windows. Actually, it's already finished and out of its beta period. Yup, get it if you need a day-to-day vector editing application, and again, if you've got the money Adobe Creative Cloud is still there.


This one can be solved pretty easily. On MacOS I used Mischief which I can describe as Paper by FiftyThree for desktop. This means Mischief is pretty much useless without a pen tablet, but if you've got one, Mischief is what you want to use as its infinite canvas feature is divine.

On Windows? Good news everyone! On Windows there's Mischief! Yup, same application, same functionality. Just get a pen and get sketching.


Google Chrome. (You weren't seriously thinking of using Edge, right?)

Office suite

I really dislike word processors. It's not the concept of styling text that annoys me, it's the backward process they bring to the table in actually doing it. Word and its ilk are still a pain when considering Markdown editing, though granted the new versions in Office 365 are (like Windows) getting better and better. Apple's iWork (or whatever they call it these days) isn't that much better as it lacks inter-operability, but by Jove, Keynote alone is worth its weight in gold.

Getting that on Windows basically means PowerPoint; that kind of defeats the purpose of finding a Keynote alternative. Still it's your only bet. If you can live without all the fancy-schmancy documents, and just want to occasionally put an image in a header and a page count in a footer, get LibreOffice. The interface will make you claw your own eyes out, but it works, it's free and it has a very nice PDF-export function. If you're locked into Excel. Well, you need Excel. No way around it.

In all seriousness though: get Office 365, especially when considering…

Cloud storage

If you are on iCloud Drive, good news: it works on Windows as well. Don't expect any advanced syncing and sharing options, but if you've got a synced Desktop and Documents folder in your iCloud, you can simply work with it on Windows. It also has an option to download your iCloud photos, but really, you don't really want to. It's a one-way trip mostly and uploading photos requires you to dump it in a folder and hope for the best. It's really clear Apple lacks their Photos app for Windows, meaning photo support is mostly an afterthought.

iCloud Drive allows for a weird, non-elegant bookmark syncing option through a Google Chrome extension, but after wiping ALL MY BOOKMARKS TWICE ON BOTH MY WINDOWS AND APPLE MACHINES, I'd severely advice against using it. If you do feel adventurous be very, very sure to have a backup available.

The best option on Windows is OneDrive. Especially as it comes free with Office 365, meaning that if you need Word, Excel and PowerPoint, this really is a no-brainer. Integration is great (even though it's incredibly pushy about you using it) and its only negative is its positively ancient 32-bit filename length requirement. Why? WHY? I mean, sure I get why, but still, WHY?! If your filenames and paths exceed this limit, you may want to skip to Dropbox instead, but otherwise OneDrive provides unmatched value. (Besides, you really want to keep using Dropbox after all that?)

Did I mention OneDrive comes free with the rest of Office 365?

Password manager

1Password has a great Windows version these days. It's still partially in beta, but the new Chrome extension and the Windows 10 app make it function in the same way as you are used to on macOS.

Syncing your vault can be a bit tricky though if you don't use Dropbox. iCloud Drive doesn't sync the vault that-would-be-in-iCloud Drive to Windows, so your best bet is to use a paid-for 1Password personal sync account. Another option is to just store the vault in OneDrive, which it allows, but becomes an issue on macOS where OneDrive isn't a properly and directly supported option. Sure, you can point it towards the folder but that's it. Throw iOS into the mix and you're stuck to Dropbox or a 1Password account as OneDrive simply is not an option there.

If you are using LastPass, this will not be an issue as it works through sync regardless. Just keep using it.


I'm one of these unicorns that have no problems whatsoever with iTunes. On macOS. On Windows however, it's Satan's spawn. Slow beyond measure, not adhering to normal window rendering and it'll crash when you even look at it.

Unfortunately for my music library, it's mostly linked to iTunes. If you've got a streaming option, just go with that (Spotify actually has a better application on Windows than on macOS).


While the built-in Groove Music application may not be the best music app you can imagine, you can download your iTunes music files and play the library through Groove instead. It's not pretty, but at least it works smoothly and doesn't make you want to smash your screen because iTunes attempted... something. Do take into account that this requires you to keep iTunes installed in case you've got any rights-protected files.

Window management

In case you are wondering if I never Alt-TAB'ed or don't realise the joy that is Windows-TAB, rest assured I know all about those shortcuts (and Windows-CTRL-left/right for good measure). Sadly, I'm quite… specific when it comes to placing windows on my screen.

On macOS there's this tiny app called Moom. It lets you resize and move windows on your screen based on a grid layout. It keeps me sane. Literally. I become incredibly anxious when windows just 'float about'. Now, you may not experience this same kind of anxiousness, but if you do, or simply want a way to order your windows on ehr… Windows, there's Divvy.

Divvy does the same thing as Moom, but requires a shortcut to invoke rather than being attached to the Minimise/Maximise buttons like on macOS. Thank the heavens it exists though. This was of course the first application I bought for Windows 10. However, it does seem a bit old-fashioned and I'm kind of scared development on it has ceased.

Operating system

Yeah, well it's Windows, right? How can you possibly replace macOS with Windows? The good news is that Windows 10 is not Windows Vista. Not by a long shot. Vista was of course responsible for me jumping ship to Apple in the first place. (I mean, an operating system that instantly overheats its host hardware because it's constantly listening to music being played in the background that might, possibly, in some instance, be illegal? Which you can't disable? Bye bye!) And while Windows 8 was an actually courageous attempt to redesign Windows, it was a few steps too far and too early.

Windows 10 didn't start out great though, like Windows 8 it tried to do all these new things, but at the same time was bogged down by its legacy. Ever since the Anniversary Update however, this has changed for the better. The old dialogs and Windows XP-like dialogs and settings boxes have disappeared to the deeper layers of the OS; you'll probably run into them because in such cases you know what you are doing.

Likewise, duplicate settings are gone. This one was a pet peeve of mine. Windows 8 and 10 initially had this bizarre situation in which you had two Settings dialogs. One in 'old' Windows style, the other in 'new' Windows style. Worse, sometimes both styles referred to the exact same option and only one of them would actually respond to changing it. Other options were completely gone in the 'new' style, but were still important enough to actually need them, requiring you to spelunk through Windows nether regions in search of the 'old' settings. I'm incredibly grateful this has now changed for the better. The old vestiges are not removed completely, (why on Earth of all things is the screensaver dialog still the same?) but it has been cleaned up and now works coherently.

If you are thrown back it's because you are invoking it yourself purposefully for some arcane reason, or because whatever hardware or software you are using is simply not primarily meant for Windows 10 to start with. Unless Microsoft decides to simply kill everything pre-Windows 8 in one fell swoop, I'm afraid this classic appendix will remain with us a bit longer.

Actually using the OS itself, is rather fine.

Scary, isn't it? I was actually surprised how much Anniversary Edition just worked. Yes, my Bluetooth died, but that seems to be more hardware related than software. Yes, very occasionally some setting flips and you can start a Google-powered expedition into the heart of darkness, but these are exceptions caused by older software. If you stick to Windows 10 and software meant for it, nothing seems to go wrong. Of course, the collorary here being that the Windows application ecosystem is in a dire state as I explained at the start of this article, which means you are kind of forced to use older software.

This creates somewhat of a vicious cycle. You may want to switch to Windows 10 and in all seriousness it can handle your wishes, but the software you crave might simply not be there or be outdated, providing you once more with those classic Windows issues in all their unseemly glory. Chicken & egg. Catch-22.

Of course, this is all from my personal perspective. If you add games to the equation, there's simply no contest. Windows 10 it is (even though, yes, Windows 10 renders a set of older games inoperable). If you want to dabble into Virtual Reality, macOS is not even a viable alternative. And if you're into iOS or macOS development, well let's pretend nobody even thought of that.

If I needed to wrap it all up in a single conclusion, I'd say Windows 10 is good. Not great, good. It works, it lacks software, but the OS itself is on course for something far greater. I don't feel handicapped on Windows 10 and when returning to macOS I actually miss some tiny tweaks and options (Windows-E, HOW I'VE MISSED YOU).

On a devil's advocate note, I really don't get the massive hate for Windows 10 from both sides of the fence. The Apple side seems 'reasonable' in that it's tradition (which really is the worst reason to stay the course), but for Windows users the meddling with the Start-menu and other mainstays seemed to be like dagger through the heart. Well, it isn't. Windows 10 is not perfect, but damn it: it's a pretty good alternative these days.