Defenestration: The times I left Windows

Thoughts on other operating systems in the age of the $599 MacBook.

I haven’t always used Windows as my main operating system. I’ve spent lots of time with Linux, macOS, and ChromeOS.

I expect I’ll be using non-Windows operating systems more in the future. Apple just announced a $599 MacBook in a world where Windows PCs are getting more expensive. Google is planning on launching an Android-based Aluminium OS, fusing ChromeOS and Android. Valve is pushing its Linux-based SteamOS into the living room, on VR headsets, and behind.

Yes, there are one billion Windows 11 PCs. But also, the enthusiast energy around Windows is not particularly positive. Microsoft has a real perception problem on its hands, and alternatives might start getting more attention.

But PCs have always been more than Windows. For example: Macs are PCs, too. They always have been!

Rather than predicting how the laptop market is about to transform, I want to look back at my own journey. So, this week, I want to share the times I left Windows for Linux, Chrome OS, and Mac OS X — and why I keep coming back. Let’s see what the past tells us about the future.

Windows Me: My Year of the Linux Desktop

Linux was the first operating system that lured me away from Windows. After Windows Me came out, I had an incredibly rough time with it on my PC hardware. In a search for stability — and because I had a geeky friend who was into Linux at the time — I turned to Linux.

I started with Mandrake Linux — I think it was version 9.1 or 9.2. After installing it on my PC, it was stable. While I had some setup challenges (I’m not joking when I said I had to manually assign IRQ values to my sound card on my first Linux PC), I never had the crashes I had on Windows Me. Linux was rock solid.

Linux was exciting, too. It was a whole new world with a different philosophy about open-source, freedom, and community. Rather than a single operating system and one desktop environment, the community offered a gloriously messy ecosystem of different Linux distributions, desktop environments, and other software.

I enjoyed it a lot. I dual-booted Linux and Windows, using Windows for PC gaming and other software that needed Windows, but I stuck with Linux as my main operating system for years. Windows XP was a big improvement over Windows Me, though, and Windows caught up to Linux in a real way. Eventually, I was spending a lot of time with both Linux and Windows XP. I loved them both.

So why did I come back to Windows? Well, honestly: When I started writing online, it was clear there was a bigger audience for Windows than Linux. I spent more and more time with my Windows install, and I gradually did more and more writing about Windows. If you go back and read the writing I was doing 10+ years ago, however, there was a lot more Linux coverage there. If Linux takes off, I’ll be writing a lot more about it, too!

Interlude: The simple fantasy of Chrome OS

When Google launched Chrome OS, I was intrigued. It was cool that Google based it on Linux, but what was really fascinating was the idea that a laptop could be stripped down to be “only” a web browser.

Chrome OS was desktop Linux for the masses, too. The initial version of Chrome OS was basically just a full-screen Chrome browser window running on Gentoo Linux — no taskbar and no multiple floating windows on screen.

I was more intrigued by the idea back then. The simplicity was appealing. I wanted to believe in the simple, web-based future. But I’ll be honest — for anything beyond basic web tasks, Chrome OS wasn’t there. I remember trying to edit images on the original release of Chrome OS — this involved using Adobe Flash or HTML5-based image editors that were extremely clunky compared to real desktop apps.

That image-editing experience was the canary in the coal mine for ChromeOS. The simplicity was skin deep. Trying to do anything mildly advanced turned into a mess because the web-based software ecosystem just wasn’t mature yet.

Why did I shift away from Chromebooks? Honestly, I couldn’t get my writing done on a Chromebook — even if I was writing about Chrome OS. The image editors didn’t work well enough, and file management was obnoxious compared to desktop experiences. Chromebooks felt like tools for consumption and not productivity. I set them down and refocused on “full” desktop experiences like Windows, desktop Linux, and — yes — the Mac.

Windows 8: My flirtation with the Mac

Growing up, I had PCs. I rarely used Macs. There was a computer lab at my high school where I sometimes wrote essays, and they used Macs. I never liked the Macs in the computer lab. They were shiny, but I remember their one-button mice that felt obnoxious to me as a PC user. I just wanted to get my schoolwork done, not learn a whole new way to use a computer!

Many years later, I was writing for How-To Geek (among other publications) when Windows 8 came out. Windows 8 was a shock to my system — it seemed Microsoft was heading in the way of Windows being a closed platform focused primarily on touchscreen apps. I was in mourning and wondering if I was about to leave Windows behind.

Also, beyond Windows 8, I wanted to write about something new — to expand my horizons. I needed a break from explaining things like how to access the Charms bar with your mouse — what a terrible interface that was. How-To Geek needed more Mac OS X coverage, and I needed to better understand Apple’s operating system. So I bought a MacBook Air.

While I never switched completely to the Mac, I did use a MacBook regularly for a few years. Boot Camp existed in those days, and I dual-booted Windows 8 and Mac OS X on the same PC. I thought my MacBook Air was an excellent Windows laptop, actually! I took it on trips and wrote about both Mac OS X and Windows 8 using the same laptop.

Why did I stop using Mac OS X so much? After Microsoft pivoted away from Windows 8 and decided Windows should be an operating system focused on the mouse and keyboard — and an open platform, to boot — I was less interested in Macs. I felt like I could stick with Windows. Plus, I’ll be honest: My history was with Windows. I preferred the feel of the Windows desktop experience to the Mac desktop. And Windows had a bigger audience — I wanted to serve Windows readers better.

So where does that leave me in 2026?

In 2026, I’m writing this on my Surface Laptop running Windows 11 after stepping away from my Windows 11-powered desktop PC. Windows is the operating system I use most.

I have a MacBook running macOS around here, too, and I’ve reviewed Chromebooks for PCWorld. Readers have recommended Linux distributions to me over the past few years, and I’d like to try more of them. I want to stretch my proverbial wings and dive more into non-Windows desktop operating systems — and I plan to do that soon.

Also, I have a Steam Deck — and it’s a great handheld experience. I’m eager to see Valve do more with it! I love that desktop Linux is lurking there right under the Steam experience, too.

Windows is still my preferred operating system, but I plan on spending more time with Macs. I’m eager to get my hands on Google’s Aluminium. I want to put a SteamOS-powered Steam Machine in my living room. And I’d love to test out more Linux distributions.

Windows always seems to lure me back. Let’s see if that keeps happening!

Heads up: No newsletter next week

One quick note — I’ll be taking a vacation next week, so no newsletter next Friday.

Want something to read in the meantime? Jared Newman’s Advisorator and Cord Cutter Weekly are great, as is JR Raphael’s Android Intelligence. I like their newsletters, and I like them both as individuals.

This week at Thurrott.com

As always, I’m proud to partner with Paul Thurrott on this newsletter, and I’m grateful for his endorsement over the past few years.

This week at Thurrott.com, Paul went hands on with the Google Pixel 10a. Chrome is switching to a two-week development schedule, and Bitwarden is getting support for passkeys on Windows 11.

Plus, Paul Thurrott published a chapter from his forthcoming book for Thurrott Premium subscribers. It’s a guide to making Windows 11 more secure. I love smart configuration guides like these.

Spring is near, and new plants are about to sprout

❄️ It’ll be snowing here in the northeast when you get the newsletter. I’ll probably be outside shoveling snow when this arrives in your inbox! But it’s about to warm up, and I’m looking forward to the world unthawing.

☀️ For a break from the snow, here’s a photo I took of a sunrise many years ago — or was it a sunset?

I’ll email you in a few weeks — I hope you have a great start of March.