Leaving Windows and Microsoft 365 After 30 Years

I’ve been a Windows user for over 30 years. With a brief detour to Linux on the desktop in the early 2000s, every machine I owned was running Windows, both private and professional. I always had a soft spot for macOS, but something always got in the way. The price premium, the butterfly keyboard disaster, the missing ports, the Touch Bar, or simply software I relied on that wasn’t available on macOS. So I stayed on Windows.

That changed three weeks ago.

Separating Work and Private Life

After more than 25 years of blending private and professional IT, I decided to draw a clean line. My Lenovo X1 Carbon Gen 10 running Windows 11 stays what it is: a work machine. For everything private, I picked up a MacBook Pro with an M5 Pro, 1 TB of storage and 48 GB of RAM.

Apple Silicon fixed almost every complaint I had about Apple hardware. No more thermal throttling, no more compromised keyboard designs, ports are back and the Touch Bar is gone. The hardware is simply very good, and it was the final push I needed.

Breaking Up with Microsoft

Switching the hardware was only half of the story. I also decided to cut Microsoft out of my private life entirely. No more Microsoft 365 Family, no more OneDrive.

This was easier than expected. I’m already well embedded in the Apple ecosystem with iPhone, iPad, Apple Watch and AirPods, so iCloud covers most of what OneDrive did for me. Beyond a bit of office productivity and a browser, I don’t actually depend on Microsoft software for anything in my private life.

Coming Back to Self-Hosting

I’ve been running my own services on Linux for over 20 years. A few years ago I shut everything down and migrated to managed services, which made sense at the time. But circumstances change, and I had good reasons to spin things back up.

The obvious candidate to replace OneDrive was Nextcloud. I already had the operational experience, the infrastructure and the mindset for it. More on the Nextcloud setup in a follow-up post.

The Keyboard Problem

One thing that drives me absolutely mad is the keyboard layout. I’ve lost count of how many times I accidentally closed an application when all I wanted to do was type an @. Fortunately, I had already fallen into the mechanical keyboard rabbit hole, so I had a Keychron K8 Pro sitting around. I fitted it with the appropriate macOS keycaps and swapped the Brown switches for Epomaker Creamy Jade switches. Problem solved, and it sounds a lot better too.

What Actually Works

Most things just work. Collabora Office does its job well, I was able to reuse my dotfiles without any major changes, and apps like WhatsApp, Signal, Threema, KeePassXC and XCA run without issues. Instead of Thunderbird I’m now using native Apple Mail, which covers everything I need.

At work I’m still fully on Microsoft, and that won’t change anytime soon. But I genuinely enjoy the small challenge of learning a new platform.

In the end it’s a bit like switching between a manual and an automatic gearbox. At first you think you’ll never get used to it again, but a few weeks later you just switch cars as if nothing happened.

Follow me on this journey. :)