From Microsoft fanboy to living in Apple's walled garden: What I learned
Photo by Ruthson Zimmerman on Unsplash

From Microsoft fanboy to living in Apple's walled garden: What I learned

I was a Microsoft fanboy for a very long time. From when Windows ruled the world in the 90s through to the late 2010s. But I now live in Apple's walled garden. This is the story of how that happened (for the better, I think) and what I learned in the process.

First, I wasn't a blind Microsoft loyalist. I loved Windows, but I didn't like Windows Mobile despite the cool hardware HTC offered at the time (remember the HTC Diamond?). I never could get my hands on a Zune. I liked Windows Phone's Metro design, but it always fell short on apps at a time when I was mad about installing as many as I could.

LinkedIn app for Windows Phone

So I tinkered with Android phones and custom ROMs. I used an iPod shuffle for a while before I lost it. An iPhone for a little longer—six months or so—before I broke it and moved back to Android. My workstation ran on Windows XP, Vista, then 7, and later 10. Windows was


Sure, I thought Macbooks were cool but I was just too comfortable with Windows 10 for work and browsing. Until my employer asked me to switch to a Mac. I resisted for two years. There was a feeling of brand loyalty (even when I told myself that brand didn't matter as much as the product serving a need) but everyone on the team was on a Mac and, after a point, moving from Windows to Mac was inevitable.

I hated it at first. The weird trackpad gestures for navigation, the dock without a Start button, the menu bar and its confusing tree of functions, the horrible Cmd/Option keys messing up muscle memory for keyboard shortcuts that I'd spent two decades learning... I could go on and on.

Six weeks later, I didn't know why I'd been against using a Mac. It was fun!

The trackpad gestures made me move my hands around a little more often than I was used to, but they soon felt intuitive, kinetic and exciting. The dock was easy enough to work with and the lack of a Start button didn't make a difference at all. Those Cmd/Option keys took getting used to, but I was back to using keyboard shortcuts like a champ again.

On the Mac, everything worked exactly as expected, every single time. No matter what I threw at it, it chugged along like a well-greased engine and elegantly at that. There was the occasional system crash (that guy with too many Chrome tabs and extensions, that's me) but I hardly remember them.

Two years on, I live in Apple's garden.

There's the Macbook Air for work, the iPhone I bought because I wanted a smaller phone and it syncs with the Mac seamlessly, and the iPad Air so I can play with Procreate. My flatmates' workstations, a Mac Mini and an iMac, finish the lineup. I live in Apple's garden—a walled one, for sure—and I'm loving it.

A first look at Windows 11 earlier today prompted this piece, as I started thinking of how my taste in computing devices has changed over the years.

Is it just me or does Windows 11 look a little like the Mac? 

That centered taskbar, search bar, and settings panel at least look like the Mac's dock, spotlight, and settings screens.

No matter, the new Windows looks like it'll be more fun. It makes me want to go and get a laptop with Windows 11 for a test drive. Almost.        

So that's the how, but what I learned from this experience is that most of my resistance to switching from Windows to Mac wasn't out of brand loyalty. It was inertia.

I was too comfortable with 'a way' of doing things and simply didn't want to change. I'm glad I did though. :) Something similar happened with the relatively recent switch from Android to an iPhone, but that's a story for another time.

I still like Windows, but I now like Macs too. I can now work with both when I need to. I know I don't want to change platforms and tools again in the future, but I probably will. There's gonna be a little resistance to change—I'm as lazy as they come—but I now know from lived experience that changing platforms/devices/tools can be good. It can be fun, making life easier. Let's hope that's motivation enough to overcome inertia or sloth.

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