DOS to Windows to Mac to Linux: the story of half a lifetime in computing platforms

Looking back, I can see a parallel between my computing platform of choice and my awareness of my own privilege as well as the things that are important for me and that I care about.

Let’s start at the beginning with DOS and Windows.

Unchecked privilege in the personal computing era: DOS and Windows in the 80’s

I was gifted my first computer by my dad when I was seven years old. The year was 1983 and the machine was an IBM XT Compatible running DOS. It had 640KB of RAM and a 4-colour CGA screen. It also came with a BASIC manual. That computer and that manual sparked my lifelong fascination with technology.

This was the 80s and I was a cute little straight blonde kid that passed as white, growing up in Malaysia. I was privileged. I was spoiled. I was a brat.

Computers were fascinating devices that gave me immense pleasure. I loved to tinker and explore. I made games for myself. It was purely hedonistic.

I am also rather stubborn.¹ This meant that I spent the next 23 years on Microsoft’s platforms: first DOS, then Windows. I remember thinking how much potential there was in general purpose computing and in the promise of a platform that wasn’t locked in to a single supplier. And yet, of course, regardless of the plethora of hardware manufacturers, the platform was locked into Microsoft. And Microsoft was Microsoft. By 2006, it had been blatantly clear for years that Microsoft had failed to make the transition from the age of features to the age of experiences. Microsoft was only interested in one thing: exploiting its monopoly position to further enrich itself. What it did not do was respect either the effort or the experiences of the people who used its products.

So, after 23 years, I switched to a platform that did.

In August of 2006, I got my first Mac.

Apple: respect for human effort and human experience

It’s no coincidence that my switch to a Mac came about at around the time that I had started becoming aware of the responsibility we had as makers to respect the time, effort, and experiences of the people who use the things we make. It would take more years before I could articulate that with confidence.

It’s also important to note that my switch to a Mac did not involve any sacrifices. It was seamless thanks to Parallels (which let me keep using my existing software while looking for native alternatives), the web and IMAP email, and free and open source cross-platform apps. I cannot underscore the crucial role that these tools played in allowing me to escape the lock-in of Microsoft’s ecosystem. As I wrote back then: “I still can’t believe that I’ve basically switched to a different platform in less than a day. And by switched, I mean that I am up and running and being nearly as productive as I was on my PC.”

In other words, there were convenient bridges for me to walk over; I didn’t have to brave the rough seas to get to the other side.

Switching would have been much harder to do so if I hadn’t already made a conscious decision to wean myself away from Microsoft’s lock-in by moving to free and open and cross-platform tools earlier. Folks working in freedom technology and decentralisation would be remiss to ignore the importance of such bridges. Both the centralised world and the decentralised worlds exist today as separate islands. Bridges are exactly what we need to be building today to get people from the former to the latter.

When it comes to the topic of computer platforms, being stubborn means that I spent way too much in Microsoft’s walled garden and

My adventure in switching my main development machine from a Mac to Linux