Looking back across 25 years, the operating systems I have lived on tell a story in three acts: a first five years anchored in Windows, a full decade on macOS and only macOS, and then a return to Windows that is still going strong. Each transition taught me something, and each one was less about chasing the newest release and more about picking the tool that got out of my way.

The First Five Years: Windows 98, 2000, and XP

My first operating system was Windows 98, and not because it was the current release. It was simply the easiest one to get so I could load it onto old computers. That was the appeal: I could take a machine apart, put it back together, reset it to Windows 98, and everything was good again. It was a forgiving starting point for someone learning the hardware alongside the software.

Windows ME came next, but it was not stable. At the same time Windows 2000 was becoming available, targeted mostly at businesses and schools because it was built on a different kernel (the Windows NT line rather than the consumer DOS-based line). I remember explicitly that many of my friends skipped ME with me and went directly to Windows 2000. My last Windows release of this era was Windows XP, which was a great operating system. Around that time I switched fully to a Mac, so I am glad to say I never had to use Windows Vista. I skipped every version until Windows 10, jumping straight from XP to 10 when I came back to Windows for work.

A Decade of macOS and Only macOS

I used a Mac professionally for about ten years, and so far it has been one of the most stable operating systems I have used for that length of time. Most of my time was on Intel Macs, since that transition happened during this period, but as I moved onto different projects I also dealt with PowerPC machines running Mac OS. Honestly there was not a lot of difference. Certain apps did not work on PowerPC, but the transition was mostly flawless.

Most of that decade I used a Mac for video editing (I was a video editor for about ten years). At the time we used Final Cut, also made by Apple, and yes there were other tools in the mix (Adobe products, and at some point a transition to Avid Media Composer). For the most part macOS was solid. I had it as a laptop, as a desktop for work, and as a personal computer, and it ran great across all of them. Even my server at the time was macOS based: an Xserve that held all the RAID storage. For a decade the Mac was simply everything.

The Server Evolution: From a Room Full of Machines to the Cloud

My first real introduction to servers was at work, when the company started hosting a room full of them. I never had a server of my own back then, but that was the first time I understood the idea of a machine that did things for me, running in a work setting rather than under my desk. Around the same time, cloud platforms like AWS and Azure were becoming relevant, and suddenly you could run your code on someone else's infrastructure. I also started deploying websites on hosts like GoDaddy using PHP and WordPress. Almost all of it was Linux-based technology, similar to what Facebook was built on.

The shift really happened as the web exploded with mobile users. The back end became more and more important, and it became something users could deploy themselves. That is around the time I moved into becoming a developer, and it lines up with my video-editing years in an interesting way. Back then there was no way to stream that footage across the wire. We had to be in the same room as the servers holding the data, especially once we moved into HD video and the files got even bigger. You could not edit remotely the way you can now. Writing and deploying code, on the other hand, was a natural fit for remote work (you deploy your website remotely, from anywhere), which made it a perfect time for AWS and Azure to take off. Both of those were mostly Linux-centric, even though Windows Azure did support Windows.

By contrast, I never deployed into a macOS server world in the same way. When we did have the option of macOS servers, it was mainly to serve files over the wire with something like Final Cut Server. The internet also was not as fast as it is today. Now I can connect remotely to a machine that sits next to the data and get 1080p at a high frame rate on my screen, so I could technically edit video remotely, which was simply not feasible back then. The tooling and the server technology grew up together. These days, even when I connect to a server I do not necessarily need a graphical interface. A command line is enough to change the settings, and dashboards are helpful for visibility into the full system, but they are really just another management entry point. I know Windows servers exist, but I never used Windows that way. I was never a Windows NT admin.

Coming Back to Windows

When I switched to Windows 10, I was pleasantly surprised by how stable it was compared to Windows XP (which was itself a stable release). I got that same Mac feeling from Windows 10 and Windows 11, where there is no abrupt change from version to version. Most versions are largely compatible with each other, so I honestly do not have a lot of complaints.

By now I have been back on Windows for about a decade. Even while using Windows development machines, most of my target machines have always been Linux: develop on Windows, deploy on Linux. WSL has made it much easier to stay inside the Windows environment while still working against Linux, which has kept that split comfortable.

What the Next Decade Might Look Like

I doubt I would move 100% to something like Linux for development, but I have noticed lately that my usage has become mostly terminal based, driven by agents. Sure, I have a couple of chat applications, email, and a few things that are inherently Windows. But I do not do development in those, so there is a strong case that I could start using a full Linux development environment where I edit the code and deploy in the same place. I wonder about an environment where I run my agents entirely inside Linux. I am not sure that is where things land, but the pull is real.

Twenty-five years, three acts: the first five years on Windows 98, 2000, and XP; a decade of macOS and only macOS; and a return to Windows that is still going well. I am not sure what the next decade looks like, but there is a strong case for a fully Linux development environment, or at the very least a remote one. Whichever way it goes, it fits the same pattern I traced in my history of mobile computing: the device and the operating system matter less over time than the work and the services they connect me to.