My Early History with Linux

20 May, 2025

Linux has an undeserved reputation for being difficult to use. Especially for the average computer user. It’s a reputation that I believe is undeserved. That might have once been the case, but it hasn’t been true for the past 15 years or so.

I like to think I’m a good example of that. Why? I’m an arts graduate — specifically, someone with a degree in journalism. Despite working in the software sector for most of my professional life, my technical skills range from rudimentary to non existent. Yet I use Linux extensively in my daily life.

But how did I start using Linux, and free/open source software in general? Join me for a little trip down memory lane.

Starting with Windows

In the early 1990s, I bought my second ever computer1: a 486 running Windows 3.1. While it was nice to have a graphical user interface, there were things I just didn’t like about Windows. And, at that time, Microsoft’s well-documented predatory and monopolistic behaviour was starting to become widely known outside of technology circles.

I didn’t feel comfortable or happy supporting a company like that, but there weren’t many alternatives. The Amiga and the Atari ST were in their waning days. Macs, which I’d used a bit in university, were way out of my price range2. But in or around 1994, a techie friend told me in breathless terms about something called Linux.

I was intrigued. And after doing a bit of investigation, I was even more intrigued. At that time Linux wasn’t exactly easy to install and set up. There was more than a little fiddling and editing of configuration files required, and some compiling needed to be done — fiddling which I wasn’t (and am still not) up to tackling. On top of that, there were very few graphical applications for the Linux desktop in those early days.

Over the next few years, I regularly checked up on how Linux was moving forward, with the vague thought that maybe one day it would be in a state in which I could use it.

That one day came in 1999.

Making the Switch

In 1999, my Day JobTM was technical writer at a medium-sized software company. Off the clock, I was writing for various small publications and doing a bit of other freelance writing. All of that I did on a desktop computer running Windows 98.

One evening, while finishing up a document for a client, Windows 98 crashed. Hard. Taking a good chunk of the document that I’d sweated over with it. I was, as you can guess, less than happy. Luckily, I had good notes and remembered the thrust of most of what I’d written. Still, it took several hours to recover what had been lost.

A week and a half later, still chafing from that incident, I found myself whiling away some time at a Business Depot location in downtown Toronto. There, in a bin by the software section, I found a box containing a CD for Caldera OpenLinux. The price tag on the box was marked down to $20. Not a huge amount, so I decided to take a chance. That was one of the best $20 I’ve ever spent.

A few days later, I popped the CD into a Pentium 300 PC that my wife handed down to me after she bought a newer, faster computer. I followed the installation instructions and was surprised at how smoothly and quickly (at least, for the time) the process went. Within 40 minutes I had a brand new operating system on which I could work and with which I could learn.

Using Linux, The Early Days

I can’t say that I immediately felt at home on the Linux desktop, but then again I wasn’t lost or flailing. The desktop environment in Caldera OpenLinux wasn’t so different from Windows that I couldn’t gradually adapt to it. Sure, there were a few quirks here and there but nothing too challenging to overcome. It just took a little time and a bit of patience.

My initial worries about crashes and blue screens quickly faded, and I got more and more productive with Linux to the point where I was doing all of my freelance and consulting work using it. Admittedly, at the time I was using a mix of proprietary software (like Corel WordPerfect) and free software (like OpenOffice), though I eventually moved to an all FOSS setup. I got work done just as quickly and efficiently as I did on Windows. Maybe ever faster and more efficiently.

My first Linux system also enabled me to grow professionally. At the time, I’d started working the first of a few jobs at which my employers used UNIX or UNIX-like systems. Learning the basics of the command line and its tools gave me a skill which, among others I might have had, those employers found useful.

As a freelance writer, I started penning paid articles and (later) posts on my personal blog about Linux, its software, and my experiences with all of that. Writing those articles and posts was a good way to learn and to share what I’d learned. It also earned me a few bucks. But, of course, that work drew more than a bit of ire and criticism from certain corners of the online world. Mainly from nitpicking, pedantic, and seemingly thin-skinned individuals who took offense at a non techie invading their secret digital garden. Whatever …

That computer sat on my desktop for about three years, after which I switched to a series of laptops. The first of those, with Linux preinstalled (a novelty at the time!), I bought from a now gone and forgotten Canadian vendor called Sub 500 Computers3. When an acquaintance gave me a CD with Ubuntu 5.10 on it a year or two later, my Linux world changed for the better. Ubuntu made Linux easier and more enjoyable to use, and I’ve used with (with a detour or two) since them.

Aside from a couple of dalliances with chromeOS over the years, I haven’t run a proprietary operating system on my own computers since the turn of the century. Happily and productively, in case you’re wondering.

No Regrets

After adopting Linux, my computing world changed for the better. While I still had to use one of those other operating systems, and the proprietary software that went with them, at many a Day JobTM I at least had Linux to fall back on for doing what mattered most.

As I told a friend, I’m actually more comfortable using Linux than using Windows or macOS. People argue that the latter are better because of … whatever reasons. But I always feel less productive, less comfortable, and just diminished as someone who works with technology when I have to work on those platforms. I don’t feel that I’m missing out on anything with my embrace of Linux and free/open source software.

For years, people have talked about each year being the year of Linux on the desktop. The year of Linux on my desktop was 1999. Linux has stayed on my various desktops over the last 26 years. And it’s only gotten better and easier to use as the decades have passed.


  1. My first computer was a Commodore 64.↩︎

  2. Towards the end of the 90s I did flirt, for a time, with using a graphical desktop environment called GEOS in the form of New Deal Office (NDO) that ran on top of DOS. NDO was fun to use but had too many limitations to be my daily driver.↩︎

  3. Fun fact: the main location of Sub 500 Computers in Toronto was housed in a previously-unused office in a car wash in central/west part of the city!↩︎

Scott Nesbitt