I was a Windows user for several years when I decided to switch to Linux, late 2005 or early 2006, I can't recall exactly. I remember that on Windows I was always looking for freeware alternatives to all the paid applications. At the time, I was not aware of the terms 'open-source' or 'free software', and I definitely had no idea about the concepts behind them. On Windows I considered myself a 'power user', I knew my way around and could complete almost any task in Windows XP easily. I kept searching until I bumped into Linux and decided to give it a try.
First it was Red Hat 9 for a couple of days, but I had problems with it at network recognition, and so I discovered Ubuntu. After about one month of dual booting with Windows XP I finally made up my mind and wiped it out, leaving the entire hard disk for a freshly, brand new Ubuntu 5.10. Breezy was practically my first Linux distribution.
I knew when I started that the transition will be tough for me; things are done differently on Linux compared to the way they are done in Windows. And it's pretty hard to get unused with a way of doing things which I used for over six years. But what made me stick to Linux and never return, what kept me getting used to all the new stuff and a new, different way of doing things, was the pure fact that I knew Linux will be different and I must put effort into learning it. I understood that I'll have to learn most of the things again and I was prepared to do it. From the beginning, Linux offered me flexibility and free choice, with no fear of using the software or sharing it using BitTorrent or Direct Connect, for example. And the result is now awesome: I'm a happily and passionate Linux user for three years now, and I'd never go back. I can't imagine going back and leave all this behind.
I think one of the main reasons most of the people try Linux and go back to Windows is that they aren't determined to make the switch, and they can't conceive that there are other ways of doing things than the Windows methods. If something is done differently on Linux, they quickly jump to a conclusion that goes like 'This is not right, on Windows it's done the other way around. Then it's no good.' Or the eternal and already 'legendary' syntax, which Linux users are tired and bored of hearing, 'On Windows everything is easier.' Well, I usually smile now whenever I hear it or read it. Once a person gets used to something, it's harder to do it the other way around afterwards, especially if he is not truly determined to do it or at least give it a good try. Unfortunately a big percentage of Windows users who try Linux reach the conclusion that 'it doesn't work', so they go back.
The 'easier' concept is so relative, and why do I think that? Well, to give a simple example: I got used to rip FLAC files using the flac and oggenc command line tools and I also have several small Bash scripts to ease my work. For me, this method is the easiest and fastest, although there are plenty graphical applications out there for doing this task. Or any other.
I agree, when I first started there were many things which I didn't understand and which I felt that were not right. Believe it or not, it didn't seem logical to me that Linux allows two files with the names, for example, Music and music in the same directory. Was that because it really wasn't logical? Or because I was used from Windows with not having two files with the same name, where the names actually aren't case-sensitive? So no, it was because I was used that way from Windows. Or, to give another example: the lack of Apply buttons in GNOME applications. I just felt like the options were not applied if I didn't have that Apply button there. But I knew it's different, and I embraced it. I kept reading forums and articles, and many tutorials; I started to love what I was learning, the whole development method and the community.
Most Windows users expect the change to be fast and smooth: they expect to find in Linux a similar OS with Windows in every aspect; it's a well-known issue. When they find out it's not like that, all is over.
Windows and mainly closed-source applications drive to a strange mentality. I remember a thread on the Battle for Wesnoth forums, a TBS game for Linux, Windows and Mac, licensed under the GPL, about some guy selling the game on CDs on eBay. Believe it or not, the guy was highly criticised by several users posting in that thread, saying that he should ask for permission or that it's illegal. But still, the game is under the GPL, which means he was allowed to sell it without any legal issues.
I remember I had this friend, pretty techy guy, who decided to switch to Linux. He was pretty determined, so I installed Kubuntu for him and tried to help him and explain the best way I could how to solve his problems on Linux. He was open-minded - I remember he tried to make Alpha Centauri work a whole night, with no intention on giving up. Whenever I could, I tried to help him; and he took my advices and sticked to Linux for a while. Well, eventually, he gave up in the end. Maybe I didn't try enough, or maybe he depended too much on Windows, I'm not sure. The thing is, if I would have tried harder, he would have probably ended up using Linux today.
As a conclusion, I think there's no big chance for a person to switch, unless he truly wants it. Windows users need either good determination for switching, or eventually help from someone who has already been there and knows how to make a convert for the wonderful world of Linux.
Note: This is a later, revised version of the article which I originally posted here.
Updated: Sep 15, 2008