I got off the Windows treadmill when Windows 95 came out. I was young, but lucky enough to have some education and some contact with clued-up people and I got the whole Emperor's New Clothes thing.
I went straight to Slackware Linux (where I still am) which has been a great education and got me into Solaris, Debian, Red Hat, SuSE, CentOS, Gentoo, Ubuntu and MINT.
I have never needed to run a Windows desktop since. Ever. Period. You can do it, and you can run your DOS and Windows stuff if you really, really need to.
In 99% of cases it's just fear, ignorance and laziness stopping people getting off of Windows.
Even Mrs Turgid has found herself at work booted off of Windows/IE/MS Office onto google's cloud stuff. There was no training provided and none required. IE no longer required either.