Comment by jbstack

You can also mitigate a lot of the "familiarity penalties" by planning ahead. For example, by the time I made the decision to switch from Windows around 15 years ago, I'd already been preferring multi-platform FOSS software for many years because I had in mind that I might switch one day. This meant that when it came time to switch, I was able to go through the list of all the software I was using and find that almost all of it was already available in Linux, leaving just a small handful of cases that I was able to easily find replacements for.

The result was that from day 1 of using Linux I never looked back.