Almost 25 years ago, I wrote a blog post with the title ‘jumping ship slowly’ about leaving Windows (XP was awful, it was mind boggling to me that Vista managed to make people nostalgic for XP). My advice remains the same:

Don’t try switching OS first. The OS is the most easily replaceable bit in the stack. Switch applications first. Most ‘Linux’ apps are cross platform. They’ll run on Windows, and the few that don’t will run in WSL2. You can switch out apps one at a time, and take the time to get comfortable with the alternatives.

Once you’re comfortable not using any Windows-only apps, changing the OS but using all of the same applications is very easy to do. Changing OS and application stack at the same time is an enormous obstacle.

I believe this is also why a lot of corporate and government Linux migrations fail: they try to change everything at the same time and that’s too steep a learning curve.

@david_chisnall
After 2k Pro, XP was not a fond experience for me.

I multibooted OS/2 and Linux until I got early access to test Vista, and it was a revelation (once NVIDIA straightened up their drivers for the new WDDM).

I slowly adopted open data formats, then programs, then finally switched to Alpine Linux for myself and my family.

A long road, but as you noted, it need not be terribly difficult (in many cases).

@Brett_E_Carlock Got any advice or resources you particularly like for Alpine? I'm starting to play with it to replace several things, and I feel like I'm having to relearn a lot of fundamental stuff.
@noodle
For me, it was _very_ unlike the Debian-deriveds I used, so same lack of familiarity, but I found the cognitive load of using it much lower once I got over that unfamiliarity.