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 @david_chisnall I've been giving similar advice. Start by installing Libre Office and learning to use that. Get Firefox or another browser. Many of the major FLOSS programs provide Windows versions. (as you note)

@bluetea @Brett_E_Carlock

I cheated a bit back then by having a second computer (a dual-CPU P3 that I got very cheaply on eBay because the listing advertised a 'duel processor' machine and not many people knew to search for that typo) that ran FreeBSD and using a remote X11 to run the apps that didn't work on Windows. That was back before x86 supported virtualisation (and Windows on Xen was painful), but now it's very easy to boot a VM and run the few things that don't work (or are painful to install, which is more common) on Windows, and WSL2 makes it trivial.

@david_chisnall
WSL2 was my gateway to Alpine, which convinced me to switch off Windows after 20 years of multiboot/VM Linux usage.

@bluetea