Windows (for many years) -> Ubuntu (for a year) -> Arch Linux (for half a year) -> Void Linux (literally 2 days) -> Artix Linux with runit (a month) -> Gentoo Linux (another month) -> Debian (finally, I don't plan on changing it).
Windows 95 -> 98 -> XP -> 7 -> 8 -> OSX -> Arch (1 month) -> Gentoo (1 year) -> VOID (3 years) -> NixOS (4 years) (transitioning to Guix System now)
For reference, this was my editor hopping journey which started during my OSX days since I learned to program during this time:
Sublimetext -> vim -> neovim -> emacs