My introduction to Linux began with Mandrake in early 2000s. I had no idea what to do with the new system on my computer, though. Subconsciously, I did not realize why to swap win with lin. Windows was much comfortable and immediate. At the same time I had fun with Linux installation and OS exploration
A couple of years later I got a job related to Linux and my enthusiasm to this system was revived. My next job was related to windows unfortunately. But I managed to integrate Linux in my network infrastructure. I switched to Linux even on my workstation, because I was fed up with antivirus's CPU and disk i/o consumption
It was 2007 and apparently then I got carried away with this system enough to try different tastes. And even FreeBSD just before Gentoo. Why not FreeBSD? Just in case of hardware issues with the network adapter on my brand new laptop. It was annoying even to perform software update in that case. From 2007 to 2012 linux was the only system on my computers. Gentoo, Ubuntu and Slackware in about equal proportions
Then in case of tasks change for a few years I used MacOS X only. And in 2017 I switched to Mint. I'm not saying finally, though
I believe migration to Linux is not about my (or yours) abilities and 'tries' primarily. It is about tasks and state of technology. That is, I switched to a new system immediately, when my tasks and the level of hardware support began to correspond to it