I'm not sure it works for platforms but for programming languages, I've found it helpful to think about how I got familiar and comfortable with the ones I'm good at and try to replay those experiences and activities for the what I'm trying to learn.

Perhaps something on those lines?

Generally speaking though, my interest and confidence with GNU/Linux has come by it being much more tinkerable (and requiring of tinkering in the early days) than Windows. I needed to mess with a lot of stuff to get things working and that helped me learn a lot of stuff. Things are much better now but all those hours helped.