I grew up all-GUI windows kid. I actually had a revulsion to the shell, mostly because it seemed unfriendly and scary. In my early 20s I tried to run Plex on a Windows 7 box and it was miserable. I forced myself to lean by switching to a headless arch linux box.
Giving up the idea that CLI = pain (i.e figuring out how to to navigate a file system, ssh keys, etc) for sure was a learning curve, but now I can't imagine using computers without it.