My partner finally landed their first real job as a lathe operator and they’ve been going to trade school/working internships in shops for the past three years.
That’s not to discourage you from trying or moving into this as a field you might be interested in studying. I’m fairly ignorant on the subject, but operating a CNC lathe is a heck of a lot more complicated than hitting “print” on a CAD file.
There’s a program (Mastercam) I can run the cad through and it translates it to something the lathe can work with. I wouldn’t be running personally as students aren’t allowed to run it themselves. There’s a guy who does the actual programming and such.
That’s called CAM (computer assisted manufacturing) which helps generate the code. BUT, it’s still not automatic. The programmer has to design a machining process (which tools, in which order). In order to do this, you have to have mastered manual machining because CNC machining is still machining. The machines are “dumb” - they just do what you tell them to do.
Tbf you have Shawn who’s beyond excellent at it so you don’t really need to learn 
New thread title: “Choosing a Shawn to machine a yoyo”
That is true. Shawn is amazing.