I had some CAD experience in college, "formally" trained, i.e. I had a class and lab for drafting and Autocad, and have always been fairly mechanically and tech savvy, but had never done anything with CNC until one day, that was my job.
Tight ass (cheap) boss at the time, bought a used one-off early '90s 5'x12' CNC Plasma table with a Hypertherm HD 1070 (I think) and an old Burny controller. The table was the company that made its first and only foray into the world of plasma, they went from making gas torch tables (I assume oxy-accetelyne), made one plasma table, then said forget it, and started making lasers or water jets, I forget now which, not important to the story, just suffice it to say, I had some old ass equipment to work with, and no real technical support.
We started out with BobCad as our CAD software dujour, it was decided before I was hired, and based solely on price and Airgas' "CNC Guy's" recommendation, it may be better now, but you'll never get me to say much nice about them, I imagine if you searched my user name and Bobcad, you'll find related form posts around the web, from about 10 years ago of me ready to drive to Florida and have words with some of their "support," staff. Boss finally saw the light, and we went whole hog with Solidworks. I did way more than just 2D sheet parts, I did all the drafting and plans for everything we made too.
As much as I cussed BobCad, they did make us a "custom" post processor, for our ancient plasma table, that while a little cumbersome, did a half way decent job of nesting parts on a sheet, and once I learned the table, and tweaked my kerfs, lead-ins, lead-outs, etc. I was able to just program entire nested sheets for specific products. I had a binder, with pictures showing what the cut sheet of metal looked like and program number on it. We had an old desktop in the corner running Burny Server in a DOS window 24/7, that the Burny talked to via RS-232. I trained a handful of the weldors how to call up a program and run it, all they had to do was load a sheet of metal, type the program number they wanted from the binder, and hit start.
The actually cutting stuff is the easy part.
It'd be worth while to take a night course, or if there's any free online classes, to get an idea of how to handle the CAD side of things. Most software has tutorials though, so teaching yourself isn't difficult, and there's countless tutorial videos on youtube for most popular software.
I learned by doing on the CAM and CNC side, and while I succeed, I made things a lot harder on myself that need be. I had a big book for our Burny controller, that actually did a decent job of teaching me G codes, with tutorials, and various trial shapes. Once you start getting a hang of the codes, or at least can reference a chart or something, everything is easy X Y coordinates. Really though, as much as software has progressed, I bet actually knowing G code isn't necessary, even when I was doing it for a living, it got to the point that I only used it if something screwed up and I need to trouble shoot.
The real trick in my experience was the post processing CAM, once you have your parts designed, you know how to cut them, then you need to maximize your efficiency and minimize wasted metal.
Regardless, it's not the insurmountable voodoo witch craft that some like to make it out to be. If you can drive a car, you can probably learn to run CNC, some exceptions apply of course.
I kind of wrote a novel, sorry.