Yo, Brad - welcome. Basically, we take a computer and throw imagination at it until a map appears. Or a piece of paper.
Rummage through the tutorial section til you see a style you like (and a graphics app you have or can afford) and try it out. You may be amazed at what a judicious application of borrowed experience and your own native ideas can do to a blank screen. Again - or piece of paper.
In either case, if you'll be so bold as to do some of your experimentation in public, in a work-in-progress thread, we'll offer tips & advice. That'll be an accelerator for the learning that you simply cannot escape, when using Cartographers' Guild Tutorials, the best thing since the Mercator Projection. Oh... Ahem. Sorry - got carried away there. But really - the tuts do help. What graphics software (or type of pencil) do you have access to or preexisting experience with? And what kind of map do you and this friend want?