One thing I do is draw test maps. I have a concept in my head of how I want a particular area or region to connect and lay out, and I'll draw test maps until I can get how I want them. Usually those are doodles with circles and triangles, even more basic than the 15-minute from a few posts ago, but in this case I didn't think the details that I wanted to emphasize would show well in that style. I also wanted to test different ways of representing mountain ranges and forests; I haven't done most of this in years, so I'm a bit rusty.
The first image is the raw scan.
The second image is after a few passes through Picasa to take the yellow out and tone down the grid.
If I were I "really" working on a map, I would've scanned this several times by now. Somewhere in here I'd scan it, tweak it, and print it onto vellum for coloring. Someday I'll learn photoshop coloring, but it's fast and easy to do it by hand.
This one isn't quite where I want it to be. The placement of almost everything is good, but I'm not sure about the mountain technique. I like the connected ridgeline, but I'm not sure it's quite conveying what I want. Time to browse the cartographers guild. :)