Do you mean battlemaps or area maps?
Gotta say, I don't worry about it. Maybe I'm a bit cavalier - but all it has to do - for me - is to serve its purpose, which is to further the fun. If it doesn't that job, it's a successful map.
Area maps... I'm ok at like the large scale view of a continent say... but once I get down to smaller local view... things just look weird. I guess I never feel like I get the scale correct or something.
I think I just need to step back and give it a day or so, then come back to it.