Sometimes working on maps makes me crazy
Usually when I have to redo something big.
For an alternate history map, I couldn't find a good reference for the western hemisphere in the right topographic style. I tried different ones, but they were too warped, too small, too simplistic, or far too detailed and fancy to be useful.
And for my fantasy map, I have had to redo the coastlines and mountains when I switched to a higher resolution to eliminate the annoying blurriness. Then I had to redo the trees a couple times to get the right type of look. Then I spent a long time drawing tons of tiny trees. Then I drew the cities and found that I needed a smaller scale, and redid the cities. Then the trees were too big, so I needed to break up the tree layer, shrink them and draw in a lot more trees.
I think I am torturing myself a bit with the totally hand-drawn aspect, but I really prefer the look. I'm a bit picky, and I dislike seeing the exact same symbols all over a map that is supposed to be hand-drawn. On the bright side, the craziness made me take breaks, during which I developed the world quite a bit. I have many more ideas for cultures, religion, institutions, militaries, architecture, and magic.
I have now grown attached to it, especially the cults, and intend on making it my definitive fantasy world.