Sean J. Leith
One big thing I will do is, if I'm unsure of a landmass or haven't quite figured out the story, I'll draw a random nation/continent. i throw some dots on there with random city names, put lines for roads, put some mountains or forests, and so on. It's completely random, but I've had this method work several times for inspiring a character's journey, their story, culture, and more!
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