...And now you're trapped here, like the rest of us... muahahahahaa.....I didn't expect to be getting really into map making, I thought it'd be a one-and-done type of thing for me.
I think my 'story' is pretty typical - I started reading fantasy and scifi at a young age and I was fascinated by the black and white maps you'd find in 70s and 80s fantasy novels. I remember especially reading the Elric books in the early 80s and looking at that map and thinking "That is cool!" I'm a creative person (well, we ALL are here, or we wouldn't be here, amirite?), so it was kind of inevitable that I'd start to create settings and ideas and characters and then want to draw them. My earliest efforts were done on lined notebook paper, graph paper, that old dot-matrix printer paper with the feed-holes on the sides. Pencil, colored pencils, some ink. In junior high and high school I was in charge of dungeon maps for our game group. My most ambitious project was a huuuuge map done on a piece of large posterboard - I must've spent months drawing that thing.
Unfortunately, at some point after I left home, almost all of my maps, drawings, etc etc went missing. My parents moved often, so I imagine all that stuff just got lost in the shuffle somehow. Nobody's fault, just one of those things. Still sad though.
Anyway, I never lost the map making bug. When home computers really became a thing, and especially primitive art programs like MS Paint, I was like "f**k yeah!". The number of MS Paint maps I made was... legendary. Again unfortunately, almost all lost to the vagaries of Father Time and dead computers. I do have this late example though, from right after I got my first version of Photoshop. The map itself was done in Paint, the text and poor attempt at a canvas pattern in PS:
shieldlandsfinal.png
After puttering around with PS for a year or so, someone* saw my cave-drawing maps on DeviantArt and sent me an invite to the Guild, where I learned 90% of what I know about 'modern' fantasy map-making. This place has been an INVALUABLE resource for me over the years. Here's one of my very first maps done after joining the Guild:
FarasiaFinal.jpg
A lot of map-making is just repetition. Trying the same stuff in new combinations until you unlock something cool. Trying out tutorials until you become confident enough in your mastery of them to try your own spins on them. Building on the work of those that were here before. I don't think I'd be half the map-maker I am if not for Ascension and his awesome tutorials, for example. Unless you're some kind of mutant super-mapper like Max or J.Edward, there is no real shortcut except to do the work.
Hopefully that was of some interest and didn't bore you to death!
*I wish I could remember who that was. It was someone that was a Guild member at the time, but I have no idea if they still are...