I'm a fairly well-organized digital pack rat so, you guys... I actually have THE FIRST EVER digital drawing that I did. This is from the first day I got a tablet and couldn't make eye-hand coordination work quite well... It's from around 2006.

Then this was the first one I completed (I'm pretty sure?) a couple weeks later. I didn't know what multiply was, or couldn't use layers that well either, so I just drew on top of a sketch I scanned lol...
Fast-forward to a few years later, this was in 2010-2011... I didn't really understand how shadows worked so it usually took me hours with the darn airbrush to get the final "look". And! I discovered ~CUSTOM BRUSHES~
This is one of the first drawings of Dot that I did, probably around 2013-ish. She was actually a young adult back then.
And another piece - of a different character (Peppermint) from my novel. You can see I still don't really know how shadows work.
Aaand now for the more recent (+ ~3 years of dealing with a nerve injury during which I couldn't draw) 
Dot!
Peppermint!
Random blonde(ish) guy, to compare to the older ones! I'm starting to sorta figure out shadows, haha.