Here's the first piece I completed for thesis: Sky Pirate Cap'n Gran! She's still one of my favorites, maybe because the character idea just cracked me up. It took me a while to get there (which you can see in the process sketchdump at the bottom of this post) but I wound up arriving at this silly smoking grandma whaler character. She's the matriarch of her ship (a zeppelin, in her case, because sky pirate, duh) and her crew is all her children and grandchildren and nieces and nephews and so on. She's talking to a group of them to get them riled up to go get some loot!
You can see in the sketch on the left, originally she was talking to a whole massive group of crew. I wound up cutting a lot of them out because they were just too distracting. I also ended up simplifying the space and bringing her closer to the wall, making that window much bigger. I did that to emphasize her silhouette and make things a bit less cluttered, as well as make it clearer that she's a sky pirate. Between the basic flats/shading in the middle and the final on the right, I wound up messing with the crew member in the front quite a bit. I got some feedback that people didn't see her arm as connected to her body, and also that her glove was covering up too much of Gran. I moved her all over the place, and finally wound up giving her tiny hands and a little noodle arm. I also rotated her head so it was more obvious that she was a person there, instead of that ambiguous hair shape.
I've got a bunch of process sketches and an explanation of how I got to the final design below - enjoy!