It's a common thing. I would say, just toss something down as a thumbnail. Random scribbles sometimes help. See what you can pull out of that. I also like tossing tracing paper over my drawings, and redrawing things. Sometimes I can add new things, get a tighter pose, etc. Just keep drawing. 
You're on the right track! Ended up doing a bit of a draw over again. In that reference image of TGMD, I would look at his pose. They are really pushing it. Of course, that is more whimsical, but the same rules apply.
I also shortened the extended arm as it was too large.
Hope this helps.
So I ended up giving this a bit of a draw over. I think the idea is good, it's just the silhouette needs a bit of tweaking. I gave him more of a streamlined look, since he tends to be lanky. Also changed his pose, since it was a bit confusing if he was confident or unsure of himself. Then I also changed the hand, as it was difficult to read before.
Hey all! Sorry for the delay, work has been crazy. Thanks for the feedback! You guys were right about Red, so I ended up changing her.
The lack of real "pro" applications is also a turn off. I would love to run OSX, but iOS.... no thanks. It just feels like a huge step back. The stylus also doesn't have any buttons on it, so choosing brushes/etc, requires more movement.
Looks okay. A Surface Pro 3 is cheaper, and runs windows. Also they don't mention palm rejection, so that might cause some issues. Every person in the video didn't have their palm on the screen.
@Thrace-Shirley-Mears Thanks!
@DanetteDraws good point! I'll make that change!
@Rob-Smith Thank you!
I wanted to do some character designs for Red Riding Hood for my portfolio. Here's what I ended up coming up with!
I have also designed a home for grandma, however I am not too happy with the colours, so I'll probably finish that up this weekend.
Thoughts/Comments?
They're good. However, I would probably focus less on the rendering for right now, and more on the gesture. Draw quickly, and keep it simple. People are always moving, so you want to be fast. When I'm drawing people on the bus, I have about 5-10sec, to grab as much as I can. After that, I just add details. Keep it up though!