I recently bit the bullet and picked up an iPad Pro and Apple Pencil in hopes of simplifying my illustration process a little bit. I’ve always found it clunky to move from paper sketches to digital and since getting the iPad, I've been able to save some time. Yay technology!
I used Inktober as an excuse to learn how to actually use it, and each day created an image using Procreate. This turned out to be a great way to learn the tool quickly and make a bunch of mistakes without it affecting the workflow on an actual real life project.
The constraints I set for myself were that the drawing had to be black ink only, fit within a square, and the background colour had to change every day from the day previous.
It was actually super gruelling and I wanted to quit all the time. Don’t think I'll be as ambitious next year.