One of the ways recommended for strengthening your skills is to start a project where you draw your subject repeatedly. There are a ton of projects on the Internet where artists pick a subject and commit to drawing or working with it for a set number of days (30 days, 100 days, etc.). I am starting a 100 day project for portraits.
Will I draw a portrait 100 days straight? I hope so (but probably not). But I
will challenge myself to draw more portraits. The catch: DON'T stay in your comfort zone. Do something
completely different, mix it up and see what results. You won't learn anything if you keep drawing/painting the same way.
Here is the first in my series. No I won't post every single one. But I really like this first attempt. I used the half-blind contour technique. You get a reference photo, place your pencil on the paper and slowly draw what you see. You
only look at your paper when you have to move the pencil to another place in the portrait. Then continue with the drawing.
You end up with wonky lines, strange shapes and a completely different look than what you normally draw. I would never draw that wonky shoulder bump or the shape of her back intentionally this way. And certainly not the lips misshapen like that. But I LOVE how these turn out. You then look at what you've got and work with it. No erasing!!
For my next portrait I'll use the blind contour. You can't look at your paper AT ALL after you begin. It ends up really distorted and usually pretty cool.
So that's one of the projects I'm working on. I really want to challenge myself to see what I can come up with that is totally different from my usual way of working.