I've never been a very strong painter or color illustrator, so most of my experiences involve admiring painters/illustrators and their work from a distance.
About ten years ago, I bought the cheapest, no-frills, entry-level Wacom digital tablet on the market for about $40. The working area is about 3" x 4", and the pressure sensitivity is nil...it's so difficult to get a varied line width out of it that I've given up on trying to ink anything I've scanned in. Despite all this, it's provided me with a starting point now that I've finally begun to seriously study it.
After many failed attempts over the years to do anything with it, recently I started looking for tutorial videos on YouTube on the best ways to paint digitally. One artist in particular (Architectus777) was very good and thorough with his tutorials, covering all steps of his painting process. Additionally, he covered in detail all the brush sizes and settings in Photoshop, which I've found is imperative to get any kind of results out of the process.
First came the handful of failed attempts at finishing anything, discouragement, etc., but after a couple of days of practicing with the tablet I was able to get the hang of the technical aspects. There's no real easy way to blend colors in Photoshop, so learning how to pick up colors quickly with the eyedropper keybind is very important.
I managed to finish a couple of black and white pieces that weren't great but were pretty good progress for me. There's always a feeling of relief and accomplishment right after I finish a piece, but after some time passes and I find all the areas that didn't turn out as well as I wanted, I tend to get a bit down. I suppose I get frustrated that I'm not learning fast enough...
Over the weekend I was able to finish a simple, fleshed-out color figure that was also a pretty good mark of progress for someone who hasn't done much color work over the years. At this point I'm pretty excited to keep learning so I can get better.
Now that I've got some experience learning the tools, all I have left is to merely learn more about form, composition, lighting, texture, brush techniques, layering, anatomy, perspective, tone, and brightness/contrast, and I might become a decent painter. Ha ha.
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