There's a fascinating post I read recently that talks about skill progression, and how it relates to your perception of your own skill level, your frustration, your perception of the skill itself, and your actual abilities in a skill. I could talk on and on about how this relates to this skill, or that, and how to maximize the upward trend. But I won't do nearly as good a job explaining as this image from the original post:

Isn't that amazing insight? You can abstract this graph to represent virtually any technical skill you can think of. Replace the word "painting" with "programming" or "playing chess". Almost any technical skill fits this progression model.