Don't be happy with where you are in your pursuit of anything, whether it be the pursuit of knowledge, skill, or whatever you can think of. What I really mean is, don't be happy to the point of passivity. You've got to be content enough to be incited to actively progress but not contented while under conceit.
The more I learn, the more I learn I don't know. Learning is a trade off. You give up the thought of "Well, shoot, I know pretty much everything there is to know about web development" for the thought "I know nothing about this, but I'm glad I know that so I can actually seek out the subject. I need to get goin'." If ignorance is bliss, then basic understanding is saddening, increasing knowledge is humbling, and ultimate knowledge is bliss on steroids. If you're afraid of failure, you're competing with no one. If you aren't, then you're competing with everyone in your field. That's why it's so intimidating. Once you accept your ignorance, no matter how talented you actually are, and progress humbly, you're going to get somewhere above the others and you won't even notice it until you get there.
When Ben Folds was asked what advice he has for new artists once, he said:
"Same advice that I think would have been true as long as there have been artists at all--you put your craft and your art first, you learn as much as you can, and you keep striving to be better. I'm never comfortable with people in the studio or people that I work with who think that everything that they do is great...it always bothers me. I think we all ought to be trying to get better and that's really the main thrust of it"
As harsh as it sounds, nothing you do is great. And as you become greater, you'll still believe this because you won't realize how much you've progressed. Let your content and self-confidence/self-assurance come from the joy of progress and the acquisition of new knowledge instead of the old.
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