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We need the most confidence to get started, but we won’t have that confidence until after we don’t need it anymore.

OH DAMN I know exactly what you’re saying, and the answer is this: Find outside ways of helping yourself build your confidence. You don’t have to do it by yourself. That’s how I got here. I would not be doing this if it weren’t for the people who encouraged me along the way. Sometimes, and I’ve noticed this with beginning artists, it’s hard to judge your own improvement or believe you’re improving if you don’t have people around who can judge for you, especially if you’re not used to judging that kind of thing for yourself.

So get other people to root for you. Look for safe and supportive environments. Ask people you trust for constructive criticism. Ask experienced artists, teachers, and people you admire and trust for advice, criticism, and support. Fandom communities are great places to build confidence because they’re very supportive. But even things like community drawing classes or art clubs are good, too, because there’s not a lot of elitism, and that’s what you want to avoid. If your parents are encouraging, then ask them for support, too. Deviantart, for all its faults, is a really good environment for beginners if you take advantage of their critique system and join some of their forums and groups.

The point is, get your stuff out there and practice allowing yourself to be seen and reviewed in a safe place. After awhile, you’ll have built enough confidence with the help of others (as well as the confidence you’ll build as you improve your skills) that you won’t need the training wheels as much. 

And when the real criticisms come your way (and I don’t mean internet assholes—I mean real grown-up criticism like whether or not you get hired, what kind of work you can get, etc.) you’ll have a much better infrastructure in place to face that stuff should you choose to. <3