Overcoming a Fear of Failure

Everyone faces obstacles. The question is how you deal with them.
The most difficult are those we make for ourselves. Recognizing what these are is great, but then how do you overcome them?
I've read my share of self-help books. As an ambitious person, I need to continuously improve myself however I can. It's ironic then, that my biggest obstacle to success is myself. It's more ironic that so few of these books actually give a road map. They often make their money on talking around things. The authors themselves, it would seem, haven't quite figured out these answers themselves. Needless to say, it puts me in a bit of a spot. Let me explain.
I've got my purpose and a bit of direction, I even have a killer skill set, you're wondering what's stopping me, right? It's the dumbest thing ever. And it's doubly ironic, considering my drive.
I have been afraid of failure for the majority of my life.
Historically I've been paralyzed by this fear. I can blame a genetic predisposition of worrying, critical family members, and even the political requirements my parents' positions placed on my brother and I. Still, it doesn't matter. It's my problem. If I don't get over this moronic obstacle, I won't go anywhere, because I won't try.
If I think I won't be good at something, I would rather not do it than risk humiliation. Generally this dreaded humiliation would come from my perception, as opposed to others' judgement. It's stupid. It's annoying. And frankly ridiculous.
It's ridiculous to fear failure and to let it paralyze me for several reasons.
First, it is impossible to be an expert at everything. Someone somewhere is better, just as someone else is worse. Who cares? And if I don't try, I can't improve. So even if I suck, I will never get better because I'm unwilling to practice.
Like I said - stupid.
Second, it is impossible to live when one won't try. Literally, this fear can prevent a person from experiencing life and fulfilling his or her purpose. That's about the worst thing I can imagine - not fulfilling my reason for being.
Third, nothing is gained from nothing. It is impossible to be successful when I don't try to be successful. This is an axiom I have taken to heart in many aspects of my life, yet I have hesitated to apply it universally. For example, when I was still dating, I would ask any guy out because I couldn't lose something. If I didn't ask, I knew he wouldn't date me. If I did ask and he said no, I was no worse off.
The fear comes when you perceive loss. Loss of pride however, is so much smaller when compared to lost opportunity.
Finally, fearing failure is moronic because failure helps us learn. When I was shamelessly asking guys out, I began to understand why people did the things they did, and the kind of person I really wanted to be with. Learning made things better, so then I could get it right in the end.
So how do I get over this idiocy?
My plan is brazen confidence. Yes - shameless, ridiculous, try-anything-to-get-it-to-work awesome is my plan. And by the law of numbers, it will work.
For those of you who know me well, this might be frightening. The idea of Alexis with unreasonable confidence sounds larger than life, even to me. It might cause the destruction of cities, but I will risk it. I have come to a point. I have nothing to lose. If I don't fulfill my purpose, I know I will regret it. If I am not successful at this, I may be found drunk in a gutter for the rest of my life. There is no other choice. Literally, my soul is on the line. When a person gets to that point,  what's a little failure? What does it matter anymore?
This is why eventually the world and nearest stars will be mine. It's that, or I lose myself. There is no between. So now I shoot for the moon.
Ready. Aim.  FIRE!

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