Pushing ourselves beyond the comfort zone most likely reveal ugly truth about ourselves that our ego have been trying to protect ourselves from. I found that what I thought were world's injustices directed at me were really my own insecurities and sheer laziness; or my notion that I'm a nice and considerate person is really sour grapes that I didn't have X; and in the position of getting X, I could be as selfish and manipulative as the next guy who has X, whom I previously vilified. Stepping out of comfort zone reveals who we really are and sometimes the truth is ugly.
In all of these things, you strike a balance and find what is moral or healthy--that is part of the journey. I wouldn't want to use possible straw-men morality as an excuse for continued ineptness. Like white hat security pros, you can know how to do something but choose not to do it.
No, I haven't completely achieved all of my goals although I have gone very far in all of them. But I'm not as anxious about them nor about admitting on my shortcomings on my goals in public; like in programming, at a point you develop a sense of confidence that even on a long programming project, it's only a matter a time that you will finish it. It's just a sequence of iterations of coding & debugging.
How did programming affect my life? It made me a nerd with inferiority-superiority complex who on one hand views average human beings as automatons who let their sense of social insecurity get in their way; and who on the other hand is insecure himself, requires constant social re-assurances, stroking of the ego and (most importantly) sexual gratification. And for that, I'm eternally indebted to programming.
I made myself go back to university when my first experience was not successful, I'm now on track for a great degree. I am in the process of chasing a few business opportunities, and I'm putting myself in the position of a marketing man. This has already lead to some promising leads. I also tried to be a bit more open minded and non-judgemental, and socialise in ways I didn't previously, and I made some great friends as a result.
Your life is in many ways, very much in your own hands.
I view my "self" as fluid, and whatever I want me to be.
You're not supposed to be awkward and uncomfortable just for the hell of it.
-public speaking
-asking women out
-learning to dance
-socializing/making friends
-lifting weights
-starting a business
-doing sales work
-learning to program
edit: The vast majority of these made me very uncomfortable and awkard, not "a little".