read pick-up materials like "The game", you'll be surprised to learn that even some average people who tried hard to overcome their fear and negative side can become winners (well, in term of winning women), but technically it'll help you more than that, you'll learn how to become alpha, the type of ppl who loves taking risk, like approaching women without the fear of being rejected (just like doing startups). the point is you need to do risky things, challenge yourself, put yourself to the limits, then you'll feel rewarding after all those efforts (doesn't matter much if you fail or not). Hope it helps