Doing something out of your league, to me, is greatness not because it is something that people would kill for or because it proves how awesome you are--in fact these reasons are reasons not to do it. Doing something out of your league breaks the shackles of what you think is possible not for yourself--that would make it too conditional, but what you think is possible in general.
Here's the logic. In a career, yes it's people who are skilled at something and get in the proper lane to then have their hard work promoted. Yet, the real work is often in stomaching people and situations you don't like doing things you don't like to do in order to succeed AND/OR taking a HUGE risk with a huge fallout potential. In your finances, it's something that requires a lot of discipline in not getting yourself in debt now so that you can afford a cheaper place now and buy something later AND/OR investing in a risky venture that could make a ton of money (most businesses.) Now with a career or money, if a person majorly succeeds what do we think? "oh my god he got so lucky he's like a powerball winner. i wish i could be so lucky."
Same thing with girls.
Getting girls that are "out of your league" is not a really sexy process. It isn't about buying a sports car, having rock hard abs, being famous, being gorgeous, it isn't even, in the end, about being the life of the party. Those things help, certainly, and the path can be brutal if you don't have any of those things going for you simply in terms of getting their attention. However, it is much less sexy than that. It is powering through the misery to reach the end of the tunnel.
Only Approach Girls Out Of Your League
If it's important to you then let it be important to you. Here's a little theory that i've been playing with--women actually do enjoy being worshipped. This does NOT mean they enjoy being worshiped so that have sex with the guy--this would be enjoying being manipulated. What i mean by this is they enjoy being treated like queens. Well, it's a hell of a lot easier to treat a woman like a queen (with no ulterior motive behind it) when she looks like a queen! In this way, really all men could desire a girl out of their league but don't similar to how many people look for jobs that are realistic instead of fantasy jobs. The ones who go for it simply have more hope and delusion often times becomes reality for those who are committed.
Learn Hot Girls Through Being Around Them Rather Than Theory
Theory is a mindf*ck which is funny when you think about it. There are a million-million micro interactions that go on every time you say hello to someone. you couldn't possibly know all the inner workings. A little is good but honestly most is unneeded and harmful. You won't truly know what you're talking about it until it's so ingrained in you through experience that you wouldn't really know how to articulate it. It's like being great at drinking water. It's so simple and straightforward it seems silly to claim to be good at it. It just is.
Barrel Through All The Crap But Realize It's a Marathon Not A Sprint
Barrel through rejection, flakiness, craziness, etc. etc. etc. You'll have girls who will insult every thing flaw about you that you didn't even know you had. You'll have girls who'll say fuck me in a stall in the men's room. It's a lot of crap and a little greatness. The thing to remember though is that it's a marathon not a sprint. You want to pace yourself so you don't get discouraged. You want to give yourself props whenever you even have a nice conversation with a very hot girl. You want to build the reality that hot girls are gettable by you. And, in the end, you simply want to date a girl who's out of your league.
By the way, I'm not exaggerating with out of your league. Don't see limits. Only possibilities.