Do we really pave the paths of our lives?

Do we? As soon as most of us are born, we're thrown into the hectic schedules of everyday "normal" life. We get potty-trained, we learn to speak, and we go to school. We see people in almost every single movie who find their own way, and discover who they are. They defy the norms, and are ultimately successful. But is it really possible for an average person to "change their stars"?
It is extremely unlikely that people who stray off the beaten path will become successful. Of course, that depends on what a person's idea of successful is. My idea of being successful: ending up at 60, and being able to say that I am happy with my life. Though it may be considered superficial, I want to have luxurious life with ample money. For that to be realized, I either need to become a SUPER creative person (which is unlikely considering my current inability to come up with ideas for even a science fair project), or I need to have a good job. Good jobs do not just drop out of the sky. They are achieved through hard work and conformity. I need a degree of higher level education to have a shot at making the kind of money I want to make, and to get that degree, I need to stay in school for quite a while. I do not have the resources to drop out and still be successful. If I try to make a wholly independent life away from the social and economical norms, the odds are that I will fail.
Which brings me back to my original question: Does an average individual have the power to make his life his own? Tomorrow, I may decide I want to move to Japan. But is that really feasible? No. First off, I don't speak Japanese. Secondly, there is no way I could afford to go live there. Lastly, I can't hope to make an ideal life in Japan. While I may enjoy the technologies available to me there, I will not be able to afford them for a sustained period of time because I will lack the ability to make the money I need to do so.
Money seems to be the central issue here. Granted, the human race can't eradicate the need for money. Without it, people would inevitably become lazy. Don't deny it. How many times have you heard this conversation: "Ugh, I hate my job!" "Then quit!" "I can't! I need the money for rent." It's all about the money. If every single person did their jobs without being offered money, society would be perfect. But this is an unattainable goal, since there are plenty of jobs that people just don't want to do; they will have no reason for doing them if they don't need the money. If goods were just handed out for no charge, members of society would not take the initiative to work, to create, to invent, or to produce. The consumers would overrun the producers, and ultimately society would fail because people would run out of goods. So, in short, money's important. It keeps the world moving.
Unfortunately, money is also a hindering factor from the ultimate goal of pursuing our dreams. I don't think it is possible for us to shape our lives the way we want them to be. It's actually pretty unreasonable. The odds for failure are extremely high, just as economic pressures are. The ideal is a nice dream, but it is ultimately unrealizable for the average person.