Similar Minds and Independence

I am like Siddhartha in the way that I go for what I want. He does not want to be a Bhramin like his father, and he will not let himself be pressured into becoming one. Siddhartha does not agree with how the learned men attempt to reach enlightenment, so against his father's beliefs he decides to become a Samana.
My father is always truing to pressure me to want to have a career in architecture, but I am more into things that have, well, less math and more... Art! I practice guitar and write songs hoping I could have a career in music, I paint and decorate maybe hoping to have a career in art.
Like Siddhartha, I am never really satisfied. He is rich and wise and learned, but he still is not... complete. I'm a very ambitious person who is seldom quite satisfied. 
In my opinion, enlightenment to Siddhartha would be to finally be satisfied, to be... full. Not full of empty wisdom, but most perhaps (just guessing here) purpose. To know that he can be more than a Bhramin's son and that he can be whoever he wants, not have to follow what he was born into.
Many people fell like they are forced into doing something when they have to follow their parents footsteps or are expected to be something since the second they can say "Mama" or "Papa" or "Towel"- whatever their first word might've been. Most of those people wind up developing an interest in something else, and some pursue it. What our buddy Siddhartha is going through might be just that, wanting to freely be who he wants. Wanting to find enlightenment in a way he sees fit.
Don't worry Siddy, we all want our independence.

Will Siddhartha 'lose' everything he has to become a Samana? the comforts and advantages of being the son of a wealthy and wise man? What IS enlightenment to this thirsty boy?