I'll add in why I dropped out of college (current software engineer making six figures).
My dad made just enough money to get us past the point where Pell grants were denied because of my Dad's income. Unfortunately, my family still couldn't afford it and I was exceptionally weary of taking out 150k in student loans. The most they could afford to offer me was $200/month in rent. After a semester, I just dropped out and got a job at a local ISP as a software engineer.
Would I have went to school? Absolutely, but I couldn't afford it. As a person with Aspergers, it would have also been exceptionally hard for me to work /and/ attend school full-time. I tried that and it didn't work out.
I still have dreams of getting a doctorate. I love school and I love learning. I love being in class and attending lectures. Maybe when I can afford it and do just that, I'll do it.
As a person who graduated three years ago, the education system (even to an upper-lower/lower-middle class kid) is absolutely disheartening and dream crushing. Intellectuals don't speak of social darwinism, but their organizations, fiscally and structurally, still do. I will always feel inadequate for never having achieved a degree that all my friends will soon or now have.
I learned to only rely on myself, though. It's turned me into a very mature and responsible 21 year old. It still feels like I have no idea what I'm doing, but I'm working on it.