Perhaps I could start working on the side as a college counselor. I am only 19, but I toured over 35 undergraduate universities and successfully applied to a top 20 school. That experience taught me a ton about how the process works and I am certain that you can "hack" the college application process.
One personality trait that has helped me in life I am extremely curious self-starter. When I want to learn something I completely immerse myself in it. I have done this a few times in my life. I did it with DJing, graphic design/ typography, finance, and more recently colleges. I think that the best way to describe this without talking to you in person is that I am able to talk about the things I am interested in such granular detail that it would raise suspicion of autism.
The reason I ask how to avoid the 9 to 5 is that many people, especially on this forum (I assume), are pulling it off. I am wondering how I can take advantage of my intense curiosity to do pull it off myself. I have 4 years to figure it out.