Zack,
I have to fully agree with what the guys said. If you work for yourself you have to do all of the work as well as finding the next job and advertizing etc.
I work now as a computer technical lead training people how to use the computers to build systems. I have teams of people that I mentor and guide and I enjoy what I do. They key thing is enjoying what you are doing. I tell people I am going to "play work." If you are good at what you do the rest seems to follow.
I also enjoy playing "jamming" with groups and people. Fun stuff only. I have played for weddings and that scene but not for a living. I have worked as a professional magician and entertainer for over 30 years and that has been fun and profitable but it has the same challenges as listed above. It is nice to be able to start into it with a backup plan.
The college I went to had a school of music as well as computer science. A lot of people thought I was there for the music. The computer part was easy for me so, as a lazy person, I just went with it. Since you are a bit younger than me and at a pivotal point in your life I would suggest you try a few things out. While in college I performed at parties, around town, every chance I could get. It paid for all my books and spending money. I still feel what I did was the right decision for me (but only me). Only you can make that kind of decision for yourself. I would highly suggest you try a variety of things out first before that kind of career planning. Remember that the wonderful thing about it is you can change your mind later on.

"Find something you love to do and you will never have to work again."
This basically means if you enjoy what you are doing it really isn't work.

I have a cousin who says: "Man plans... G-d laughs."

I hope some of this makes sense and helps you a bit.

Good luck in whatever you choose.

- Brian