1.) The feeling that you have at 2 AM, when you finish a piece, and you are riding the creative high is your response to that out of body experience, the act of being a painter, what some referred to as visiting with a muse, but above all else, a beautiful thing to embrace, live in and realize as a goal. It is not fair to expect other people viewing your work to experience your work in the same manner. Distance yourself from the piece before you show it.
2.) If you want to sell paintings for $100 they will always be worth $100. If you want to sell your work for more than that establish that precedent from the beginning. If people do not want to fork over the $100, your work may not have reached the quality that you are aiming for. Do not despair. Keep your head down and work.
3.) It is never okay to forget the processes and rules that you learned in school. You are welcome to break the rules and ignore the processes in the creative moment, but realize that doing so will not be without consequence.
4.) Once you have "made" it, there are still many levels to attain. Try harder.
5.) Draw all of the things that you are too nervous to draw for fear of fucking up.
6.) Make your work. You are fascinated by a bunch of artists that you hold up on a platform as having "made it." They "made it" because they were confident in their own work and they had honed their skills to a level that allowed them to establish themselves in the art market.
7.) Selling art is business. Treat it as such.
8.) Make, sign, and follow contracts.
9.) Do not accept a project that you will not have enough time to complete without sacrificing the work that you really want to be spending time on.
10.) People are quick to attach the term success to money and celebrity. Whether you make a lot of money or not, whether you are well known or not, you can still be very successful. Determine your own goals. Live by them and have faith in yourself.