Hey, B_C, I would hasten to point out here that the times are changing. I work in the finance industry at a pretty advanced, let's say, mid-level position. My immediate bosses in the past years have been assistant vice presidents or VPs and up. This sounds like I'm a pretentious douchehole talking out my ass to sound important, I'm sorry, and I'm not. So anyway, in this position, several of my co-workers have not had college degrees. They are older (50s) and they have essentially hit the ceiling, partially due to their lack of degree(s). I can say this with certainty because I am in my mid-twenties and I was hired into this position precisely because I had a college degree. Yes, that's right - I'm mid-twenties and I'm starting out at a place where other people are ending their careers because of one stupid little piece of paper. My degree isn't even relevant to the work that I am doing! But there is a big push to get these mid-level degrees filled with people who have diplomas, as opposed to the people who have been entrenched in the system for 20 years, worked their way up to good earnings, and are now at a ceiling. In all honesty, that is that CEO of the company you know. He has managed to work his way up during a time in which college degrees were not so important. Think about it; he was probably part of the 'trench warfare' in that company in the 80s, when a college degree was much rarer and a more significant deal. I highly doubt that you would be able to replicate his sort of success today with the ubiquity of college degrees and the growing requirement of employers that the people they interview have this requirement.
I understand what you're saying. I'm so gung-ho about my dream that I am perhaps letting my vision of the future become jaded. I'm not necessarily allowing for the possibility of joining the system to come true. In part I do that intentionally. In not preparing for that situation I'm even more determined to make my dream a reality.