@Shandi - I was always told that I should go to university "because it's a natural fit for your academic inclinations". I was told to study what I love, not be income-focused. (As a consequence I studied two years of Anthropology and History, then dropped out with student debt equal to my yearly income.)
My parents never once mentioned skilled trades to me. They did teach me about job interviewing, but nothing was said of networking, climbing the corporate pyramid, negotiating salary, etc. As a consequence, I've spent my working life hopping between entry level jobs. Right now I'm caught in the call centre trap, and looking to get out of it, while paying off the debt.
There is a larger company across town that will pay 50-100% more for essentially the same job I'm doing now. Three of my co-workers have actually left my employer to go work for them. I'm in the process of interviewing for a position there, but, man, is this surprisingly hard to do for me!
I have also debated becoming an entrepreneur. I dabbled in that a little while ago and really liked some things about it. There were some bumps, but I'd be willing to modify it and give it another go with a better business model if this job change doesn't work out.