Obviously, for people who have no money or the means to produce it, will find that money becomes a necessity.  But let's ignore these people in this particular conversation because they are a rather extreme group which you don't have to deal with yet.

It's simple, just have the courage to make up yuor own mind and not cave into pressure or expectations of others when their goals are incompatible with your own.  You just have to learn to be callous and uncaring of certain things that hinder your progress.

There's an operating point in a graph between financial gain vs. job satisfaction, and a graph between financial gain and screwing people over.  You just have to locate that point, make your decisions based upon it. 

People like my younger brother do this easily.  All you have to do is be selfish and exploit/manipulate all situations to yuor advantage.  That way, you know when you have enough money, you know when you're going to leave a job despite the fact that people have become dependent on you etc...Basically, it means you're not afraid to exercise your "free" choices when they present themselves.  People like my brother aren't worried abuot throwing themselves into ugly situations, like doing a job they hate just for the money, cause they know they can leave it whenever they want to find a bigger and better job when it comes around. 

The executive director and managers in engineering firms that you mentioned probably have MBAs; otherwise how did they obtain the skills and qualifications to manage a business? Here we've struck a key point: how can those with sub-par GPAs even get their feet into the doorstep of a good MBA school? Granted that renowned MBA schools are willing to overlook a below-average GPA if the applicant has a stellar work record, asking them to accept the GPAs given out to many students in U of T's eng department is still pushing the envelope a bit too far.

Thought you might find this funny.. was reading an article from The Toronto Star and came upon this paragraph:

"Unable to find a use for his economics degree from the University of Toronto, McKell chose to follow his interest in race relations and landed a job with the school board encouraging immigrant families in the Parkdale area to become involved in their children's schools."