My ego thanks you

. No, in all seriousness, I appreciate your kind words.
I guess the difference that concerns me is that people here are usually asking for help and most already have some notion of personal responsibility.
What do we do about those people in the 'real world' who just complain? Or who, when they ask for help, defeat every positive thing you say with more negativity and victimhood? Do we just keep on living the best way we know how and hope they will see it? I really would love to do as much as I can to help so long as I don't sacrifice my own positive outlook.
For example, I have a friend who has always worked kind of low wage, low status jobs. But he blames the problems he has there on the boss, coworkers, etc. I have encouraged him to go back to school for something he enjoys, but then come the excuses: I don't have the money, I will never pass math so a degree is out of the question, how will I work and go to school...I have to pay the bills. Even if I have a positive answer to every question along with an offer of assistance with the details, there's always some other reason it won't work.
What could I say or do in a situation like that? Is it really just about living it as an example? Because I tend to be told I've had it easy and that everything I have was handed to me (which is so ridiculously not the case).