Maybe 10 years ago a shoe factory bankrupted somewhere in north Portugal (cheaper Chinese products were starting to arrive). The thing got on public TV, and they were interviewing people. One of the women working there was desperate. What struck me the most was the attitude. She was begging for some entrepreneur to go there and "take care of them". The response was not either to take the issue in their own hands (and maybe become self-employed - "The American Way"(TM)) or demand the right to state support (which, by the way, she had and for at least two years - at an approximate income level of her salary). No, the way out, in her head was to beg for new masters (and note, they were making a ridiculous low salary with bad working conditions). Next to her was the union leader (which I happen to know), a hard-line trotskyist. We was quite comfortable with that attitude. That woman, might have a job today, but doesn't even know her rights and has the aspirations of being a slave. This is an attitude that I see on people around (starting in my own family), but that TV shot, by being so vivid, so desperate and so clear, stuck.
I contrast this with some very old anarcho-sindicalists that I know: born into poverty, minimal education. But they educated themselves, mostly in union created community centres with small libraries and such.
The only thing missing IMHO has been a non-toxic legal and financial structure to implement what are essentially Cooperatives of service providers in partnership with Cooperatives of service users. "Any economic unit can emit money. The serious problem is to get it accepted" Hyman Minsky
It's hard if you don't grow up with that mindset to understand how pervasive it is, how confidently you can walk into a bank or an office and feel that you have what it takes to work hard and take charge of things.
I have another friend who grew up in a huge mansion, and it's the same for him - he's very socially self-assured at board level, very comfortable hiring and firing people, and almost supernaturally aware of his own position in the pecking order and the relative positions of the people around him. He's not a bad person, but his education has left its mark.
If your education is working class, you don't get any of that kind of support or reinforcement. Yes, you can become self-employed - probably in a trade - but if you're of average intelligence and don't have any experience of banking, loans, taxes, employment law, and so on, setting yourself up with a small business is incredibly daunting. Turning a small business into a big business is even harder.
I don't have an answer to this. But I don't think it's just about getting the facts out and telling people that they have options.