As I've understood it, it's to be a self-made, independent man or woman.
Free to do what you wish, so long as such freedom doesn't impinge upon another's.
Ultimately it's about liberty and the ability to have your own stake in this life, like the old Homesteaders did. My mother is from a "third world" country, and they had months where they had to share a single meal between everyone in their family for the day.
She's attained the dream: security, independence, freedom.
Today I think it means what you make it out to be, post-modernity and all. I'm personally living it: not exactly rich, but free nonetheless as a freelance writer and webmaster.
I get to be at home with my wife and children, and work as I need or want to, for myself. Ultimately I'll employ others and share what I know, helping others to get a leg up.