They won't try because the consequences for them could be disastrous. It's not even about how much money is in your bank account, though that obviously helps. It's more about how stable and reliable your support structure is. Without that the consequences of failure can be devastating.

I think it's dangerous to encourage people to gamble their lives on a low probability outcome if they don't have a strong network of friends and family to fall back on. If you have that, then go for it, but don't pretend that anybody can pull themselves up by their bootstraps and do what you did (I'm using the royal you here). That attitude is what the criticism is aimed at.