It is much more straightforward to illustrate that an individual is failing a system than it is to illustrate the system itself failing the individual.
This is because a system sets the very problem domain for a person to "fail". By virtue of being a system, it is trivial to point to it and say "where" and "how" the person is failing inside it.
People are not so easy to describe. A person is not a simple system. Their needs are not so easy to point at and say "where" and "how" a given system has failed them. Each person is unique, and there are hundreds of millions of us all interacting with one system.
But that complexity is in everything you are asking of people here: What's does it mean to "lift yourself up"? What are the circumstances for "risky behavior", and are there really better options? Is the behavior a problem or result? These questions are all fraught with complexity, because people have complicated needs and complicated circumstances.
What we really need is to set a new problem domain: the needs of each person. But suddenly this becomes some vain moral debate: isn't it selfish?
It is. So is a system.
But what if a person's needs are to be taken care of without having to work hard themselves? Isn't that unfair?
It is. So is a system.
Our system demands we ignore such edge cases, and wave them off as moral failings: the person's fault: but what gives our system the right to say so? After all, this is just a system: it isn't God! We made the damn thing! It doesn't get to tell us what is right and what is wrong. Yet we let it do just that with every person every day.