In expressing my views on things like the Federal Reserve or the United Nations, I've been given labels like "cynical" or "pessimistic". I don't think that this is a fair characterization in the sense that I don't wake up thinking about how much the world sucks or how nothing I do matters. Quite the opposite—I recognize how bad lots of things are, but I think that each of us can still choose to continue in spite of these obstacles.
Analagously, let us suppose you have an old, slow computer. Maybe it has crashed many times while you were trying to do work. You can descriptively talk about many of this machine's shortcomings and how it fails to fulfill many needs you have. Likewise, you can reflect on how it is "good enough" for some things you do and think about how you can use it more effectively, even if you plan on getting a new machine eventually.
I think about lots of things in the USA in a similar way. I'm not "Anti-USA" in that I've lived hear my whole life and I have enjoyed many things because of the institutions that are in place. However, I think that it would be wrong to cling to many of the myths/narratives that are used to "sanctify" our present order.
Caring about a place and its people means being willing to hear criticism—even if this criticism means that things you may have invested in are not as good as they may seem. For instance, I've benefitted from having a college degree. Writing this on a piece of paper probably makes applying for many jobs, getting credit cards, and so on easier than if I didn't have this thing. It would be wrong for me to fanatically defend the college system just because I benefit from it; if there are legitimate criticisms of higher education I should not steer away from these just because I am in a position to benefit from the present way things are.
If I make a bunch of money off stocks, I shouldn't take this to mean that I'm super smart or deserving either—the system is in a certain way and I steered my boat to exploit the winds. But this doesn't mean I've "earned" or "deserved" anything.