In regards to debt and money, I wrestle a bit with feeling hopeless and kind of like a victim of my background and past choices. Funny -- I don't usually think of that being a struggle for me. Beyond that I have a great background and better mentors than most people I know, and our debts are not large by US averages.
I think part of it is that I'm coming to terms with reality. I wasn't tracking the fact that even with school loans ("great" loans that they are), we could end up paying twice as much as we borrowed easily. Most people have encountered this grim reality long before now in their lives, but we've gotten a lot of help, have lived pretty simply and have been privileged to not have incurred many debts that would have taught us this before.
I understood the theory before, but looking the debt in the face daily is a little different. Like with anything -- theory and experience, the idea of the thing and the experience of it are profoundly different -- something difficult for a dreamer/starter/futurist (using the last term loosely) like me to remember.
So, out of all this there are two things that are taken for granted in US culture that I don't like and about which I wonder whether things really need to be this way:
1. We think it's normal to pay back twice as much as we borrow.
2. We either expect to rent all our lives or to be paying off a house for most of it.