Really great talk! I've never really been in a system, at least not in one that was "functioning" by its own definition, and especially not in the way that I really felt I was a part of it - but interestingly I've often envied people who are in such a system as religion, if they are in it fully convinced, because I've often felt that it would be comforting and in some ways an "easier" life.
For a very long time I've tried to be a part of systems, I guess, but none felt right and I've finally stopped trying not too long ago. At which point I felt that I had found the place that is right for me.
I am actually not sure what exactly made me question anything from the very beginning on, but maybe the reason actually was that there never had been a functioning system, that I've therefore very early questioned concepts of family (total mess so what is it good for and why I am here), God (not baptized, but read the Bible out of curiousity when I was seven or so - nice stories, but the concept didn't make sense), later education (especially the part when the own process of thinking is replaced by only quoting "some authority in the field", here probably Niklas Luhmann), and so on. Of course, I'm still part of systems - like the society I live in - but I feel more like an observer. I do very much like thought experiments to challenge "in the box thinking" of any kind, especially when it comes to decisions that are socially not only accepted, but expected, with which I've had some experience, e.g. a woman's decision to not want children (and be happy about it). I've learnt a lot about systems (and who "runs" systems) there.