Something about what I said a few days back has bothered me, and I've struggled to elucidate it since. The best i can come up with is that I always have something to lose in any given situation, even as a beginner. I do deal with sustaining the state of having plenty to lose - I just don't notice when I'm doing it well.
When am I more aware of what I have to lose? When do I worry about it? Why? And I also note that these two things don't always coincide - in fact, a lot of what I'm trying to avoid is the crippledness brought on by worries that I'm not aware of, or don't understand the motivations behind.
There are still logical fallacies in this, but I'm trying to work them out - it's one of those "man, your philosophy muscles are rusty" moments, as well as "look, you need to find more than 5 continuous moments to think about this at some point" times. Perhaps on the plane tomorrow.