If one is thinking about these experiences as "right" or "wrong", they have certainly failed.

Uncomfortable, sure. Experiencing the dark night of the soul is not meant to be comfy. It can be rewarding though. Sometimes it is merely insight into our physical and psychological make up though. I don't care what kind of adventures one gets into but if you start getting extreme with them, you're eventually going to experience some really sketchy, uncomfortable, and even life-threatening situations.