Looking at it from a new powered but old glider lag, I've always erred on the side of caution when flying. I know what I can do and I don't try to do things that I can't. If something crops up that I haven't met before I'll discuss it with an instructor which may be enough or I'll do a dual trip and get it ironed out with them.
I can't go along with the 'most pilots are successful and therefore can afford to fly' line of thought either. Most pilots I know have to give up other things to get their two or three hours a month in. I'm not financially successful (the subject of money and the aquisition thereof really does bore me to death, as long as I have enough to get by), I measure success by other parameters; and by my own measurements I've had a pretty successful and full life. I wouldn't say that I'm arrogant either, most people who know me think I'm laid back to the horizontal. I am confident though. I also don't lose if I set myself a challenge, such as doing the PPL. Failure is not an option as they say.
An interesting thread, I wonder if there is a personality trait that pilots share other than the peverse delight in seeing hundreds of pounds a month disappearing in exhaust fumes?