I like the story HighWing. I have known some people like that, capable beyond description. The dangerous ones are the ones that don't know that is the case and encourage others to do the same as them.
If nothing else this thread has brought out some old aviation cliches for dissection and discussion. I think this one has been said or paraphrased at least three times on this thread alone and it is another one that I have not quite embraced. Here is the Oxford dictionary definition of bold:
bold
/bōld/
Adjective
(of a person, action, or idea) Showing an ability to take risks; confident and courageous.
I have a coffee table book of aviation quotes titled Slipping the Surly Bonds which I highly recommend. One quote "There are old pilots and there are bold pilots, but there are no old bold pilots" is of course the one I am talking about now. I would say that by the very definition of bold there are ONLY bold old pilots. Any pilot that was not bold I would not want to fly with. Another quote from the book is "Courage is being the only one that knows how terrified you are." That is a character trait that I expect to see in a pilot. Other wise when that punctuating "moment of stark terror" arises, the not bold pilot will lose composure and possibly not make it out. All of us are of course confident. How could you ever solo if not? You just have to keep an eye out for over-confidence. And as far as taking risks, I will once again point out that this community is a collection of people who think a good hobby is to go burning holes in the sky in an airplane that they built in their garage!
I think the intent of the saying is probably solid, but with a poor choice of words. There is no need to take excessive risk all the time. The more exposure you have to periods of flying with no out the more you increase your chances that when something goes wrong it will be unrecoverable. But to imply that risk should not be taken is ridiculous. I would say that bold was picked to be used in that phrase because it rhymed more then it made sense, which implies a Safety Officer thought of it. And probably a military one at that.