The ability to ask a question that goes unnoticed by everyone else is the mark of artists, entrepreneurs, and basically anyone whose goal is to add something to the world that isn't already there.

Also most of the questions a person can ask that go unnoticed by everyone else, go unnoticed because they are stupid questions.

These things are not contradictory and as long as you can have a sense of joy and humor about it and ask the goofy questions anyway you're ahead of the game. The follow-up step is to have a relentless eye for quality combined with a soft appreciation of what others think (appreciation is not fear) and when you find an idea you think is particularly darling you then demand that it be the best, most useful, most presentable version of itself. Combine those things and you're golden.

My peers in graduate school always knew me as someone who was a slight oddball, and who was always captured by some new flight of fancy that he (likely) would not follow through on. But I had enough good flights of fancy that I could select the best of them and when I did it left other people impressed.

Soo.... not sure what to say here, in terms of advice? You should write the piece on the Camino, and send me a message when you do so I can read it. You're a writer. Nobody will look down on you for your misses. Many will find them endearing. And every now and again you'll find something that lies on the sweet spot between conventional and creative and you'll get a big hit.

Leaders are just oddballs who walk away from the crowd in a very specific direction -- forward.