First, Ride: Debbie Millman Finds Her Cowgirl

Why do we stop experimenting early on?

Why do we walk away from the passions and the possibilities that might provide us meaning and income later in life?

Those thoughts from Jonathan Fields form the subtext of this fantastic video with IdeaFestival 2014 speaker Debbie Millman, who talks at length about her life choices and struggle with fear and self-doubt.

She says she "experimented all through childhood," trying on various characters like cowgirls. She loved "doing lots of different things," and it was in college that she realized that design could be a career. She graduated college with skills in design layout "and paste-up," and goes on to describe her post-college years as a decade-long time of decision. But, she says, she was "afraid to write, to paint," to create "things that didn't have a commercial value," and consciously chose a path that would provide her with security.

The first summer post-college, "I made every choice... based on fear."

Listening to Millman and Fields discuss the hold that fear can have on creative expression and meaningful work, I was reminded that creative, accomplished people, whether they work as entrepreneurs or in the arts, never eliminate fear. They just cultivate a skepticism about their own insecurities, the better to get on with it.

Jonathan Fields, coincidentally, is the author of the "Uncertainty," a book about how self doubt can cripple, so the conversation he and Millman hold is full of hard won wisdom.

Catch Debbie Millman and the other terrific people at IdeaFestival 2014 - many more speaker announcements are coming very soon! Festival passes are on sale now.

Stay curious