I think your thesis is well-made: a relentless search for "the point" hampers creativity, perhaps strangles it. Jobs is a wonderful case, and his inspiration by the calligraphy course is memorable.

I remember wandering in the stacks of many libraries, lost in distractions that became my life - like "grass-style" Chinese writing.

I would add a hopeful addendum: the internet has given us access to the stacks of a library so huge that we are all exposed to surprising, intriguing, "pointless" information daily.