Given the human mind's strong preference for certainty, why would we engage in the intentional cultivation of doubt?
Well . . . how's certainty working out for you? Probably not so well.
The universe is in constant flux, which explains why we crave certainty . . . and also explains why we never get it.
Consequently Buddhism emphasizes great doubt as a way to align life with reality.
Artists work with doubt to create an opening where something new might appear. Zen teachers do the same with kong-ans (koans).
For the most part, modern culture barely tolerates doubt. That's why I was delighted to come across this short, enigmatic (zennish?) video on the topic. I hope you enjoy it!