This is a super lovely post honestly! I have not yet conquored the speed woobles, but I have said fuck it for looking cool! The only way to really do something well is to let loose and be one with what your doing, and not let fear of others or fear of injury stop you! It goes for dancing or skating I guess.
Personally I longboard around town, I love going fast and feeling the air in my hair, and its a pretty cheap and effective mode of transportation!