If a person works for their life to pursue their passions it is a self awareness. I respect that. I think most people do. He isn't selling his soul. He just asks questions and is stupid about most stuff. He is a comedian. Has he said shocking things? Sure. Eminem has. Howard Stern has. Elvis has. So many artists have done what they needed to do to pursue their passions. And if that makes him deplorable, sure.
My point is that he earned his money to chase his passions and their is nothing wrong with having the freedom to do so. And planning for that for your own fulfillment is admirable. It is intelligent to be aware of yourself and your surroundings to work to achieve that.