When Les Brown started talking to squirrels (especially the one named Tyrone), hootin' and hollerin' with his infectious laugh, I knew that he traversed the path of crazy wisdom. It's a powerful path!
Wiki describes crazy wisdom as "a manifestation of enlightened behavior by persons who have transcended societal norms."
Few are inclined to pursue the path of crazy wisdom, but if you've got these tendencies naturally, then it might be a good idea to start by reading the book Crazy Wisdom by Chögyam Trungpa. I haven't seen the film personally, but it must be interesting and it's now on the list.
coined the term, but crazy wisdom can be found in multiple spiritual traditions. So you don't need to have an affection for Tibetan Buddhism to appreciate crazy wisdom or implement it in your personal or professional affairs.
"Some things are taught, some things are caught."
Crazy wisdom can't be taught, necessarily, but it can be exhibited and therefore modeled. If you find yourself drawn to leaders who step out of line, let them teach you how you can cultivate the courage to be crazy.