Crystal Hayling, the former president of the Blue Shield of California Foundation was the 2010 Association of Black Foundation Executives James Joseph Lecturer this year and is subsequently my newest Fairy Godmentor. Crystal started her remarks with the idea that foundation staff need to take risks. Not the little risks like letting a grantee turn in a report two weeks late and suddenly feeling like some sort of maverick grantmaker but real risks that are personal and dangerous. If you aren't sometimes ticking off your friends and allies because you have decided to work on an unpopular issue or you have taken a job that people think is too risky you aren't trying hard enough. She said "the policy of being too cautious is the greatest risk of all."
She is also on my fairy godmentor list because she had the nerve to quote Chris Rock's mom at a philanthropy gathering. In regards to people who are asking you to play it safe, Chris Rock's mom said "if they aren't paying your bills and they can't kick your ass, why do you care what they think?"
In philanthropy we are often too afraid to accept the risks that come with not playing it safe, but that is where the best in all of us comes out.