On Saturday evening in Denver, I had the great pleasure of hearing one of the best talks on philanthropy I have ever heard.  The venue was the Association of Black Foundation Executives’ James A. Joseph Lecture and the speaker was Crystal Hayling, a member of CEP’s board.  Crystal, who was until December the president of the Blue Shield of California Foundation, and is now living in Singapore with her family, entitled her talk 5 Things We Know, But Keep Forgetting.

Describing the first of the “5 Things,” she said:

Number 1: We should take more risk.

I don’t mean the kind of risk that is a narrow calculation of whether this grantee has a 48 or 63% chance of achieving these four goals. When we define risk in philanthropy we place it outside of our own walls and begin to assess the grantees’ risk of success or failure. But I am talking about us taking more risk. And I mean heart-stopping, “omigosh what have we just done?” “is that even legal?” kind of risk. The kind of risk that makes the safety players chuckle uncomfortably and snidely remark, “Gee, I hope that works out for them.”

Nehru once said, “The policy of being too cautious is the greatest risk of all.” But that is not how it feels when making grantmaking decisions.

When I think about risk, I think about the people I know who have taken big risks. My dad for one. He was raised in a Southern Black upper class, lower-income family. You know. We have those in our community. Black folks who had risen in “class” because of their education if not because of the size of their wallets.

My dad was the son of those kind of Black folks. And he risked stepping off that precarious rung on the upwardly mobile ladder, to be a civil rights activist. To be in solidarity not with his ability to get ‘up and out’, but in solidarity with his community. And he risked his parents’ disapproval. Something we don’t often talk about is that everyone in our community supports civil rights leaders NOW, but everyone didn’t support them then. Many, like my father, heard constant admonitions to stop “worrying about all that marchin’ foolishness” which was clearly preventing him from grabbing the brass ring that, as a trained dentist, was so within his reach.

So how has that shaped how I think about risk in philanthropy? It reminds me that risk needs to feel personal. It needs to feel dangerous.  I haven’t felt that as often as I would like, but I have felt it. Like when I worked at the California Wellness Foundation almost 20 years ago and we launched a $30 million youth violence prevention initiative. We were a brand new foundation and I remember meeting with some established foundations. You’d have thought we had hillbilly painted on our foreheads. They questioned our science, poked holes in our theory, and seemed to say, “who do you think you are anyway, talking about $30 million?” And then we went into communities where parents of kids who’d been shot in drive-by’s asked us how dare we think some little bit of our money was going to change anything. I remember being mortified, and then I remember thinking about my dad and thinking, “Well we may not be right, but we better go ahead and find out.” There was too much at stake not to try.

I want to take the kind of risk guaranteed to piss someone off.

And not just the detractors. We have to be willing to piss off our friends and allies as well. To avoid the group think. There are examples: the education funders who want to strengthen public education but who supported charter schools, the funders who support and criticize the Gate’s Foundation’s approach to public health. When I took over the Blue Shield of California Foundation, many of my friends thought I had gone over to the dark side because our foundation was staunchly supporting the notion that every American not only has a right to health insurance, but also has a responsibility to have it. The idea of the individual mandate, a part of the recent historic health reform legislation, made us pariahs among the health advocates in California. And this was just 5 years ago. In order for risk to have real consequences, think of it less in terms of will this project succeed or fail, but will this funding have the opportunity to dramatically push progress forward and will it outweigh a real and tangible alternative use of the funds.

To quote the great American philosopher Chris Rock (who is in fact quoting his mother), “She would always say, If they don’t pay your bills and they can’t beat your ass, what do you care what they think of you?”

In order to take risks, we need thicker skins. Number one: Take more risk.

Crystal went on to describe the four other “things we know but keep forgeting.”  Number 2:  The time is now.  Number 3: Design matters. Number 4: Technology is just a tool. But it’s a power tool.  Number 5: We Need New Leadership.

This was the kind of talk that simultaneously inspires you and makes you reach for a notebook and pen.  Crystal’s words got me thinking in a way most talks don’t.

It’s well worth reading every word.