Philanthropists are in the enviable position of determining their own bottom line. On the one hand if you are trying to achieve something, then by definition you may not achieve it and therefore “fail”. On the other hand, if you are giving money away you are only able to fail the people you hope to help. You can’t personally “fail”.
So if you can’t fail why aim low? Why not strive to do the impossible? Why not make mistakes and then try again tomorrow?
One of the reasons that philanthropy is often compared to venture capital, is because venture capitalists make lots of long shot investments with the expectation that most will fail but some will wildly succeed. Of course a VC really can fail because if they have too few wild successes they will run out of money an not be able to make any more investments. Most philanthropists don’t plan on their philanthropic investments achieving any financial return and so they are not dependent on “successful” grantmaking to make more grants in the future.
In the end, I think the biggest risk to a philanthropist is the risk of playing things too safely. The fallout of playing things too safely is that you end up with a long list of nice things you’ve done for other people, but nothing really to show for it.
Since you know you can’t fail, what are you going to do?