Ask for feedback from people with diverse backgrounds. Each one will tell you one useful thing. If you're at the top of the chain, sometimes people won't give you honest feedback because they're afraid. In this case, disguise yourself, or get feedback from other sources.
If you don't have a passion, you'll give up.
Because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well worn path.
In order to learn how to do something well, you have to fail sometimes. In order to fail, there has to be a measurement system. And that's the problem with most philanthropy - there's no measurement system. You give somebody some money to do something and most of the time you can really never measure whether you failed or succeeded in your judgment of that person or his ideas or their implementation.