I've presented two ways of risking something--being honest about privilege and practicing connected philanthropy.
What are other ways that people with privilege can risk something? The following is a thoroughly incomplete list and I hope readers will comment with other ideas.
RISK BEING FINANCIALLY IMPRUDENT: I should be open to opportunities for my financial privilege to be used in donation-worthy situations that I am directly involved in (as opposed to only using it in situations I'm personally disconnected from). For example, what if your financially-struggling friend is starting up an amazing non-profit and is looking for help? Many people would say don't touch it...I'm suggesting not only jump in, but be transparent about it with your friend. This goes against a lot of "common sense" wealth advice, which advises people never to mix their personal lives and their philanthropy, and DEFINITELY not to reveal one's willingness to contribute resources.
RISKS: I could be judged. Someone could take advantage of me for financial gain. My relationship with my friend could become complicated. BENEFITS: I actually see my privilege doing good for people who are personally important to me. I feel free because I'm no longer hiding this integral part of my identity anymore out of guilt or fear. My friendship has the potential to grow stronger through entering unexplored parts of our friendship together. QUESTIONS I WOULD ASK MYSELF: What would someone taking advantage of someone financially in this situation look like? Am I a good judge of character and intentions? If financial catastrophe were to occur, who would have my back? KARMA: if I give of myself and my resources, does it make it more likely that I won't be left alone to fall if something terrible were to happen to me?