This is a completely spontaneous request of my readers to give me feedback on a delicate issue.

When I was homeless, I spoke the words “can you spare some change?” exactly once. From the reaction of the two men walking past me, I told myself instantly I would never put myself through that awful combination of guilt, shame, embarrassment, and anger again.

From that moment on, I either busked or sat silently flying a sign which read:

BROKE AND HOMELESS
OFTEN HUNGRY
PLEASE HELP IF YOU CAN

If I had it together well enough to busk (e.g., had a musical instrument I could keep from getting stolen or from the fear thereof), I would sometimes make up to $100, and on one unusual occasion got $100 for a single song (that I was singing while playing drums on my pants legs). The guy who gave me the $100 (a Ben Franklin) later turned out to be a street dealer suspecting me of being a “meth-head” and looking for a customer.

I never talked to him again and in fact $60 was stolen from me later that evening. (I didn’t like to keep cash on me because it would get around, and one of the local alcoholics had witnessed the deal from nearby.)

I don’t think anyone particularly likes to ask for money in any context. I feel weird about even having a donate button sometimes. But there is a parallel between “flying a sign” and a “donate button.” In each case, I am not verbally requesting money. I am only presenting the fact that I would like some.

I know some fairly well-off people in town here, who will testify to the truth that I have never asked any of them for money for personal needs, although they have seen the “donate” button on my blogs and newsletters.

What are your feelings about asking for money? On the one hand, I don’t like to go through that awful sensation. On the other hand, I sometimes think that — given my circumstances — I am just too afraid to ask.

I also do ask God sometimes for money, and sometimes later on somebody gives me some money, sometimes even the exact figure I asked for. This leads me to believe that God probably wants me to ask Him first, no matter what choice I make later. But those events are far and few between. God doesn’t just dish out the dough like a sugar daddy.

Matthew 6:33