I drive by at least a few panhandlers per day. I have never imagined to be one myself. However, Karen from North Carolina wrote me an email describing how tough it is for her to ask for money, even for someone else or for charity. To experience this myself, for hopefully the only time in my life, I took a sign to the street and asked for money for Austin Food Bank. The entrepreneur in me prompted me to test out different signs to gauge their effects.
When you don't normally ask for money, doing so in a public setting can be excruciatingly difficult, as I found out. Among all the panhandlers, those who are honest and are in real need of money for their families, my heart goes out to them. It hurts pride to do this.
Learning: 1. Messaging matters a ton in any requests, whether it's asking customers to buy your product, or asking strangers to give you money for charity. Make sure your message is specific enough that people know where their money is going. 2. Be very careful in using humor. If the humor is not well-designed (like in my case) or in the wrong environment (charity), it could backfire big time.