I went out to lunch with a business associate today. She wanted to pay for our meal. I was fine with that. She needed a single to tip the valet and asked if she could borrow it from me. I was fine with that too. Then she was absolutely insistent that she pay me back the $1 she borrowed. I don’t think I’m fine with that.

She had the best intentions. She hates to borrow. She likes to be generous. The last thing she wants is for anyone to feel that she is taking from them. But she missed something very important. I don’t care about the dollar, but I do care about being generous.

I like to be generous with other people. It makes me feel good. When she insisted on paying back the dollar it made me feel cheap. It took away from me the joy of doing something nice for her. So she wouldn’t take the dollar from me, something I didn’t care about, but she would take the pleasure of generosity from me, something that means a great deal.

This is a common theme in my coaching as well. My clients don’t talk about borrowing $1. However, they often tell me about situations in which they acted with the best intentions. Unknowingly, their actions actually had the opposite impact of what they intended. One reason this happens is that they fail to imagine what the other person wants. My colleague assumed that I wanted my dollar and focused on her own desire to not feel cheap. She failed to think of any alternative desires I might have. She didn’t think I might want to be generous. Or that I might want our relationship to feel more like a friendship in which case neither of us would think twice about $1.

So if you are going to be generous, give freely. Just remember, try to give something that people want. And if they so desire, let them be generous in return.