We’ve all been in a position where someone has asked us for money … or been the one asking for money. Whether the “ask” be for a donation to charity, or a request for a loan, or an investment in a new business venture, we’ve all been asked for money.

And when you have money, it seems you get asked for it … a lot.

I’ve found it to be an uncomfortable position … whether you’re the person doing the asking, or the person being asked.

So, how do you make it more comfortable?

Personally, I think it’s all about empowerment … for both you and the asker. When someone asks you for money, it is a chance to empower yourself and them. When I stand firmly in my core values and purpose, I am able to hear the request more objectively. I can hear what’s behind the words. And, there may be some answers I’d like to hear. For example:

From the perspective of how will it empower the one doing the asking: Why are they asking for this? What’s really behind this request? Will this gift/investment enhance their life? Will it enable them to make a significant difference in other’s lives, as well as their own? How much do I trust them to use the gift/investment wisely? What do I know about this person’s ability and capacity to make dreams come true? How will they do it? How will it transform and add meaning to this person’s (or others) life?

From the perspective of how it will empower me: What do I really want to know? What impact will it have on me … both emotionally and financially? Can I afford this? Can I afford not to do this? What do I want to learn from this gift/investment? Is this a dream/journey on which I want to join this person? What role … other than the gift of money … do I want to play in helping this dream come true? What other treasures (non­financial) do I have to contribute to the making of this dream? Will I have fun and enjoy this investment? What type of meaning will it add to my life?

Rarely is it a simple “yes” or “no” answer

A wonderful opportunity opens up for us when someone pops the question. Use it as a learning opportunity! If you make decisions by yourself, as a young couple, as a parent, or as a family, make the time to practice … to learn … how to answer these types of questions. And don’t be afraid to ask the big questions.

By practicing, we learn what is important to each other. And if you listen carefully, you’ll gain a little more insight into who you are, your children are, your spouse is, and who your grown­up family has become.