A few weeks ago I started a generosity experiment.  The idea, sparked by a homeless man to whom I did not give, was to spend a period of time saying ‘yes’ to all requests to give – whether a person on the street, a donation request from a nonprofit, whatever.

Some people, like Jeff, really hated the idea at first (“AHH! NOO! STOP!” was his initial reaction); others shared my sense that the practice of being generous itself was inherently valuable.

A month later, I’m glad for the experiment.  I gave more than I normally do and I gave more often.  And it felt good and right, especially during the holidays, a time when presents of all sorts were flying in all directions.

And while I won’t continue giving to virtually everyone who asks, I will give more and more often.  The practice of being generous instead of critical (discerning?) is, I have found, important for at least two reasons:  first, we are how we act, so if I can habitually act more generous, I will be and become a more generous person.  Second, the experiment served as a deeper exploration of how much giving is an act of self-expression, rather than (or in addition to) a “purchase” of a social outcome.

The people who didn’t like my experiment all said something like, “If I pass a person on the street asking for money, I don’t give because I know it makes more sense to give to a homeless shelter.”  Put another way, one could better purchase social change for a homeless person by giving to a shelter or a food bank.   Objectively, that’s probably true (though one doesn’t know for sure).  However, it also misses something: first, because whether or not you give a dollar or two to a person on the street really doesn’t affect the larger donation you’ll hopefully make to the homeless shelter or the food bank; second, because the act of saying ‘no’ over and over again is reinforcing something in you and in me.

I’m not saying give every time, I’m asking us to be honest about why we do and don’t give, and to recognize the effect it has on us.

Let’s take an extreme example: suppose that over the course of the year I’m asked to give 200 times – maybe 100 times directly and 100 times by various nonprofits in various ways.  And let’s say I have a limited amount of money to give, which I do.  Isn’t the practice of saying ‘no’ 195 times and ‘yes’ 5 times reinforcing a mindset and habit that I’m the kind of person who says no when people ask for help?  And couldn’t there be a way to say “yes” 15 or 50 or 100 times that would reinforce something else entirely?

I don’t want to take this too far – to the conclusion that all philanthropists should spread their funding widely so that they can practice saying ‘yes.’  That’s not right either.

But I do want to push myself and others to ask whether it is healthy to think of every giving decision from the head rather than from the heart.  Can’t the argument that “this isn’t the best use of my money” be paralyzing or, worse, an excuse never to part with any money, because nothing is ever good enough?

Maybe a request for a gift isn’t always chance to analyze what is or isn’t the “best” use of my money.  Instead, maybe a request for a gift is an opportunity to practice being the person that I want to be – someone whose first response is to be open and generous.

And maybe, with practice, I will be transformed in a way that is powerful for me and for the world.

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