As we start to spread the word about Generosity Day 2012 (thanks to all who signed up to be part of the core group  – more coming soon!!), we’ve naturally gotten a lot of “why” questions – mostly from enthusiasts who want to be able to explain the day to others, and some from (friendly) skeptics.

If anything came from the heart for me, it is Generosity Day, so unpacking “why” has been an instructive exercise in reverse engineering of an intuitive decision.  Therefore, this (and subsequent) reflections aren’t answering the question “why did I do it in the first place?” (meaning: this was the plan all along), they’re answering, “what insights have I gained along the way?”

One of the core insights is that for many of us – especially those who are more cerebral (and in this I include a big swath of the “smart philanthropy” crowd, whether donors or social enterprise enthusiasts) – our thinking around smart social change is crowding out our natural instincts about how we want to be in the world.  Put another way, we are letting our thinking about what’s best get in the way of how we want to act.

Ironically, in our pursuit of better solutions, we continually reinforce our own practice of turning things down – things that don’t meet our “evolved” criteria of good social work.  The end result of this is atrophy of our generosity muscle, since anything that is underused withers away in time.

The intentional practice of generosity is a way to strengthen this muscle, to get us more comfortable using it, and to make using it a more regular part of our lives.

That’s very different from claiming that saying “yes” to everything is the best kind of philanthropy.  It isn’t.  But philanthropy that doesn’t incorporate generosity doesn’t make sense in my book.

If you’re the equivalent of muscle-bound when it comes to generosity – if it’s part of who you are and how you walk through the world every day – then you probably don’t need Generosity Day.  But I suspect many of us could use a generosity tune-up.  Indeed, my wager is that a large group of people taking the same leap of faith around generosity, pushing themselves to do something outside of their comfort zone, and then coming back together to share and reflect on that experience, will generate new insights for all of us.

For those in our core group (could be you!) who want to help spread the word about Generosity Day, we’re going to propose undertaking a one week generosity experiment, before October 31st, to see how it feels.

You could give it a go too.

Go ahead, flex the generosity muscle, reflect on the experience, see how it affects how you go through the world.