It’s been more than two years since my original Generosity Experiment. The experiment was an intuitive, gut reaction to an incongruence I felt between my commitment to creating massive social change, my work with philanthropists to support this mission, and how I saw myself behave in the face of acute need right in front of me. The “Experiment” was just that: a chance to test what it felt like to live with a totally different orientation. It was a commitment to take a door that was too closed for my taste and open it wide.
Of course the story spread thanks to Generosity Day last year and my Generosity Experiment talk getting posted on TED, so I’m having (and witnessing) a lot more conversations about generosity and Generosity Day.
One thing I’ve observed is that the powerful original story – of giving to a homeless person when asked – is both helping and hindering my ability to explain what Generosity Day is all about. To be clear, generosity day is not designed to be a philanthropic strategy (“say yes to everything”). Rather, the whole point is to use the day (the month) to develop a different practice of generosity in our lives – whatever that means to you.
Since I’m a visual thinker, I’ve drawn some graphs to explain what the Generosity Experiment meant in my life. The red line represents my perceived “ideal” level of generosity (for me). The blue line represents my perception of how generous I actually am.

In the time leading up to my original Generosity Experiment, two things were happening. First, because I was spending so much time with philanthropists, I was gaining a deeper understanding of philanthropy and of giving, and part of my reflection was that generosity was more important than I’d understood it to be. That’s why the red line slopes upwards: what I understood to be the “ideal” in terms of generosity was going up.
Second, you’ll notice that the blue line (my perception of how generous I actually am), is sloping down. That reflects my experience of spending all my time and energy understanding how difficult it is to create social change efforts that really make a difference. And so, increasingly, I began to feel like more and more things didn’t hit the bar (“what’s the model for sustainability?” “show me your impact numbers!” “what’s your broader theory of change?” etc.), which, practically speaking, meant that I was saying “no” to more and more people/organizations that were asking for my support.
This is what I meant when I said that I felt like what was smart was keeping me from doing what was right.
This next graph represents what happens (could happen) when you conduct a generosity experiment. You choose to be exceptionally generous and open for a period of time. That experience changes you. It gives you the opportunity to reflect on old habits and consider whether they’re still serving you well. Of course the experiment eventually ends, and you revert to “regular life,” but if the experiment changed you in some significant way, then you reset to a “new normal” of generosity (again, whatever that means to you) – in the graph, that’s why the blue line stays above the red line after the Generosity Experiment.

To you psychoanalytically-minded folks out there, a generosity experiment is a tiny undertaking in cognitive behavioral therapy. For those on the more spiritual end of the spectrum, it is like a yoga or a meditation practice – a chance, in a controlled environment for a defined period of time to practice acting differently so that, over time, new practices pervade your life.
Of course the big question is: what happens in just one day? Does it touch peoples’ hearts enough to create a little shift? Are enough people touched by millions of acts of generosity that they’re changed as well? And if we can create a shift for millions of people, will that create a massive change? I think it will.
Outside of revealing what an incredible analytical dork I am, I hope this post can help broaden the conversation – your conversation – about generosity day.
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