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On Monday, May 11th we raised a glass in honor of TPI’s 25th birthday. Many, many thanks to all the friends who joined us for the day and to the many more who sent their regards from afar. It was a great party. We celebrated with applause and toasts and, of course, thought provoking conversations about looking back and looking ahead. And though the celebration is over, the pleasure of seeing friends, colleagues and clients a memory to savor, we return to the work we love to do, refreshed, inspired and challenged.

The theme of the day was “Bold Questions” for philanthropy and the air was electric with them. Subsequent posts will focus on a few of those questions in greater depth, but for now, to whet your appetite, here is a sampling:

  • Melinda Marble, of Pilot House Associates, wondered aloud to the crowd: Are my gifts doing harm? What are the unforeseen consequences of our good intentions? (And told a great story to illustrate.)
  • Peter Karoff, TPI’s founder asked: In our quest for measurement, have we lost the “love” aspect of philanthropy? (And cited wonderful poetry that inspired.)
  • Peter Buffett, musician and Co-President of the NoVo Foundation asked: Are funders creating the conditions for deep listening and bottom up, sustainable change? (And treated our ears to his magnificent music.)
  • Paul Grogan, President of the Boston Foundation, challenged us all to think: Are we truly working at the systemic level of change? (And reminded us all about what’s possible.)

Act boldy. Give wisely. This is TPI’s tagline, and at the ripe age of 25 we suggest that to act boldly we must ask bold questions – of ourselves, of others, of the field of philanthropy as a whole. Bold questions expose assumptions, overcome inertia, stimulate innovation. They foster discussion and require action; in fact, asking them is one of the most important responsibilities of philanthropy.

Stay tuned for more on the 25th in the weeks to come. In the meantime, we challenge you to ponder what your own bold questions may be as you look ahead to the days, months, years to come. Care to share?