In our 2020 article, The Case for Self Reflection, Paul Brest, Erinn Andrews, and I described philanthropy as a journey, one marked by both anticipated and unexpected experiences and countless opportunities for learning. We argued that periodic reflection helps us stay connected to why we embarked on that journey in the first place and enables us to adjust our course as conditions change.
A lot has changed since then. Several of my projects have since come to fruition; I spent down and closed my family foundation; and I have stepped back to spend more time with my family. During the same time, the field of philanthropy has also changed. The economic situation facing many of our partners has become more fraught, and there is a movement within the field to provide our partners with greater operational and strategic flexibility.
With this in mind, I might change the questions for reflection as follows:
Externalities— How are external forces impacting my partners and their ability to meet their stated goals?
Movement of capital— Am I moving dollars to my partners in a meaningful manner? Is my grant strategy meeting the moment? Do I need to change direction? Should I consider increasing the size of my annual budget? Are there strategies to better support my partners, such as making multi-year commitments, increasing the grant size, or accelerating an annual grant?
Impact and progress— What was the long-term impact of my grants both at the individual and portfolio level? How did my grants support or facilitate my partners' abilities to meet their strategic goals and objectives? At both the individual and portfolio level, was there meaningful progress during the grant period?
The value of good leadership— Did I give to the right leaders? Are they in touch with their communities? Do they understand the challenges and key levers of change? Can they advocate on behalf of their community? How good are they at execution?
Should I continue the journey and renew the grant?— Where am I on my personal philanthropy journey? Is this still an area of focus? Do I feel connected to this cause and/or organization? Did this specific organization deliver? How stable is this organization? Do I have a solid working relationship with the leaders and people in this organization? Is this a natural time to change direction or transition out? (leadership transitions, spending down, retirement, strategic refresh)
Looking back, my philanthropic career has been personally rewarding. I am struck by how much my partner organizations have achieved and how many lives I have had the opportunity to positively impact. That said, every so often, it has been good to look over my shoulder and reflect. You never know if you could do better unless you check in and ask the hard questions.
