Years ago in a conversation with the editor of a now defunct magazine focused on philanthropy, I asked how ideas for stories were developed. The answer I got was at once funny and chilling: “We have this tall stack of all prior issues of the magazine in the corner of my office, and we just pick a point in the pile, wiggle out an old issue, and then rewrite the main story.” This anecdote stuck with me because in recent years I have come to believe that not much new is possible to say about mainstream American philanthropy. Many of the big issues have been clarified, the pros and cons of different approaches articulated and argued out in many different fora, and the outlines of what constitutes good practice sketched so many times by so many people, including by myself, that I wonder what is really left to say. And of course, there remain many issues in philanthropy that are simply unresolvable and unknowable, now and in the future.

In his new article on effective grantmaking, Paul Brest dutifully tries to set out the major critiques of the broadest of all concepts, namely the notion of strategic philanthropy. While Brest starts with a well-defined target and then shows us what arrows have been aimed at it, the piece is entirely barren of any evidence that would decide the issue of whether strategy, planning, and assessment make philanthropy more or less effective. And to his credit, Brest forthrightly admits this: “It would be difficult to design an experiment to answer the question empirically—especially—but not only, because of the tremendous variety and inherent subjectivity of philanthropic goals.”

Brest goes on to note that the case for strategic philanthropy ultimately rests on a hunch, or “belief,” that “the intentional, systematic, and rational pursuit of an outcome increases the chances of achieving it.” Who could argue with that? One might well ask. But the question that follows is more troubling: What are we really talking about when we discuss strategic philanthropy and whether it might be an effective approach to grantmaking? The answer is that we are talking about something as ambiguous as whether the world is really governed by rational technical considerations or whether it is fundamentally unpredictable and erratic. Talk about a philosophical dead end.

The debate about strategic philanthropy thus turns out to be a metaphor for a larger debate about how society works and how social change is achieved. It is the same debate we might have about government policies and public programs. Can we improve the results of our policy making with prior analysis and careful goal setting? History has shown that the answer is maybe, but then again maybe not. We can cite evidence and anecdotes on both sides of the proposition, cases where forethought and planning proved useful and other cases where the huddles of implementation swamped everything that came before it. The same is likely the case for philanthropy. Strategic philanthropy has worked in some cases to secure useful results. In other cases, it has been a dismal failure.

In the end, Brest’s article convinces the reader that planning and strategy are probably good things and that all the criticism mounted against them does not overcome the likely benefits of trying to clarify intent before giving and then following it up with sound grantmaking practices. Brest is on to something here. In fact, one of the least appreciated aspects of strategic philanthropy lies in the process that it entails, not necessarily in the results that it produces.

The very act of trying to be strategic—regardless of whether successful or not—is probably beneficial if for no other reason than that it forces greater reflection and real discussions of about underlying intentions, assumptions, and biases. The strategy finally settled upon might go right out the window as soon as reality on the ground is confronted, but no matter. The very act of strategizing prepares the grantmaker for the chaos that often lies ahead in the fog of war that is philanthropy. Thus, as US President Dwight D. Eisenhower famously noted, we might conclude about philanthropy: “Plans are worthless. Planning is everything.”

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