In commenting on Paul Brest’s thoughtful and dense article, it is best to start with his conclusion, where he writes: “The case for strategic philanthropy ultimately is based on the belief that the intentional, systematic, and rational pursuit of an outcome increases the chances of achieving it.” Underscoring this conviction is his use of terms like “flight plan” and related imagery for describing the sequence of decisions and actions towards intended goals or results.

At first, these descriptions seem like rather modest claims, and one wonders if other forms of philanthropy, even charity, would rest on fundamentally different grounds. But underneath the modesty of Brest’s claim is a strong belief in rationality, of the mastery of the world, to evoke a Weberian image, and the conviction that some form of orderly change is possible if planned and executed well.

Brest, however, goes even deeper, contrasting his insights with the Burkian fear that society, with its overwhelmingly complex tapestry of networks, institutions, and organizations, and its deeply embedded values and inert practices, lies “beyond the grasp of policy makers, and that heroic efforts to improve matters can have disastrous unanticipated consequences.” For the strategic philanthropist, action is better than no action; and any flight plan—however insufficient for navigating the complex and messy patterns of ever changing modern societies—is better than no plan at all. Strategic philanthropists can identify and grasp concrete facets of social causality, i.e., a ‘theory of change,’ and they can use them to achieve the desired outcomes. This seems to be the premise that informs much of Brest’s article.

We would like to offer a different interpretation of strategic philanthropy, one that puts the belief in rationality in context, including its comparative advantage over other ways of philanthropic conduct such as charity or passion for a particular cause. Our view is based in part on Albert Hirschman’s “Principle of the Hiding Hand.”¹ To appreciate the importance of his principle, we should recall that strategic philanthropy, simply put, is a set of decisions and actions intended to achieve some desired outcomes under conditions of uncertainty and through ways and means that are beyond quick fixes and that require some level of flexibility, innovativeness, even creativity. If that were not the case, we would not have to be strategic in the first place and could apply standard operating procedures.

Hirschman observed various projects that from hindsight looked unrealistic, over-ambitious, dilettante, or even deceitful. Examples include many of the infrastructure projects in 19th century America, development efforts in 1960s Africa, public housing in the 1970s, nuclear waste management in the 1980s, developing civil society in Eastern Europe in the 1990s, democratization of Middle Eastern countries in the 2000s, and sustainable agriculture today.

Hirschman argues that if the project planners had known in advance all the difficulties and troubles that were lying in wait for them, they probably would never have begun. But they did. Which raises the question: Why do some people—especially entrepreneurs, planners, politicians, and, yes, philanthropists—take on tasks that seem near impossible, that carry high risks and huge costs of failure? That is where the principle of the hiding hand comes in. Hirschman writes:

This is the flight plan Brest speaks about: We can change the American political system, and we have a plan. We can mitigate the adverse effects of climate change, and we have a plan. We can change the world for the better, and we have a plan. By necessarily underestimating our creativity or resourcefulness ex ante, we may well underestimate to a roughly similar extent the difficulties of the task itself. In a way, writes Hirschman, we trick ourselves “by these two offsetting underestimates into undertaking tasks which we can, but otherwise would not dare, tackle.”

For us, this is the key to strategic philanthropy, or creative philanthropy as we have called it:² it kicks off a process towards some desired goal without fully knowing how to achieve it, nor knowing all the consequences of intermediary steps, or even the consequences of achieving the actual outcomes. We may know some aspects of what is involved, be more certain about some facets than others, and even believe in the flight plans and metrics put forth, but fundamentally we are engaging in a similar double underestimation.

In other words, strategic philanthropy means letting ourselves be tricked by two offsetting underestimations: first, that it can be done within our means and in known ways, and, second, that it is not that difficult after all, and that all can be achieved if only we are good at what we do. The independence of foundations from market considerations and the ballot box gives them immense freedom to let themselves be tricked. No dominant stakeholder keeps foundation ambitions in check. This is the source of their true resourcefulness and innovative potential.

Could it be that some or perhaps many of the proud achievements of philanthropy were of this kind:³ taking on seemingly impossible tasks but believing they are achievable because we have what it takes? Would the Rockefeller Foundation have founded universities otherwise? Would the Green Plan have found its way to Africa, or would the Ford Foundation and others have funded the Civil Rights Movement? Would the various and often youthful strategic philanthropists in the San Francisco Bay Area today go about their projects if they really knew what was involved? Hirschman would argue that the hiding hand protects latter-day venture philanthropists as it did the Rockefellers and Fords in times past.

Strategic philanthropy involves uncertainty. The emphasis on metrics may ultimately serve more as some form of psychological insurance under the hiding hand principle than a truly needed measure of performance or goal attainment. As measurability approaches plan-ability, the strategic becomes less important. Strategic planning acts as both encouragement (to attempt the task) and reassurance—if nothing else, a strategy assures the board, donor, and other stakeholders that things are under control: ‘we know what we are doing,’ ‘this is considered and professional.’

Indeed, for the principle of the hiding hand to work, strategic philanthropy requires conditions that foster creativity and innovation, and a willingness to let ourselves being tricked. In practice, strategic philanthropy is less of a flight plan and more of an open floor architecture in which one can re-invent the wheel at least once if need be. It requires a culture of accepting failure, and of rewarding trying as much as success itself. Above all, strategic philanthropy requires the realization that passion for a cause is as important as its rational pursuit.

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