Dennis Litky, co-founder of Big Picture Learning, and a charismatic and inspired educator, has found that the single most important factor in kids learning is “whether they believe that they can.” That kind of influence from a gifted teacher to a student is profound. We can and do measure the academic progress of the student, but it is harder to quantify the impact of a gifted teacher’s impact on the student. Sometimes though, it is not hard to see:

A TPI colleague has worked for ten years with a client who supports a wide range of small, grassroots organizations. This client also supports many, many, talented and deserving young people with a unique scholarship and mentoring program that has a surprise ending the students are not aware of. He always meets with these kids personally and listens to their stories. I asked my colleague to describe what goes on between the donor and the student. Her answer was this: “Compassion is certainly part of it, but as I watch him with the kids, I think it goes beyond that. If I had to boil it down, I would say it is admiration he feels for their “scrappiness” and desire to make something good out of their lives. Maybe he feels connected to them because he sees in them the qualities that he hopes he has himself demonstrated in life, and those he admires most in other people … hard work, determination, passion. Pride is also part of it … he always tells the students how proud he is to know them, and it is so incredibly genuine and sincere each time he says it.”

So here is this guy sitting there, beaming, and here are these kids rising to his hope and high expectations for them—it is exactly the kind of philanthropy we all want to see. These exchanges are the essence of what Martin Buber called dialogue: the narrow ridge, the place where we meet another. This is the “I and Thou” relationship, where the image of the self is incomplete without the image of the other.  When empathy is established at this highest level, a gift relationship is transformed from one of power and dependency to one of open-hearted mutuality. These are very powerful influences.

In his books on the anatomy of influence, literary critic Harold Bloom describes the poet within the poet—in the greatest of poems is the poetry itself and not something else—it is that moment in the making of poetry, or in the living of life, when a wholeness has emerged, something so authentic that it has become an influence unto itself.

He writes: “But strong critics and strong readers know we cannot understand great literature if we deny literary love to the writers or readers. Sublime literature demands an emotional not an economic investment.”

My take off from Bloom’s insight is remarkably specific to all the Dennis Litkys out there and all the donors who practice the art of philanthropy. There is a gift within the gift—the greatest of gifts is when it transcends the evidence upon which it is based. Its mystery is in the relationships between donor, recipient, and the community of interest that is served. It is a dynamic that operates on multiple levels.

One level is contractual and may be spelled out in considerable detail—for example, a multi-year grant to a youth organization based on research, data, and measurable evidence. Call this level science. But it is the relationships between the parties who have an interest that makes or breaks the success of a program. These relationships flow between the organization’s staff, the youth involved in the program, parents and extended families, and powerful peer-groups, all of which intersect within a community culture. These are the “influences” of a pretty complex system that is part cognitive, part non-cognitive; and therein lies the “love” factor. Therein lies the art.

I agree with Bloom, and I agree with our client—you cannot have a great gift if you deny the donor or the recipient philanthropic love. Sublime philanthropy demands an emotional investment as much as it demands economic and process investment.