Q&A by Jeffrey A. Walker, Ph.D. and Andy McMahon

Where do philosophy and philanthropy intersect? Jeff Walker and Andy McMahon share a love of the two subjects. Here, they talk about a few of their favorite philosophers, ways the subject has helped sharpen their skills, practical applications for prospect development and more.  

McMahon is the assistant director of operations and prospect development at the United States Holocaust Memorial Museum (USHMM), in Washington, D.C. He completed a bachelor of arts in philosophy at Carleton College in 2009. Walker is the director of research in University Advancement at the University of Wisconsin-Milwaukee. He earned a bachelor of arts in philosophy (cum laude and Phi Beta Kappa) at Lawrence University in 1986.

Disclaimer: Andy was interviewed in his personal capacity. The opinions expressed here are his own and do not reflect the view of USHMM or the U.S. government.

Jeff Walker (JW): Why philosophy? Have you always been a very curious, questioning person?

Andy McMahon (AM): I wanted to major in philosophy long before college. No one was pushing me toward Plato or Kant. I was actually inspired by the first “Matrix” movie. What if we are all brains in a vat? What if reality is a simulation? I explored these and other possibilities with my high school philosophy club and kept wanting more. I even bought a copy of “Tractatus Logico-Philosophicus” — though I barely comprehended a word.

College philosophy often left me confused as well. I didn’t feel I could understand the reading and complete the major until I took a logic class. It helped me become a better writer and transformed me as a thinker, though its potential to help us avoid errors is often exaggerated, on the internet and elsewhere.

JW: How funny that we had the same textbook, “Symbolic Logic,” by Irving M. Copi. A classic.

AM: Yes, but there wasn’t much hilarity at the time. Remember the endless truth tables? Ugh!

I’m wondering: Did you find that philosophy mainly helped sharpen your critical thinking skills? Were there other practical effects?

JW: For me, philosophy involved new habits of thinking, reading and writing — all tightly intertwined. One initially intimidating professor (but eventually a lifelong mentor) promoted the most self-disciplined writing I had ever experienced: unwaveringly clear and concise, absolutely no exceptions. When he gave an essay-writing assignment and asked for “750 well-chosen words,” that’s precisely what he meant. Unless you were turning in A-plus prose, going over the word limit resulted in a significantly lower grade. It was a tough, enduring, valuable lesson.

That brings me around to the practical impact of studying philosophy. If you take it seriously, as you and I did, you become habitually more careful about language — both what you observe and what you produce. That primes you for success in many professional contexts.

I’d love to hear more about the intellectual doors your logic course opened. Did it ultimately lead you to a favorite branch, school or period of philosophy?

AM: Originally, I found skepticism thrilling.

JW: David Hume, perhaps? I remember his unsettling argument that we can’t know for sure the sun will come up tomorrow, solely because it always has in the past.

AM: Yes, Hume — among others. As I neared graduation, I decided external world skepticism was a parlor game that had gone too far. Fortunately, around the same time, a favorite professor introduced me to the work of philosopher John McDowell. Inspired by the later Wittgenstein, McDowell believes that many philosophical problems — external world skepticism being one — look impossible to solve because of their framing.

But McDowell also says, persuasively, that we can’t really answer convinced external world skeptics on their own terms. Instead, we need to expose their problematic assumptions and then find viable alternatives — which is often easier said than done. McDowell thinks doing philosophy should be liberating. To borrow a famous image from Wittgenstein, it can be like freeing a fly, hopelessly stuck in a bottle.

Many people find this way of doing philosophy unsatisfying, because you aren’t building grand explanatory theories. Although I agree with McDowell’s approach, I’ll confess that I keep reading sticky philosophy and see value in it. I'm like that fly, constantly finding my way into new bottles.

What about you? Are there philosophers you still think about?

JW: The ancient Greeks intrigued me, but I really got excited about the American pragmatists: Charles Sanders Peirce, William James, John Dewey and Richard Rorty. I was fascinated by their claim that truth isn’t some frozen abstraction but, rather, a matter of evolving consensus: a guide for action, a tool, that helps us solve genuine problems in our everyday lives. Although I loved logic just as passionately as I had loved high school geometry — and while I found doing the truth tables you mentioned strangely relaxing — I wanted “truth” to be something more. I found that in pragmatism. Truth is what works: an intelligently stated principle that serves the greater good.

Rorty’s street-level definition of “conservatives” and “liberals” was another revelation. He said the former are the most afraid of societal disruption and the latter, of causing pain for other people. That simple yet eye-opening reframing can lower the temperature in charged political conversations, at least a bit.

I’d like us to dig into this notion of philosophical concepts and questions as practical tools. As you reflect on your career and your accomplishments at USHMM, what aspects of philosophy have been the most valuable in your professional toolbox, and why?

AM: Despite what many on the internet seem to think, deductive logic is not a silver bullet. It’s never possible to make all of our assumptions and inferences explicit, or to avoid all errors by memorizing a list of fallacies. But logic can help anyone in prospect development (PD) draw better inferences and avoid some unwarranted conclusions. Knowing that our colleagues will act on the information and analysis we provide, we have an obligation to be as careful as possible. Logic helps me slow down and reason more intentionally.

Perhaps surprisingly, I also find insights from the philosophy of science useful in PD. For example, there are always multiple ways to explain the same data. Even a comprehensive theory that accounts for every fact isn’t necessarily correct. This applies not just to the results of scientific experiments, but also to our constituent data and donor portfolios. Philosophy keeps you humble. It makes you pause and reminds you not to shackle yourself to a single set of ideas or one explanation.

JW: To many Apra members, as well as many non-PD philanthropy professionals, a background in philosophy might seem both unusual and unsuitable. How would you respond?

AM: Philanthropy is about getting good things done, not just having interesting intellectual discussions. An ongoing challenge for our field is to clarify what we mean by terms like capacity, qualification, inclination and affinity. These aren’t self-interpreting, though sometimes we talk as if they are. We must think systematically about how they relate to each other and find ways to interpret and measure each for our own unique constituencies. We also need to clarify our assumptions, explore the consequences of our definitions, and make revisions when necessary.

That’s exactly what philosophy teaches us to do, and the “we” here is crucial. You can’t expect to make much progress by thinking alone in a room. Despite their reputation for navel-gazing, philosophers teach us that, when we reason together as a community, we just might make progress. We can make our ideas clearer and more useful than they were before.

JW: Andy, I’ve enjoyed our conversation so much. Thank you!

AM: Thank you, too!