Teaching Relational Generosity

Sarah B. Drummond
6 min readMay 17, 2024

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At UMass Dartmouth’s graduation ceremony yesterday, telecommunications entrepreneur Rob Hale announced during his commencement address that he would give all 3,000 graduates gifts of $1,000. Hale challenged them to use $500 for whatever they wanted, and to give the other $500 to a person or organization in need. The gesture was lovely, and Hale teared up when receiving students’ cheers.

It would be easy to come up with cynical takes on this commencement speaker’s generous surprise. “Hale did the same thing at UMass Boston last year; how can we get him to speak here next year?” “$100K in educational debt, but look at that graduation present!” “Don’t tell Congress about Hale, because they might claim graduation speakers mean we don’t need higher education lending reform.” But I choose to focus on the positive: Hale’s goal, which I believe was to teach graduates something about generosity.

The $500/$500 split gift implies that graduates will understand generosity better if they both give and receive it. Hale’s gift suggests that the joys of giving and of receiving are connected in ways where the meaning of one can only go as deep as the satisfaction of the other. Generosity can take many forms, and all of them are taught and learned. The 50%/50% principle behind Hale’s financial gift has implications for teaching students to be all kinds of generous.

The sort of generosity on my mind today is the kind of generosity we need to be in-community with others. Empathy, like money, is a precious resource. We can extend it to others generously, or we can withhold it. When we give people the benefit of the doubt, and they do the same for us, we find satisfaction and connection with others. How do we teach people to be generous in their extension of grace to others in their communities?

The 50%/50% rule might provide guidance. We grow in our capacity to love, after all, by loving people and allowing ourselves to be loved in return. If you want to have a friend, be a friend. It’s not a matter of quid pro quo, but rather of de-centering our own experiences in favor of a worldview where we know that everyone in a community has experiences, and ours are just ours. Unlike money, empathy for others isn’t a finite resource. The more we extend, the more it comes back to us.

Tomorrow, students at the school I lead, Andover Newton Seminary at Yale Divinity School, will receive their Andover Newton diplomas. All of Yale will have its graduation Monday. I wonder to myself whether we’ve done all we could to teach our students to be generous with others in their communities. The protests on campuses across America have laid bare estrangement between students and their campus leaders, and our graduates will so quickly become communal leaders themselves, I wish I had time to teach them more about being generous with each other.

Watching this class graduate brings up intense emotions for me, as graduating students were first-year students in our three-year program during what I would describe as a particularly difficult time to be a leader, academic year 2021–2022. One might guess that the previous years would have been far worse, one interrupted by a Covid-19 lockdown, and another mostly online. The fall of 2021 was tougher for me, however, in part because it seemed like it should have been one big celebration.

In a season of emergence, we tried to get things back to normal too quickly, when the community-building tools we knew how to use weren’t available to us. For example, Yale’s Covid policies called for everyone to wear masks, which made reading group dynamics difficult. They allowed for gathering for class, but not for friendly discussion outside of class, which is often where the real learning takes place. Policies called for restrictions on worship, including awkward rules that wrung the holiness out of cherished rituals. Worst of all, Covid rules counter-indicated eating together, which felt like a loss at a basic, incarnate level.

Just before Covid, we’d been experiencing some conflict in our community over some incidents that had brought up tension in our unusually racially diverse community. Suddenly, we weren’t together to work through them. During Covid, I felt as though the tide had gone all the way out, exposing a sea bed of ugliness that had been — and still is — always there, under the surface. White supremacy and misogyny, both so connected with powerful people as to appear to be state-sanctioned, stood up and waved, and we couldn’t get together to talk about what it all meant.

When I came out from Covid isolation, I found I had changed. An extreme extrovert by nature, I had learned to enjoy my own company, but I had also been miserable on a deep level. By necessity, I’d placed that misery on-ice, and the pain of coming out of numbness was intense. I would joke that I’d developed late-onset social anxiety, but the truth was that I was scared to be around people again and couldn’t remember how to do it.

In the fall of 2021, I wasn’t confident about how I was coming across to others. Self-conscious, I overcompensated and came on too strong. I made mistakes about what to share in what settings. Later on, I tried to repair relationships that hadn’t started out on the right foot. In many cases, rebooting led to restoring. In some cases, however, it didn’t, and in those cases, I beat up on myself. Finding my footing and regaining strength took a long time.

In the musical, Hamilton, Eliza is the embodiment of grace. Alexander’s long-suffering wife, whom he loves but betrays, sings words I find so beautiful they always bring me to tears: “I don’t pretend to know the challenges you’re facing” in one breath, and “I’m not afraid; I know who I married” in another. That combination of, “I know you and love you,” with, “I empathize even with the parts of you I don’t understand,” provide guidance for how we are supposed to treat one another in-community.

There are two sets of values I try to take into every conversation I have in my leadership role: (1) I take the concerns of those around me, especially those in my direct care, seriously; and (2) I appreciate that people in my community have commitments and concerns to deal with that go beyond what I know. I don’t always succeed in upholding these values, but I believe in them. As a person who educates leaders, I sometimes feel I ought to be doing much more to hold up these values to students, as I’m not sure where else they’re learning how to be together in-community.

I support students’ rights to protest. I believe in the cause of insisting that our government use every lever it has at-hand to press for a cease-fire on Gaza, first by refraining from sending weapons that kill. What saddens me about the protests we’re witnessing is the atmosphere of estrangement surrounding them. Students don’t seem motivated to understand what would get their administrations to concede to their demands. Administrators have fallen so far out of relationship with students that they stereotype and categorize; students become problems, not people.

Boeing safety protocols seem to have gone wrong around the same point in time when it moved its business headquarters away from its manufacturing plant. In a similar way, college and university administrators, removed from the educational function of the faculty, lose track of the promises universities made to students: we told you that, if you come here, we’ll teach you about how to be in-community. One requirement for being together? That all strive toward generosity in extending grace, understanding, the benefit of the doubt to one another.

How do we teach future ministers and other community leaders about generosity? Hall modeled it, and then challenged gift recipients to try it out. I can take a page out of his book, modeling generous empathy and encouraging students to be understanding toward others, including both their peers and their leaders. When they come to me complaining about a leader who’s disappointed them, I can’t fix how they feel about that other leader. I can, however, model generous empathy in how I talk to them about their own concerns, which don’t fully understand, but which I know are important.

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Sarah B. Drummond

Sarah Birmingham Drummond is Founding Dean of Andover Newton Seminary at Yale Divinity School and teaches and writes on the topic of ministerial leadership.