No matter how you frame it, we’ve professionalized, optimized, and branded our way into stagnation and retreat. We treated the gift like an input in a machine.
The below article originally appeared on March 24, 2025, in The Butterfly Effect on Substack.
***
I have a hunch. With political instability, economic anxiety, and confidence wearing thin, another wave of philanthropic reform is just around the corner. Much of what we promised would work will prove ill-suited for the road ahead. New frameworks will be unveiled. New champions will be picked. Buzzwords—equity, accountability, transformation—will return with new urgency. There will be panels, initiatives, and manifestos, all insisting that this time, the changes will stick.
Here’s what I’ve observed: the things we try to reform are rarely the ones that matter most. Reform tends to fixate on what can be measured, managed, and credited—where reformers still believe control is within reach—while quietly avoiding what they don’t understand, where control is harder to find. And nothing, I’d argue, is more misunderstood—or more resistant to control—than the gift.
So here’s my suggestion: before we sign on to another well-meaning campaign to fix philanthropy, let’s slow down and consider what we’ve spent decades overlooking. Reform, for all its good intentions, often leaves behind more mess than meaningful change—especially when it tinkers with surface-level systems while ignoring the deeper forces that animate them. For now, let’s turn our attention to what we always invoke but rarely take the time to understand.
Anyone who denies the mess we’re in has every right to. They can disagree with my take on where philanthropy stands—but I’m reading the same reports they are: declining donor retention, eroding trust, a growing concentration of resources, and a widening gap between funders and the communities they claim to serve. I’m not saying it’s a failure of effort. It’s a failure of understanding—not of modern inventions like institutional philanthropy or professional fundraising, but of the gift itself.
No matter how you frame it, we’ve professionalized, optimized, and branded our way into stagnation and retreat. We treated the gift like an input in a machine. The Trump administration didn’t create these problems—it just exposed how fragile and over-engineered the system already was. And now we’re surprised the gift isn’t cooperating. Instead of rewarding our supposedly enlightened efforts at social engineering, it resists—refusing to give us the satisfaction of scaling it up.
The age of reform was an age of control
I picked up a copy of David Graeber’s The Utopia of Rules about six months ago. Just a few pages in, I found myself thinking about philanthropy—not as a timeless human impulse, but as one of several twentieth-century reform movements similar to the waves of educational reform, religious moralism, or technocratic management that came before it. Like the rest, philanthropy promised progress. What it delivered was structure, standardization, and more ways to manage what wants to move freely and without constraint.
Graeber’s central point is hard to miss: modern bureaucracies weren’t built on rational efficiency so much as on a deep fear of unpredictability, messiness, and complexity. Bureaucracy, he argues, is what we reach for when we can’t fully understand or contain what we’re dealing with. And, if you zoom out far enough, you see the same pattern again and again; reform movements aimed at alcohol, education, labor, and morality all followed the same playbook. When something powerful refused to cooperate, we didn’t try to understand it—we built systems to constrain it. Not out of wisdom, but fear.
Similarly, political scientist James C. Scott, in Seeing Like a State, shows how many of these efforts were fueled by what he calls high modernism—the belief that society could be improved through centralized planning, technical expertise, and rational design. Where Graeber critiques bureaucracy as a coping mechanism, Scott shows how it became an ideology. These projects didn’t start with understanding. They started with control. And philanthropy, true to form, followed that same path—trading the messy, relational nature of the gift for legibility, manageability, and performance.
We don’t get philanthropy as we know it today without someone first deciding the gift was beyond their control. From there, it was steadily distorted—governed by rules, tracked through data, disguised as performance, or expressed as individualism. That’s what the modern philanthropic system is built to do: maneuver the gift toward outcomes it was never meant to serve. These systems weren’t designed to enhance the experience of giving. They were designed to contain it. And, the more the gift resists domestication, the more control we try to impose.
Philanthropy followed the same formula as every other reform project before it. A universal, deeply human impulse got absorbed into a system of tax codes, strategic plans, event calendars, and choreographed campaigns. It wasn’t the result of evolution. It was reform by accumulation—layer by layer—driven by anxiety over inefficiency, unpredictability, and the terrifying prospect of losing control. And, now, like so many reform efforts before it, we’re left with a system so focused on doing things by the book that we can’t remember what the gift has always known how to do—long before the book was written.
Philanthropy as a reform movement
What we now call philanthropy—the late-twentieth-century version funded by private foundations, governed by boards, and executed by professional fundraisers—didn’t grow out of a deep understanding of human behavior. It grew out of a need to manage it. In the decades after the Civil Rights Movement, as wealth accumulated, the state pulled back from its obligations, and the nonprofit sector ballooned, something emerged that looked like philanthropy but was really something else: a reform movement built to impose order on something that never asked for it.
Now, to be fair: philanthropy didn’t set out to betray the gift. But it was built on a bad assumption—that the gift could be improved by designing systems around it. So we built strategies, metrics, giving vehicles, and grant cycles—not to expand the gift’s power, but to domesticate it. We replaced trust with accountability, spontaneity with planning, and relationship with reporting. And, until recently—like all good reformers—we convinced ourselves that getting in the way was the same as making it better.
Graeber warned us: bureaucracy rarely solves the problems it claims to address. More often, it makes them harder to solve. That’s where philanthropy finds itself now. It’s not that people don’t want to give. It’s that the gift, once offered freely, is now so monitored, managed, and controlled that it can barely breathe. We didn’t improve anything. We boxed it in—and somewhere along the way, we lost sight of what made the gift a gift in the first place.
Which is why, before the next wave of reform inevitably rolls in promising to fix what the last wave couldn’t, we should pause and remember what most of us, deep down, already know but have been trained to forget.
The gift moves
The first fundamental of a gift is simple: it has to move. It can’t be stockpiled, stalled, or delayed without losing something essential to its nature. A gift only reveals its meaning in motion. The moment we try to hold it, hedge it, or wait for the “right” conditions, it starts to morph—becoming more cautious, more strategic, and less alive.
No one has institutionalized stagnation more effectively than Big Philanthropy—not just private foundations, but university endowments, donor-advised funds, and intermediaries with vast resources and tightly scripted processes. Massive sums sit largely untouched. Payout rates hover at the legal minimum. Program officers spend months reviewing proposals for funding that may never come. The wealth moves in—but the gift doesn’t move out.
This isn’t stewardship—it’s fear. Fear that if the gift moved freely, it might end up somewhere unexpected. It might create obligations we didn’t plan for. It might bind us to people we weren’t prepared to trust. So we build systems to manage the risk. But the gift doesn’t hedge its bets. It moves where it’s needed. And, when we try to force it into submission, it doesn’t just slow down—it disappears.
The gift creates a relationship
If the first fundamental is most often betrayed by those with excess—institutions better at preserving wealth than releasing it—the second is usually betrayed by those trying to reach the many. For the last half-century, the everyday donor’s experience has been defined not by relationship, but by confinement to a mailing list.
The second fundamental is this: the gift creates a relationship. That’s its purpose. It’s not a financial exchange; it’s a relational act. A gift binds people together. It carries memory, meaning, and trust. It invites reciprocity—not through obligation, but through mutual care. When that happens, the gift becomes more than a transaction. It becomes a connection.
But that’s exactly what many of my fundraising colleagues have tried to bypass. Nowhere is this more obvious than in the world of direct response and its digital descendants. The name alone gives it away. These systems weren’t built to foster relationships; they were built to trigger impulsive, consumer-like reactions. Donors are segmented, targeted, messaged, and asked—again and again—on carefully timed cycles optimized for response, not connection.
Those who’ve championed this approach are notorious for rationalizing what counts as a relationship. But, if they were honest, they wouldn’t accept the same standard anywhere else. In any other setting, a one-sided, one-directional dynamic—where one party never shows up, never reciprocates, never even acknowledges the giver—wouldn’t pass for a relationship at all.
So maybe it’s time to stop rationalizing and tell the truth: authentic gift relationships are expensive, inefficient, and hard to control. And, instead of doing the slower, riskier work of building real connection, we expect the everyday donor to settle for something else.
The gift must be free
If the first fundamental is most often betrayed by those who preserve wealth, and the second by those who exploit the well-meaning, everyday donor, the third is felt by all of us—on both ends of the spectrum and everywhere in between.
The third fundamental is often the most unsettling for modern reformers: the gift is free. It can’t be coerced, extracted, or expected. It has to be given freely—and received freely. The moment we try to enforce it—morally, politically, or institutionally—it stops being a gift. The gift doesn’t ask for permission. It disappears the moment we give it a script, calculate its fairness, or dictate its direction.
Yet this is exactly where so many reform efforts go wrong. They try to secure the gift through obligation rather than relationship. What should be an act of trust becomes a duty, a commodity, a performance, or a gesture of individualism. The gift loses its freedom to move or surprise; it’s forced to conform, to prove its worth, to follow the script. And, in the process, it loses the very qualities that made it a gift in the first place.
The gift isn’t a virtue signal. It’s not proof of enlightenment. And it certainly can’t be summoned by shame. The more we try to manage its meaning, the more it retreats. What we’re left with is compliance, not connection. And, no matter how urgent the cause or how noble the intention, once the gift loses its freedom, it loses its power.
The question history will ask
The reformers of the twentieth century didn’t set out to screw up what they tried to fix. But, again and again, they mistook what was unfamiliar—or simply more powerful than they were—for something broken. Every time they encountered something messy or unpredictable, they assumed managing it was the same as improving it. So they built bureaucracies and rules, convinced they were fixing a problem. More often than not, they were just interfering with something they didn’t understand.
Philanthropy followed the same path. What should have remained a space for freedom, connection, and movement became another reform project. We organized it. We optimized it. We buried it under policies, metrics, and multi-step engagement strategies. And now we find ourselves asking why the gift feels so elusive, so out of touch, so unresponsive. But maybe that’s not the gift. Maybe that’s just what we’ve turned it into.
We can only wonder how this era will be remembered. Will everything we’ve built—largely since the Civil Rights movement—be seen as a bold transformation of generosity? Or will it look like yet another failed reform movement, one that tried to manage what it never truly understood—and, in doing so, got in the way?
The gift doesn’t need reform
If anything needs reform, it isn’t the gift. It’s us. We’re the ones who lost the plot. We’re the ones who decided the gift needed our intervention. We’re the ones who mistook management for meaning and strategy for substance. We didn’t make the gift stronger. We made it harder to find.
The fundamentals still hold: the gift must move, the gift creates a relationship, and the gift must be free. These aren’t romantic notions or nostalgic ideals—they’re what make a gift a gift. And, when we violate them—even in the name of efficiency or justice—we’re not modernizing the gift; we’re replacing it with something else.
As I said at the outset, it’s only a matter of time before the next round of reforms is proposed to fix whatever philanthropy is accused of getting wrong now. But philanthropy doesn’t need more reform. It needs to let go of its modern, enlightened attempts to manage what never needed controlling in the first place. Instead of getting in its way, we need to create environments where the gift can move freely and without constraint.
As Graeber reminded us, “The ultimate, hidden truth of the world is that it is something we make, and could just as easily make differently.” The problem isn’t the gift; it’s the world we’ve built around it. And, if we made that world, we can unmake it too.
