Essay 2: The Prerequisite for Courage
This is the second essay in Taming the Gift, a series exploring the limits of contemporary fundraising and what it will take to recover the wild, unpredictable power of the gift. To learn more about the project, visit here.
When Ezra Klein told a room of philanthropic leaders that civil society had been “a horrifying disappointment,” he was not describing apathy, ignorance, or a lack of resources. He was describing something more unsettling: a civil society that understood what was happening, possessed the means to respond, enjoyed deep legitimacy, and still hesitated when action carried consequence.1
Speaking at the Center for Effective Philanthropy’s annual conference in Los Angeles, Klein described a landscape that I suspect feels familiar to many of us who work near power. He pointed to business leaders who adjusted their posture rather than confront authority, to law firms that recalibrated their commitments, and to universities that waited for someone else to move first. His language was sharp, even moral. He spoke about courage and cowardice, about institutions that should have acted and did not.
Then he asked the question that I imagine lingered over the room: What is the point of all this money if it doesn’t give you independence? What is the point of these huge endowments if they don’t give freedom of movement?
Klein is not a foundation leader. He’s a journalist and podcaster who was speaking to 600 philanthropic leaders and donors who were no doubt familiar with his work. Klein was invited as an observer of our sector. The question is whether an observer can see everything; or whether he, too, might be swimming in water he can’t name. He could see a pattern that many of us working inside this world live daily but struggle to articulate. It’s the same problem Wallace described with his two fish: the most obvious, important realities are often the ones hardest for us to see.
What Klein named as a disappointment has been observed before. James C. Scott called it an incapacitated civil society—institutions that remain structurally intact while losing autonomous capacity to act. Foucault described it as governmentality, Tocqueville as soft despotism—power operating through administration and care rather than force, keeping citizens engaged in sanctioned forms of activity while constraining independent action. In each case, institutions lose their independence not through force but through arrangement. They remain intact while becoming unable to act on their own authority.
Domestication Without Collapse
What Klein observed is the condition we described in our opening essay: ours is a tame sector. He observes and criticizes it from his perch at the New York Times; many in that room likely felt it from within. We remain present, professional, and engaged, yet increasingly constrained in our ability to act independently when action involves risk. This is not a story of collapse or corruption. It is a story of capacity that has been preserved in form while narrowed in practice.
Klein was speaking to leaders like many of us—people operating inside institutions designed for stability, continuity, and legitimacy. When asked what he wanted to see, his answer was blunt: “I would like to see the people who lead important parts of civil society not be cowards.” The paradox he named was not why we lack values, but why we seem unable to act on them.
Incapacitation helps clarify what we’re experiencing. Incapacity does not mean silencing, dismantling, or defunding. It describes organizations that remain active, visible, and institutionally intact while losing the freedom of movement required to exercise judgment without prior authorization. Many of us know this feeling: the instinct to ask permission before acting, even when we have the authority—to check with the board, run it by legal, get sign-off from funders, not necessarily because the rules require it but because independent action feels dangerous. We continue to function. Moral language continues to circulate. What isn’t there is autonomy at a moment when it matters most.
But the interviewers didn’t ask the harder question— the one that would have implicated everyone in that room, themselves included: What does it say about a society that requires every action be recorded in a CRM, added to a board report, and reviewed by a program officer at MacArthur? And who convinced us all that this was how social change actually works?
Legibility as a Way of Knowing
The question, then, is not why we lack courage. It is what produces a system in which courage becomes so risky and expensive. To answer that, we need to remember what we’re looking for—the default settings. We need to swim further upstream, past the visible symptoms Klein described, closer to the source.
The answer lies in a worldview so familiar it rarely appears as a worldview at all: legibility. As Scott would say, it’s “seeing like the state” in ways that ensure functions like “taxation, conscription, and prevention of rebellion.” Legibility makes society readable from above, transforming the messy, context-dependent texture of actual life into forms that can be administered from a distance. Importantly, legibility is not about seeing more. It is about arranging reality so it can be seen in particular ways and then making everything else disappear. Legibility doesn’t just treat different people, places, and ways of life as if they were the same; it creates an environment that encourages us to forget those differences ever existed.2
The concept may be unfamiliar, but its effects are everywhere. Those of us working in modern institutions operate on the assumption that complex social realities must be made legible before they can be trusted or improved. Legibility enables comparison; comparison enables ranking; ranking enables management. What cannot be rendered legible—arranged into standard categories, measured by common metrics, explained to distant observers—cannot be justified. What cannot be justified struggles to be funded, governed, or defended.
What I’ve noticed is how legibility trains us to believe that responsibility begins with visibility, that legitimacy requires justification in advance, that action must be defensible before it is taken. As more of us organized around what could be seen and compared from above, what Scott calls metis—the local knowledge, practical wisdom, and context-dependent judgment that actually makes things work—becomes suspect. This posture feels serious, ethical, and prudent until crisis makes the world more complex and legibility impossible.
Over time, legibility hardens into infrastructure. 990s, grant applications, evaluation frameworks, CRMs, dashboards, and reporting cycles become so routine that they barely register as choices. Like a map that slowly replaces the terrain, these tools begin to stand in for the work itself. They don’t just describe what we do; they arrange our work into forms that can be seen, compared, and managed from above.
Klein’s Own Legibility Project
Klein posed a question at CEP: Why won’t civil society act with courage? Why do institutions with resources, values, and legitimacy hesitate when action carries risk? He saw it as a moral failure—a lack of courage in the face of crisis.
Just weeks later, Klein sat down with Elie Hassenfeld, the co-founder and CEO of GiveWell, for a New York Times opinion piece. Klein was enthusiastic: “Out of every organization I have known, I have the most trust in GiveWell to do the vetting, to run the experiments, to read the research—to really figure out where my money will go the farthest.”3
GiveWell and similar effective altruism-oriented endeavors represent legibility logic in its purest form. Hassenfeld started the organization in 2007 after discovering what many of us have experienced: charitable organizations couldn’t answer basic questions about their effectiveness. Organizations would promise things like, “Twenty dollars provides a child water for life,” but couldn’t explain how or prove it. For donors, this created uncertainty, exposure, and the terrifying possibility of being wrong.
GiveWell’s methodology relies on randomized controlled trials, calculating cost-effectiveness in dollars per death averted, then ranking organizations. The promise: make charity legible, and donors can give with confidence.
But here’s what Klein doesn’t see: he just answered his own question.
When describing why GiveWell was necessary, Hassenfeld revealed exactly what the absence of legibility creates—hesitation and fear. What Klein experienced as a donor was uncertainty that felt paralyzing until GiveWell made giving legible.
This is exactly what civil society leaders experience when Klein asks them to act courageously in crisis. The world becomes illegible—metrics disappear, outcomes become uncertain, dashboards stop working. Without legibility, action feels reckless. Klein saw hesitation in the CEP room and called it cowardice. He felt hesitation as a donor and called it due diligence. But it’s the same hesitation produced by the same logic. We have been trained to believe that acting without confidence is irresponsible.
The absence of legibility doesn’t create courage. It creates exactly what Klein criticized: institutions that understand the problem, possess resources, enjoy legitimacy, and still cannot move. Klein observed the domestication of civil society while advocating for the domestication of giving. He diagnosed the symptom while championing the cause.
How Legibility Redirects Risk
Being made legible does not stop action. It redirects it. Over time, justification replaces discernment. We internalize legibility systems until legitimacy itself becomes something that must be continuously produced through display.
This creates a tension I suspect many of us have felt. We resent being flattened when we are the ones being observed from above—when a grant application misses the point or an evaluation captures everything except what matters. Yet we rely on the same systems when we need to demonstrate effectiveness, secure funding, or protect ourselves. We are simultaneously its victims and its enforcers.
Legibility systems change where knowledge lives. Knowledge that once existed in bodies, in relationships, in the felt sense of working alongside someone, migrates into databases, reports, and profiles. When that abstract knowledge is trusted more than embodied judgment—when the profile is more real than the person—the transformation is complete.
This helps explain what Klein was describing: a sector that is morally awake, well resourced, and highly articulate, yet hesitant precisely when action carries consequence. What looks like cowardice often reflects rational adaptation to a regime of legibility. None of this requires bad actors. It emerges from a worldview that equates responsibility with explainability and seriousness with measurement.
The First Default Setting
This is the first default setting. Everything that matters must be seen. Legibility becomes the price of legitimacy. And, once reality is rendered legible, it no longer simply appears. It becomes available for interpretation, judgment, and control.
Being seen is only the beginning. Once our work is visible, it does not remain merely observed. It becomes manageable. That is where the next default setting emerges: someone has to be in charge.
- Jason Lewis, Partner & Chief Innovation Officer at Seed
Taming the Gift is a collaboration with Seed, born of a shared commitment to understanding the limits of contemporary fundraising and to reimagining practices that activate cultures of wild generosity.
Scott, J. C. (2020). Seeing Like a State: How Certain Schemes to Improve the Human Condition Have Failed. United States: Yale University Press.